You are cordially invited to attend a special meeting of the stockholders of ProAssurance Corporation (“ProAssurance”). The special meeting will be held at 9:00 a.m., Central Daylight Time, on Tuesday, June 24, 2025, in the O’Neil Multimedia Room at the headquarters of ProAssurance, located at 100 Brookwood Place, Birmingham, Alabama 35209 (the “special meeting”).

At the special meeting, ProAssurance stockholders will be asked to consider and vote on a proposal to adopt the Agreement and Plan of Merger, dated as of March 19, 2025 (as amended or modified from time to time, the “merger agreement”), among ProAssurance, The Doctors Company, and Jackson Acquisition Corporation, a wholly owned subsidiary of The Doctors Company (“Merger Sub”). Subject to the terms and conditions of the merger agreement, Merger Sub will be merged with and into ProAssurance, the separate existence of Merger Sub will cease, and ProAssurance will survive the merger as a wholly owned subsidiary of The Doctors Company (the “merger”).

If the merger is completed, ProAssurance stockholders will have the right to receive $25.00 in cash, without interest and subject to any applicable withholding taxes, for each share of common stock, par value $0.01 per share, of ProAssurance (“ProAssurance common stock”), other than cancelled shares, non-cancelled subsidiary shares and dissenting shares (each as defined in the accompanying proxy statement), that they own immediately prior to the effective time of the merger, which represents a premium of approximately 58.8% over ProAssurance’s closing stock price on March 18, 2025, the last trading day prior to the announcement of the merger agreement. Approval of the proposal to adopt the merger agreement requires the affirmative vote (in person or by proxy) of the holders of a majority of the outstanding shares of ProAssurance common stock entitled to vote as of the close of business on the record date (as defined in the accompanying proxy statement).

ProAssurance common stock is listed on the New York Stock Exchange (“NYSE”) under the symbol “PRA”. The closing price of ProAssurance common stock on NYSE on Tuesday, May 13, 2025, the latest practicable date before the printing of the accompanying proxy statement, was $23.00 per share.

The ProAssurance board of directors (the “ProAssurance Board”) has reviewed and considered the terms of the merger and has (a) approved and declared advisable the merger agreement and the transactions contemplated thereby, including the merger, (b) determined that the merger agreement and the transactions contemplated thereby, including the merger, are in the best interests of ProAssurance and the ProAssurance stockholders, (c) directed that the merger agreement be submitted to the ProAssurance stockholders for adoption and (d) recommended that the merger agreement be adopted by the ProAssurance stockholders. The ProAssurance Board made its determination after consultation with its outside legal counsel and its financial advisors and consideration of various factors, as more fully described in the accompanying proxy statement.

The ProAssurance Board unanimously recommends that you vote “FOR” the proposal to adopt the merger agreement.

At the special meeting, stockholders will also be asked to vote on (a) a proposal to approve, on a non-binding, advisory basis, certain compensation that will or may be paid by ProAssurance to its named executive officers based on or otherwise relating to the merger, as required by the rules adopted by the U.S. Securities and Exchange Commission (the “named executive officer merger-related compensation proposal”), and (b) a proposal to adjourn the special meeting from time to time, if necessary, as determined in good faith by the ProAssurance Board, including for the purpose of soliciting additional votes for the approval of the merger proposal if there are insufficient votes at the time of the special meeting to approve the proposal to adopt the merger agreement by ProAssurance stockholders (the “adjournment proposal”). The ProAssurance Board unanimously recommends that you vote “FOR” each of these proposals.

The ProAssurance Board is soliciting your proxy to ensure that a quorum is present and that your shares are represented and voted at the special meeting and any postponement or adjournment thereof.

If your shares are held in “street name,” you should instruct your broker, bank or other nominee how to vote your shares on each proposal in accordance with your voting instruction form.

The merger cannot be completed unless ProAssurance stockholders adopt the merger agreement. Your vote is very important, regardless of the number of shares you own. Whether or not you expect to attend the special meeting, please submit a proxy to vote your shares as promptly as possible to ensure that your shares may be represented and voted at the special meeting. If you receive more than one proxy card because you own shares registered in different names or addresses, each proxy should be submitted. If you attend the special meeting and vote in person, your in person vote will revoke any proxy previously submitted. If you fail to either return your proxy or attend the special meeting and vote in person, your shares will not be counted for purposes of determining whether a quorum is present at the special meeting and will have the same effect as a vote “AGAINST” the adoption of the merger agreement. Similarly, if you hold your shares in “street name” and fail to instruct your broker, bank or other nominee how to vote your shares, your shares will not be counted for purposes of determining whether a quorum is present and will have the same effect as a vote “AGAINST” the adoption of the merger agreement.

The obligations of ProAssurance, The Doctors Company and Merger Sub to complete the merger are subject to the satisfaction or waiver of certain conditions. The accompanying proxy statement contains detailed information about ProAssurance, the special meeting, the merger agreement, the merger, the named executive officer merger-related compensation proposal and the adjournment proposal. A copy of the merger agreement is attached as Annex A to the accompanying proxy statement and incorporated therein by reference. ProAssurance urges you to, and you should, read the entire proxy statement carefully, including the merger agreement and the other annexes and the documents referred to or incorporated by reference in the accompanying proxy statement. You may obtain additional information about ProAssurance from documents it has filed with the U.S. Securities and Exchange Commission.

If you have any questions or need assistance voting your shares of ProAssurance common stock, please contact Okapi Partners LLC, ProAssurance’s proxy solicitor, by calling (855) 305-0857 (toll-free) or (212) 297-0720 (banks and brokers).

Neither the U.S. Securities and Exchange Commission nor any state securities regulatory agency has approved or disapproved of the merger, passed upon the merits of the merger agreement or the merger or determined if the accompanying proxy statement is accurate or complete. Any representation to the contrary is a criminal offense.

The accompanying proxy statement is dated May 14, 2025 and, together with the enclosed form of proxy card, is first being mailed to ProAssurance stockholders on or about May 14, 2025.

YOUR VOTE IS VERY IMPORTANT, REGARDLESS OF THE NUMBER OF SHARES YOU OWN. WHETHER OR NOT YOU EXPECT TO ATTEND THE SPECIAL MEETING, PLEASE SUBMIT A PROXY TO VOTE YOUR SHARES OVER THE INTERNET OR BY TELEPHONE PURSUANT TO THE INSTRUCTIONS CONTAINED IN THESE MATERIALS OR COMPLETE, DATE, SIGN AND RETURN A PROXY CARD AS PROMPTLY AS POSSIBLE TO ENSURE THAT YOUR SHARES MAY BE REPRESENTED AND VOTED AT THE SPECIAL MEETING. IF YOU RECEIVE MORE THAN ONE PROXY CARD BECAUSE YOU OWN SHARES REGISTERED IN DIFFERENT NAMES OR ADDRESSES, EACH PROXY SHOULD BE SUBMITTED. IF YOU ATTEND THE SPECIAL MEETING AND VOTE IN PERSON, YOUR IN PERSON VOTE WILL REVOKE ANY PROXY PREVIOUSLY SUBMITTED. IF YOU FAIL TO EITHER RETURN YOUR PROXY OR ATTEND THE SPECIAL MEETING AND VOTE IN PERSON, YOUR SHARES WILL NOT BE COUNTED FOR PURPOSES OF DETERMINING WHETHER A QUORUM IS PRESENT AT THE SPECIAL MEETING AND WILL HAVE THE SAME EFFECT AS A VOTE “AGAINST” THE ADOPTION OF THE MERGER AGREEMENT. SIMILARLY, IF YOU HOLD YOUR SHARES IN “STREET NAME” AND FAIL TO INSTRUCT YOUR BROKER, BANK OR OTHER NOMINEE HOW TO VOTE YOUR SHARES, YOUR SHARES WILL NOT BE COUNTED FOR PURPOSES OF DETERMINING WHETHER A QUORUM IS PRESENT AND WILL HAVE THE SAME EFFECT AS A VOTE “AGAINST” THE ADOPTION OF THE MERGER AGREEMENT.

Your proxy may be revoked at any time before the vote at the special meeting by following the procedures outlined in the accompanying proxy statement.

If you are a beneficial owner of shares held by a broker, bank or other nominee and you wish to vote in person at the special meeting, you must bring to the special meeting a proxy from the broker, bank or other nominee that holds your shares authorizing you to vote in person at the special meeting.

If your shares of ProAssurance common stock entitled to vote are registered directly in your name, you are considered the holder of record with respect to such shares of ProAssurance common stock and you have the right to attend the special meeting and vote in person. If you decide to attend the special meeting in person, please be prepared to provide proper identification, such as a driver’s license.

If your shares of ProAssurance common stock entitled to vote are held in a brokerage account or by a bank or other nominee, you are the beneficial owner of such ProAssurance common stock. As such, in order to vote at

the special meeting, you must follow the instructions provided by your bank, brokerage firm or nominee. Additionally, if you decide to attend the special meeting in person, you will need to provide proof of ownership, such as a recent account statement or voting instruction form provided by your bank, broker or other nominee or other similar evidence of ownership, along with proper identification.

The proxy statement of which this notice forms a part provides a detailed description of the merger, the merger agreement, the named executive officer merger-related compensation proposal and the adjournment proposal, and provides specific information concerning the special meeting. ProAssurance urges you to read the proxy statement, including any documents incorporated therein by reference, and its annexes carefully and in their entirety. If you have any questions concerning the merger or the proxy statement, would like additional copies of the proxy statement or need help voting your shares of ProAssurance common stock, please contact ProAssurance’s proxy solicitor, Okapi Partners LLC.

The following are brief answers to certain questions that you may have regarding the merger, the special meeting and the proposals being considered at the special meeting. ProAssurance urges you to carefully read the remainder of this proxy statement because the information in this section does not provide all of the information that might be important to you with respect to the merger and the special meeting. Additional important information is also contained in the annexes attached to this proxy statement and the documents referred to or incorporated by reference into this proxy statement.

This proxy statement contains “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Exchange Act. These statements are often identified by the use of words such as “anticipate,” “believe,” “continue,” “could,” “estimate,” “expect,” “intend,” “may,” “plan,” “hope,” “hopeful,” “likely,” “may,” “optimistic,” “possible,” “potential,” “preliminary,” “project,” “should,” “will,” “would” or the negative or plural of these words or similar expressions or variations. Forward-looking statements are made based upon management’s current expectations and beliefs and are not guarantees of future performance. Such forward-looking statements are subject to a number of risks, uncertainties, assumptions and other factors that could cause actual results and the timing of certain events to differ materially from future results expressed or implied by the forward-looking statements. These factors include, among others: (a) the completion of the merger on the anticipated terms and timing, (b) the satisfaction of other conditions to the completion of the merger, including obtaining required shareholder and regulatory approvals; (c) the risk ProAssurance’s stock price may fluctuate during the pendency of the merger and may decline if the merger is not completed; (d) potential litigation relating to the merger that could be instituted against ProAssurance or its directors, managers or officers, including the effects of any outcomes related thereto; (e) the risk that disruptions from the merger will harm ProAssurance’s business, including current plans and operations, including during the pendency of the merger; (f) the ability of ProAssurance to retain and hire key personnel; (g) the diversion of management’s time and attention from ordinary course business operations to completion of the merger and integration matters; (h) potential adverse reactions or changes to business relationships resulting from the announcement or completion of the merge; (i) legislative, regulatory and economic developments; (j) potential business uncertainty, including changes to existing business relationships, during the pendency of the merger that could affect ProAssurance’s financial performance; (k) certain restrictions during the pendency of the merger that may impact ProAssurance’s ability to pursue certain business opportunities or strategic transactions; (l) unpredictability and severity of catastrophic events, including but not limited to acts of terrorism, outbreaks of war or hostilities or global pandemics, as well as management’s response to any of the aforementioned factors; (m) the possibility that the merger may be more expensive to complete than anticipated, including as a result of unexpected factors or events; (n) unexpected costs, liabilities or delays associated with the transaction; (o) the response of competitors to the transaction; (p) the occurrence of any event, change or other circumstance that could give rise to the termination of the merger, including in circumstances requiring ProAssurance to pay a termination fee; and (q) other risks set forth under the heading “Risk Factors,” of our Annual Report on Form 10-K for the year ended December 31, 2024 and in our subsequent filings with the SEC. You should not rely upon forward-looking statements as predictions of future events. Our actual results could differ materially from the results described in or implied by such forward looking statements. Forward-looking statements speak only as of the date hereof, and, except as required by law, we undertake no obligation to update or revise these forward-looking statements.

ProAssurance is an industry-leading specialty insurer with extensive expertise in medical professional liability and products liability for medical technology and life sciences. ProAssurance also is a provider of workers’ compensation insurance in the eastern U.S. ProAssurance is rated “A” (Excellent) by AM Best.

The ProAssurance common stock is traded on NYSE under the ticker symbol “PRA”.

ProAssurance’s principal executive offices are located at 100 Brookwood Place, Birmingham, Alabama 35209, and ProAssurance’s telephone number is (800) 282-6242. ProAssurance’s corporate web address is www. proassurancegroup.com. The information provided on ProAssurance’s website is not part of this proxy statement and is not incorporated in this proxy statement by reference or by any other reference to ProAssurance’s website provided in this proxy statement.

Additional information about ProAssurance is contained in its public filings with the SEC, which filings are incorporated by reference herein. See the section of this proxy statement entitled “Where You Can Find Additional Information” beginning on page 108.

The Doctors Company, founded and led by physicians, is the nation’s largest physician-owned medical malpractice insurer, is relentlessly committed to advancing, protecting, and rewarding the practice of good medicine. The Doctors Company helps all healthcare providers manage the complexities of today’s healthcare environment—with expert guidance, resources, and coverage. The Doctors Company is part of TDC Group (tdcg.com), the nation’s largest physician-owned provider of insurance and risk management solutions. TDC Group serves the full continuum of care, from individual clinicians to academic medical systems—with over 110,000 healthcare professionals and organizations nationwide—with annual revenue of $1.5 billion and more than $8 billion in assets.

Merger Sub is a wholly owned subsidiary of The Doctors Company and was formed on March 14, 2025, solely for the purpose of engaging in transactions of the nature contemplated by the merger agreement and has not engaged in any business activities other than in connection with the transactions contemplated by the merger agreement.

This proxy statement is being provided to ProAssurance stockholders as part of a solicitation by the ProAssurance Board for proxies for use at the special meeting, to be held at the time and place specified below, and at any properly convened meeting following an adjournment or postponement of the special meeting.

The special meeting is scheduled to be held at 9:00 a.m., Central Daylight Time, on June 24, 2025, in the O’Neil Multimedia Room at the headquarters of ProAssurance, located at 100 Brookwood Place, Birmingham, Alabama 35209.

At the special meeting, ProAssurance stockholders will be asked to consider and vote on the following proposals:

The adoption of the merger agreement by the affirmative vote of holders of a majority of the outstanding shares of ProAssurance common stock entitled to vote as of the close of business on the record date is a condition to the completion of the merger. If ProAssurance stockholders fail to approve the merger proposal, the merger will not occur.

The vote on the named executive officer merger-related compensation proposal is a vote separate and apart from the vote to approve the merger proposal. Accordingly, a stockholder may vote to approve the merger proposal and vote not to approve the named executive officer merger-related compensation proposal, and vice versa. Because the vote on the named executive officer merger-related compensation proposal is only advisory in nature, it will not be binding on ProAssurance, The Doctors Company or the surviving corporation. Accordingly, because ProAssurance is contractually obligated to pay such merger-related compensation, the compensation will be payable, subject only to the conditions applicable thereto, if the merger proposal is approved, regardless of the outcome of the advisory vote.

Other than the matters described above, ProAssurance does not expect a vote to be taken on any other matters at the special meeting or any adjournment or postponement thereof, and ProAssurance has agreed in the merger agreement that no other matters (other than customary procedural matters) shall be brought before the special meeting.

The ProAssurance Board has reviewed and considered the terms and conditions of the proposed merger. After consultation with its outside legal counsel and its financial advisors and after consideration of various factors, as more fully described in this proxy statement, the ProAssurance Board has (a) approved and declared advisable the merger agreement and the transactions contemplated thereby, including the merger, (b) determined that the merger agreement and the transactions contemplated thereby, including the merger, are in the best interests of ProAssurance and the ProAssurance stockholders, (c) directed that the merger agreement be submitted to the ProAssurance stockholders for adoption and (d) recommended that the merger agreement be adopted by the ProAssurance stockholders. Certain factors considered by the ProAssurance Board in reaching its

decision to adopt the merger agreement can be found in the section of this proxy statement entitled “The Merger Proposal (Proposal 1)—Recommendation of the ProAssurance Board and Reasons for the Merger” beginning on page 44.

The ProAssurance Board unanimously recommends that ProAssurance stockholders vote “FOR” the merger proposal, “FOR” the named executive officer merger-related compensation proposal and “FOR” the adjournment proposal.

Only holders of record of ProAssurance common stock at the close of business on May 12, 2025, the record date for the special meeting, will be entitled to notice of, and to vote at, the special meeting or any adjournments or postponements of the special meeting.

Holders of record of ProAssurance common stock are entitled to one vote for each share of ProAssurance common stock they own of record at the close of business on the record date. At the close of business on the record date, there were 51,070,243 shares of ProAssurance common stock issued and outstanding, held by approximately 2,154 holders of record.

Under ProAssurance’s bylaws, the presence, in person or represented by proxy, at the special meeting of holders of shares of common stock having one-third of the votes which could be cast by holders of all outstanding shares of ProAssurance common stock entitled to vote thereat at the close of business on the record date will constitute a quorum. There must be a quorum for business to be conducted at the special meeting. If a quorum is not present, the presiding officer at the special meeting may adjourn the special meeting from time to time until a quorum is present. Failure of a quorum to be represented at the special meeting will necessitate an adjournment of the special meeting and may subject ProAssurance to additional expense.

If you attend the special meeting or if you submit (and do not thereafter revoke) a proxy by duly executing and returning a proxy card or by telephone or through the internet, even if you abstain from voting, your shares of ProAssurance common stock will be counted for purposes of determining whether a quorum is present at the special meeting. In the event that a quorum is not present at the special meeting or additional votes must be solicited to adopt the merger agreement, the special meeting may be adjourned or postponed to solicit additional proxies.

The approval of the merger proposal requires the affirmative vote of the holders of a majority of the outstanding shares of ProAssurance common stock entitled to vote as of the close of business on the record date.

Assuming a quorum is present, approval of the named executive officer merger-related compensation proposal (on a non-binding basis) requires the affirmative vote of the holders of a majority of the shares of ProAssurance common stock present in person or represented by proxy at the special meeting and entitled to vote thereon.

Assuming a quorum is present, approval of the adjournment proposal requires the affirmative vote of the holders of a majority of the shares of ProAssurance common stock present in person or represented by proxy at the special meeting and entitled to vote thereon.

An abstention occurs when a stockholder attends a meeting, either in person or by proxy, but abstains from voting. At the special meeting, abstentions will be counted as present for purposes of determining whether a quorum is present. Abstaining from voting will have the same effect as a vote “AGAINST” the merger proposal, the named executive officer merger-related compensation proposal or the adjournment proposal.

If no instruction as to how to vote is given (including no instruction to abstain from voting) in an executed, duly returned and not revoked proxy, the proxy will have the same effect as a vote “FOR” the merger proposal, the named executive officer merger-related compensation proposal and the adjournment proposal.

Broker non-votes are shares held in “street name” by brokers, banks and other nominees that are present or represented by proxy at the special meeting, but with respect to which the broker, bank or other nominee is not instructed by the beneficial owner of such shares how to vote on a particular proposal and such broker, bank or other nominee does not have discretionary voting power on such proposal. Because, under NYSE rules, brokers, banks and other nominees holding shares in “street name” do not have discretionary voting authority with respect to any of the three proposals described in this proxy statement, if a beneficial owner of shares of ProAssurance common stock held in “street name” does not give voting instructions to the broker, bank or other nominee, then those shares will not be counted as present in person or by proxy at the special meeting. As the vote to approve the merger proposal is based on the total number of shares of ProAssurance common stock outstanding at the close of business on the record date, not just the shares that are counted as present in person or by proxy at the special meeting, if you fail to issue voting instructions to your broker, bank or other nominee, it will have the same effect as a vote “AGAINST” the merger proposal. If you fail to issue voting instructions to your broker, bank or other nominee, it will have no effect on the outcome of the named executive officer merger-related compensation proposal or the adjournment proposal, assuming a quorum is present.

If you are a stockholder of record and you do not attend the special meeting, sign and return your proxy card by mail or submit your proxy by telephone or over the internet, your shares will not be voted at the special meeting, will not be counted as present in person or by proxy at the special meeting and will not be counted as present for purposes of determining whether a quorum is present.

As discussed above, under the NYSE rules, brokers and other record holders do not have discretionary voting authority with respect to any of the three proposals described in this proxy statement. Accordingly, if you are the beneficial owner of shares held in “street name” and you do not issue voting instructions to your broker, bank or other nominee, your shares will not be voted at the special meeting and will not be counted as present in person or by proxy at the special meeting or counted as present for purposes of determining whether a quorum is present.

A failure to submit a proxy or otherwise attend and vote your shares at the special meeting will have no effect on the outcome of the named executive officer merger-related compensation proposal or the adjournment proposal, in each case, assuming that a quorum is present. The vote to approve the merger proposal, however, is based on the total number of shares of ProAssurance common stock outstanding at the close of business on the record date, not just the shares that are counted as present in person or by proxy at the special meeting. As a result, if you fail to vote your shares, it will have the same effect as a vote “AGAINST” the merger proposal.

If your shares are registered directly in your name with ProAssurance’s transfer agent, you are considered a “stockholder of record.” Stockholders of record can vote their shares of ProAssurance common stock in the following four ways:

Even if you plan to attend the special meeting, you are encouraged to submit a proxy in advance by internet, telephone or mail to ensure that your shares will be represented and voted at the special meeting if you later decide not to attend the special meeting. Telephone and internet facilities for the submission of a proxy to vote shares will be available 24 hours a day and will close at 10:59 p.m., Central Daylight Time on June 23, 2025. Proxy cards must be received no later than June 23, 2025 in order to ensure that your shares are voted.

If your shares are held by your broker, bank or other nominee, you are considered the beneficial owner of shares held in “street name” and you will receive a form from your broker, bank or other nominee seeking instruction from you as to how your shares should be voted. You should instruct your broker, bank or other nominee how to vote your shares on each proposal in accordance with your voting instruction form. If you beneficially own your shares and receive a voting instruction form, you can vote by following the instructions on your voting instruction form. Please refer to information from your bank, broker or other nominee on how to submit voting instructions.

Stockholders who are entitled to vote at the special meeting (and their duly appointed proxies) may attend the special meeting. If you decide to attend the special meeting, please be prepared to provide proper identification, such as a driver’s license. If you hold your shares in “street name” and want to attend the special meeting, you will need to provide proof of ownership, such as a recent account statement or voting instruction form provided a legal proxy from your bank, broker or other nominee, along with proper identification.

You can change or revoke your proxy at any time before the final vote at the special meeting. If you are the stockholder of record, you may change or revoke your proxy by:

If you hold shares in “street name,” you may submit new voting instructions by contacting your bank, broker or other nominee. You may also change your vote at the special meeting, if you attend the special meeting in person.

If you submit a proxy or provide instructions to vote your shares and do not thereafter revoke such proxy or change such instructions in accordance with one of the methods set forth above, your shares will be represented and voted at the special meeting in accordance with your instructions. Attendance at the special meeting will not, in and of itself, result in the revocation of a proxy or cause your shares of ProAssurance common stock to be voted.

The ProAssurance Board is soliciting your proxy, and ProAssurance will bear the cost of soliciting proxies. Okapi Partners LLC has been retained to assist with the solicitation of proxies. Okapi Partners LLC will be paid approximately $25,000, plus certain additional per-service fees, and will be reimbursed for certain fees and expenses for these and other advisory services in connection with the special meeting. Solicitation initially will be made by mail. Forms of proxies and proxy materials may also be distributed through brokers, banks and other nominees to the beneficial owners of shares of ProAssurance common stock, in which case these parties will be reimbursed for their reasonable out-of-pocket expenses. Proxies may also be solicited in person or by telephone, facsimile, electronic mail, or other electronic medium by Okapi Partners LLC or, without additional compensation, by certain of ProAssurance’s directors, officers and employees.

In addition to the merger proposal and the named executive officer merger-related compensation proposal, ProAssurance stockholders are also being asked to approve the adjournment proposal, which will enable the adjournment of the special meeting from time to time, if necessary, as determined in good faith by the

ProAssurance Board, including for the purpose of soliciting additional votes in favor of the merger proposal if there are not sufficient votes at the time of the special meeting to approve the merger proposal. If a quorum is not present, the presiding officer at the special meeting may adjourn the special meeting from time to time until a quorum is present. If the adjournment is for more than 30 days, or if, after the adjournment, a new record date is fixed for the adjourned special meeting, a notice of the adjourned special meeting will be given to each stockholder of record entitled to vote at the special meeting. In addition, the special meeting could be postponed before it commences, subject to the terms of the merger agreement. If the special meeting is adjourned or postponed, stockholders who have already submitted their proxies will be able to revoke them at any time prior to the final vote on the proposals. If you return a proxy and do not indicate how you wish to vote on the adjournment proposal, your shares will be voted in favor of the adjournment proposal.

The ProAssurance Board unanimously recommends a vote “FOR” the adjournment proposal, if necessary, to solicit additional proxies.

You should not send documents representing ProAssurance common stock with the proxy card. If the merger is completed, the paying agent for the merger will send you transmittal materials and instructions for exchanging your shares of ProAssurance common stock for the consideration to be paid to former ProAssurance stockholders in connection with the merger.

If you have more questions about the merger or how to submit your proxy, or if you need additional copies of this proxy statement or the enclosed proxy card or voting instructions, please contact Okapi Partners LLC, ProAssurance’s proxy solicitor, by calling (855) 305-0857 (toll-free) or (212) 297-0720 (banks and brokers).

ProAssurance stockholders are being asked to approve a proposal to adopt the merger agreement, pursuant to which, subject to the terms and conditions set forth therein, and in accordance with the DGCL, Merger Sub will be merged with and into ProAssurance, the separate corporate existence of Merger Sub will thereupon cease, and ProAssurance will survive the merger as a wholly owned subsidiary of The Doctors Company.

The affirmative vote of the holders of a majority of the outstanding shares of ProAssurance common stock entitled to vote as of the close of business on the record date to adopt the merger agreement at the special meeting is a condition to the completion of the merger. If ProAssurance stockholders fail to approve the merger proposal, the merger will not occur.

The ProAssurance Board unanimously recommends that ProAssurance stockholders vote “FOR” the merger proposal.

The discussion of the merger in this proxy statement is qualified in its entirety by reference to the merger agreement, a copy of which is attached to this proxy statement as Annex A and is hereby incorporated by reference into this proxy statement.

Subject to the terms and conditions of the merger agreement and in accordance with the DGCL, if the merger is completed, then at the effective time, Merger Sub will merge with and into ProAssurance, the separate corporate existence of Merger Sub will cease, and ProAssurance will survive the merger as a wholly owned subsidiary of The Doctors Company.

Upon the terms and subject to the conditions of the merger agreement, at the effective time, ProAssurance stockholders will have the right to receive $25.00 in cash, without interest and subject to any applicable withholding taxes, for each share of ProAssurance common stock that they own that is issued and outstanding immediately prior to the effective time of the merger (other than cancelled shares, non-cancelled subsidiary shares and dissenting shares, each as described in the merger agreement). After the merger is completed, ProAssurance stockholders will have only the right to receive a cash payment in respect of their shares of ProAssurance common stock, and will no longer have any rights as ProAssurance stockholders, including voting or other rights.

Any cancelled shares outstanding as of immediately prior to the effective time will be cancelled and retired without any conversion or payment of consideration at the effective time. Any non-cancelled subsidiary shares outstanding as of immediately prior to the effective time will be converted into and become a proportionally equivalent amount of issued, fully paid and non-assessable shares of the surviving corporation.

The merger agreement provides that outstanding ProAssurance equity awards will be treated as set forth below.

Restricted Stock Units. Immediately prior to the effective time, each outstanding unvested ProAssurance RSU will generally, automatically and without any required action on the part of the holder thereof, be immediately vested and be cancelled and will entitle the holder of such ProAssurance RSU to receive, at or promptly after the closing date, an amount in cash, without interest, equal to the product of (a) the total number of shares of ProAssurance common stock subject to the ProAssurance RSU multiplied by (b) $25.00, less applicable tax withholdings.

Performance Shares. Immediately prior to the effective time, each outstanding unvested ProAssurance performance share will, automatically and without any required action on the part of the holder thereof, be immediately vested and be cancelled and will entitle the holder of such ProAssurance performance share to receive, at or promptly after the closing date, an amount in cash, without interest, equal to the product of (a) the total number of shares of ProAssurance common stock subject to the ProAssurance performance share, calculated based on target-level performance multiplied by (b) $25.00, less applicable tax withholdings.

Deferred Shares. Immediately prior to the effective time, all awarded ProAssurance deferred shares will, automatically and without any required action on the part of the holder thereof, be converted into an obligation to pay cash and will entitle the holder of such ProAssurance deferred shares to receive, at or promptly after the closing date, an amount in cash, without interest, equal to the product of (a) the total number of shares of ProAssurance common stock subject to the ProAssurance deferred shares multiplied by (b) $25.00.

Any consideration payable in respect of the ProAssurance RSUs, ProAssurance performance shares and ProAssurance deferred shares will be paid through the payroll system or payroll provider (to the extent applicable) of the surviving corporation as promptly as reasonably practicable following the closing date, but in no event later than seven business days following the closing date. Notwithstanding the foregoing, if any payment owed to a holder of ProAssurance RSUs, ProAssurance performance shares or ProAssurance deferred shares cannot be made through the surviving corporation’s payroll system or payroll provider, then the surviving corporation will issue a wire transfer or direct deposit, or a check for such payment to such holder as promptly as practicable following the closing date but in no event later than five business days thereafter.

Special rules govern the treatment of ProAssurance RSUs that may be granted following the entry into the merger agreement as part of the 2026 long-term incentive award cycle, as further discussed in the section of this proxy statement entitled “The Merger Agreement—Employee Matters” beginning on page 86.

If the merger proposal is not approved by ProAssurance stockholders or if the merger is not completed for any other reason, ProAssurance stockholders will not receive any payment for their shares in connection with the merger. Instead, ProAssurance will remain an independent public company and shares of ProAssurance common stock will continue to be listed and traded on NYSE. In addition, if the merger is not completed, ProAssurance expects that management will operate ProAssurance’s business in a manner similar to that in which it is being operated today and that ProAssurance stockholders will continue to be subject to the same risks and opportunities to which they are currently subject, including, without limitation, risks related to the competitive industry in which ProAssurance operates and adverse economic conditions.

Furthermore, if the merger is not completed, and depending on the circumstances that would have caused the merger not to be completed, it is likely that the price of ProAssurance common stock will decline significantly. If that were to occur, it is uncertain when, if ever, the price of ProAssurance common stock would return to the price at which it trades as of the date of this proxy statement.

Accordingly, if the merger is not completed, there can be no assurance as to the effect of these risks and opportunities on the future value of your shares of ProAssurance common stock. If the merger proposal is not approved by ProAssurance stockholders or if the merger is not completed for any other reason, there can be no assurance that any other transaction acceptable to ProAssurance will be offered or that ProAssurance’s business, prospects or results of operation will not be adversely impacted.

Further, upon termination of the merger agreement, under certain specified circumstances, ProAssurance may be required to pay a termination fee of $52,600,000 to The Doctors Company pursuant to the terms and conditions of the merger agreement. Upon termination of the merger agreement, under certain specified circumstances, The Doctors Company may be required to pay a termination fee of $52,600,000 to ProAssurance pursuant to the terms and conditions of the merger agreement. See the section of this proxy statement entitled “The Merger Agreement—Termination Fees” beginning on page 95 for a discussion of the circumstances under which ProAssurance will be required to pay a termination fee.

The ProAssurance Board and ProAssurance’s management regularly review and assess ProAssurance’s operations and financial performance, industry conditions and related developments as they may impact ProAssurance’s long-term strategic plans and objectives, with the goal of maximizing stockholder value. The ProAssurance Board and ProAssurance’s management regularly evaluate the continued execution of ProAssurance’s strategy as a stand-alone public company and have considered, from time to time, various strategic alternatives.

In furtherance of its consideration of these types of potential strategic alternatives, the ProAssurance Board and ProAssurance’s management have discussed a number of such alternatives with representatives of Goldman

Sachs & Co. LLC (“Goldman Sachs”) from time to time. ProAssurance has periodically consulted with representatives of Goldman Sachs for a number of reasons that include Goldman Sachs’ experience and expertise as a financial advisor in a wide variety of transactions, and Goldman Sachs’ qualifications and experience advising, and familiarity with, companies operating in the insurance industry in particular. In connection with the process that led to the proposed transaction, ProAssurance discussed such matters with representatives of Goldman Sachs throughout the course of the events described below. ProAssurance has also from time to time been advised by Simpson Thacher & Bartlett LLP, ProAssurance’s outside legal counsel (“Simpson Thacher”), in connection with various matters, and ProAssurance worked with representatives of Simpson Thacher throughout the course of the events described below.

On February 28, 2024, Edward L. Rand, Jr., president and chief executive officer of ProAssurance, received an unsolicited call from representatives of Waller Helms Advisors (“Waller Helms”) (subsequently acquired by Houlihan Lokey), financial advisor to The Doctors Company, on behalf of The Doctors Company, to inform Mr. Rand that The Doctors Company was interested in exploring a potential acquisition of ProAssurance. No formal indication of interest was made with respect to such potential acquisition and no valuation was discussed. Mr. Rand informed the ProAssurance Board of this communication.

On March 6, 2024, at the end of a regularly scheduled meeting of the ProAssurance Board, the ProAssurance Board held a session with representatives of ProAssurance management and representatives of Simpson Thacher in attendance. The ProAssurance Board discussed with representatives of management and Simpson Thacher the communication from Waller Helms on behalf of The Doctors Company. Representatives of Simpson Thacher reviewed with the directors their fiduciary duties under applicable law, including in the event a formal indication of interest were to be received from The Doctors Company. The ProAssurance Board discussed engaging a financial advisor in connection with any potential indication of interest that the ProAssurance Board might receive. The ProAssurance Board then appointed Bruce Angiolillo, Samuel Di Piazza and Fabiola Cobarrubias to act as a committee of the ProAssurance Board (which we refer to in this Proxy as the “Transaction Committee”) to oversee the day-to-day process related to any potential indication of interest to acquire ProAssurance and any related potential transaction, subject to the ProAssurance Board retaining control of any material decisions.

On March 11, 2024, representatives of ProAssurance management provided Goldman Sachs with the then-current financial projections for ProAssurance for fiscal years 2024 through 2026 (the “March 2024 Projections”), which had been prepared by ProAssurance management in the ordinary course in connection with the fiscal year end for fiscal year 2023. Thereafter, representatives of ProAssurance management began work to prepare updated financial projections for ProAssurance for fiscal years 2024 through 2028, reflecting certain changes including updates to incorporate observable changes in market conditions.

On March 19, 2024, Dr. Richard Anderson, chief executive officer of The Doctors Company, submitted to Mr. Rand a non-binding written indication of interest (the “Initial Proposal”) to acquire 100% of the common stock of ProAssurance for $20.00 per share of common stock in cash. On the previous trading day, March 18, 2024, the closing price of ProAssurance common stock was $11.86. The Initial Proposal stated The Doctors Company’s belief that the parties would be able to obtain all required regulatory approvals and consents expeditiously and that The Doctors Company had sufficient funds to acquire ProAssurance without any financing contingency. Mr. Rand shared the Initial Proposal with the ProAssurance Board and representatives of Goldman Sachs and Simpson Thacher.

On March 21, 2024, the Transaction Committee met, with ProAssurance senior management, including Mr. Rand, in attendance, to discuss the Initial Proposal and next steps in evaluating such Initial Proposal.

On March 29, 2024, at the direction of the Transaction Committee, representatives of Goldman Sachs met with representatives of Waller Helms to get further clarity on the Initial Proposal, including The Doctors Company’s approach to its valuation of ProAssurance for purposes of the Initial Proposal.

On April 1, 2024, the ProAssurance Board held a meeting with representatives of ProAssurance management, Goldman Sachs and Simpson Thacher in attendance. At the meeting, the ProAssurance Board discussed the Initial Proposal and potential next steps. Representatives of Simpson Thacher reviewed with the directors their fiduciary duties under applicable law. Representatives of ProAssurance management informed the

ProAssurance Board about the preparation of updated financial projections. The ProAssurance Board directed ProAssurance management to continue preparation of the updated financial projections of ProAssurance for discussion with the ProAssurance Board at a future meeting.

On April 15, 2024, the ProAssurance Board held a meeting with representatives of ProAssurance management, Goldman Sachs and Simpson Thacher in attendance. At the meeting, representatives of Goldman Sachs reviewed with the ProAssurance Board Goldman Sachs’ preliminary financial analysis of the Initial Proposal, based on the March 2024 Projections, which had been prepared by ProAssurance management and provided to Goldman Sachs for use in its preliminary financial analysis of the Initial Proposal, it being understood that ProAssurance management was continuing to finalize the updated financial projections. Representatives of Goldman Sachs also discussed with the ProAssurance Board certain potential strategic alternatives, including a comparison of the Initial Proposal to ProAssurance’s standalone plan.

Over the course of the following days, ProAssurance management continued to finalize the financial projections of ProAssurance for fiscal years 2024 through 2028 (as so revised, the “April 2024 Projections”). On April 23, 2024, ProAssurance management provided Goldman Sachs with the April 2024 Projections.

On April 29, 2024, the ProAssurance Board held a meeting with representatives of ProAssurance management, Goldman Sachs and Simpson Thacher in attendance. Prior to the meeting, representatives of Goldman Sachs had provided to the ProAssurance Board, in writing, disclosure of certain relationships between Goldman Sachs and its affiliates and The Doctors Company. At the meeting, representatives of Goldman Sachs reviewed with the ProAssurance Board Goldman Sachs’ preliminary financial analysis of the Initial Proposal based on the April 2024 Projections. Representatives of Simpson Thacher reviewed with the ProAssurance Board certain regulatory considerations. Upon discussion with its advisors and ProAssurance management, the Board concluded that it was not in the best interests of ProAssurance and its stockholders to proceed with discussions with The Doctors Company on the basis of the $20.00 per share valuation reflected in the Initial Proposal. The ProAssurance Board directed representatives of Goldman Sachs to communicate this determination to Waller Helms.

On April 30, 2024, at the direction of the ProAssurance Board, representatives of Goldman Sachs communicated to representatives of Waller Helms that ProAssurance was not willing to proceed with discussions with The Doctors Company on the basis of the $20.00 per share valuation reflected in the Initial Proposal.

On May 9, 2024, Dr. Anderson delivered a letter to Mr. Rand setting forth a revised non-binding written indication of interest with respect to the proposed acquisition by The Doctors Company of ProAssurance for $22.00 per share of common stock in cash (the “May 9 Proposal”). On the previous trading day, May 8, 2024, the closing price of ProAssurance common stock was $14.72. Representatives of Waller Helms communicated to Goldman Sachs that The Doctors Company hoped the May 9 Proposal would be sufficient to facilitate more substantive discussions between the parties, reiterated The Doctors Company’s desire to pursue a transaction with ProAssurance on a friendly basis, and also noted that The Doctors Company had discussed with its advisors potential ways to make its interest public. Mr. Rand shared the May 9 Proposal with the ProAssurance Board.

On May 22, 2024, at the end of a regularly scheduled meeting of the ProAssurance Board, the ProAssurance Board held a session with representatives of ProAssurance management, Goldman Sachs, Simpson Thacher, and Willkie Farr & Gallagher LLP, regulatory counsel to ProAssurance (“Willkie Farr”), in attendance. The ProAssurance Board discussed with ProAssurance’s advisors the May 9 Proposal and certain potential responses to the May 9 Proposal. The ProAssurance Board also discussed the regulatory approval process for a potential transaction and related regulatory risks, with a focus on achieving closing certainty in a potential transaction. Representatives of Goldman Sachs reviewed with the ProAssurance Board Goldman Sachs’ preliminary financial analysis of the May 9 Proposal. Upon discussion with ProAssurance’s advisors, the ProAssurance Board determined that the price offered in the May 9 Proposal did not provide a valuation at which the ProAssurance Board was prepared to fully engage, but that ProAssurance should seek to engage on a limited basis with The Doctors Company, subject to entering into a confidentiality agreement, to provide certain limited financial and related due diligence information that could facilitate a proposal on improved economic terms from The Doctors Company and to better understand regulatory considerations, including perspectives on the allocation of regulatory risk and closing certainty. Representatives of Goldman Sachs communicated this message to representatives of Waller Helms on May 28, 2024.

On May 29, 2024, at the direction of the ProAssurance Board, representatives of Goldman Sachs provided Waller Helms with a draft confidentiality agreement.

On June 7, 2024, the Transaction Committee met, with ProAssurance senior management, including Mr. Rand, in attendance, to discuss the status of the discussions with The Doctors Company and next steps. Following this meeting and over the course of the following months, the Transaction Committee met on a regular basis to oversee the process relating to the events described below.

On June 12, 2024, ProAssurance and The Doctors Company entered into a confidentiality agreement pursuant to which The Doctors Company agreed to certain standstill provisions that fell away upon the announcement of the merger. The standstill provisions expired on March 12, 2025, subject to an exception pursuant to which, beginning on January 6, 2025, The Doctors Company was permitted to make certain public disclosures relating to its interest in the proposed transaction, including descriptions of any proposals made to ProAssurance.

On June 21, 2024, ProAssurance began providing representatives of The Doctors Company and its advisors access to a virtual data room containing certain limited confidential information of ProAssurance, including the April 2024 Projections.

On June 24, 2024, representatives of ProAssurance and The Doctors Company, together with representatives of Goldman Sachs, Simpson Thacher, Willkie Farr and Waller Helms and representatives of Mayer Brown LLP, outside legal counsel to The Doctors Company (“Mayer Brown”), participated in a joint teleconference to discuss certain matters relating to the proposed transaction, including ProAssurance’s focus on the allocation of regulatory risk and the closing certainty presented by the May 9 Proposal.

On July 8, 2024, the Transaction Committee met with other members of the ProAssurance Board, including Mr. Rand, in attendance to discuss the status of the discussions with The Doctors Company, the due diligence process to be conducted by The Doctors Company, and next steps.

On July 18, 2024, ProAssurance and The Doctors Company entered into a further confidentiality agreement (a so-called “clean team” agreement) to facilitate the exchange of certain competitively sensitive information between ProAssurance and The Doctors Company’s independent legal, regulatory and actuarial advisors.

Over the course of July and August 2024, ProAssurance provided certain of The Doctors Company’s independent legal, regulatory, and actuarial advisors access to certain confidential information in a virtual “clean room”. Representatives of Waller Helms and Goldman Sachs held periodic calls to provide updates and coordinate next steps regarding The Doctors Company’s due diligence review process and timing of the proposed transaction.

On August 14, 2024, representatives of Waller Helms contacted representatives of Goldman Sachs to express The Doctors Company’s continued interest in pursuing a potential transaction with ProAssurance and to coordinate next steps regarding The Doctors Company’s proposed due diligence review process and timing of the proposed transaction.

On August 28, 2024, Mr. Rand spoke by phone with Dr. Anderson, to discuss the proposed transaction, including with respect to timing reflected in a proposed timeline that The Doctors Company had delivered to representatives of ProAssurance. Dr. Anderson indicated that The Doctors Company expected to deliver to ProAssurance a further revised indication of interest, based on The Doctors Company’s updated perspectives on valuation and regulatory matters, on or around September 30, 2024. Mr. Rand requested that any such revised indication of interest be delivered on a more accelerated timeline, ahead of a regularly scheduled meeting of the ProAssurance Board on September 11, 2024.

On August 29, 2024 and September 4, 2024, representatives of ProAssurance and representatives of Goldman Sachs participated in calls with representatives of The Doctors Company (only on the September 4, 2024 call) and representatives of Waller Helms to discuss the April 2024 Projections.

On September 9, 2024, representatives of Waller Helms, on behalf of The Doctors Company, delivered to representatives of Goldman Sachs a revised non-binding written indication of interest for The Doctors Company to acquire 100% of the outstanding common stock of ProAssurance for $23.00 in cash per share (the “September 9 Proposal”). On the previous trading day, September 6, 2024, the closing price of ProAssurance common stock was $13.02. The September 9 Proposal included certain proposed terms regarding The Doctors

Company’s regulatory obligations in connection with the proposed transaction, including that (i) The Doctors Company would be obligated to take all actions to obtain the governmental approvals required to consummate the proposed transaction, except that The Doctors Company would not be required to accept regulatory remedies that would have a material adverse effect on either of the parties or on the aggregate financial benefits reasonably expected to be realized by The Doctors Company in connection with the proposed transaction, (ii) The Doctors Company would not be required to accept any rate reduction or rate freeze in any jurisdiction, (iii) The Doctors Company would control the regulatory approval process and strategy, (iv) in the event certain required regulatory approvals were not obtained, The Doctors Company would be obligated to pay to ProAssurance a termination fee equal to 3% of the equity value of the proposed transaction, and (v) ProAssurance would be obligated to pay a regulatory termination fee to The Doctors Company in connection with a failure to obtain certain specified regulatory approvals. Representatives of Goldman Sachs shared the September 9 Proposal with ProAssurance senior management, who subsequently shared the proposal with the ProAssurance Board.

On September 9, 2024, the Transaction Committee met with representatives of ProAssurance management, including Mr. Rand, Goldman Sachs and Simpson Thacher in attendance to discuss the September 9 Proposal and potential next steps.

On September 11, 2024, at the end of a regularly scheduled meeting of the ProAssurance Board, the ProAssurance Board held a session with representatives of ProAssurance management, Goldman Sachs, Simpson Thacher and Willkie Farr in attendance. At the meeting, the ProAssurance Board discussed with ProAssurance management and its advisors the September 9 Proposal. Representatives of Goldman Sachs reviewed with the ProAssurance Board Goldman Sachs’ preliminary financial analysis of the September 9 Proposal based on the April 2024 Projections. Representatives of Simpson Thacher and Willkie Farr reviewed with the ProAssurance Board the terms of the September 9 Proposal, including the proposed allocation of regulatory risk and the termination fee provisions in the September 9 Proposal. The ProAssurance Board also discussed certain risks and potential benefits of engaging with other potentially interested parties. Following discussion, the ProAssurance Board determined that it was not prepared to move forward with The Doctors Company pursuant to the regulatory construct set forth in the September 9 Proposal. The ProAssurance Board instructed its advisors to communicate its determination to The Doctors Company, and to further communicate to The Doctors Company that ProAssurance expected The Doctors Company to agree to (i) accept any regulatory conditions that would not constitute a material adverse effect on either party, and (ii) provide for a regulatory termination fee payable to ProAssurance equal to 6% of the equity value of the proposed transaction if the transaction was terminated as a result of failure to obtain regulatory approvals.

On September 13, 2024, at the direction of the ProAssurance Board, representatives of Goldman Sachs conveyed the determinations of the ProAssurance Board to representatives of Waller Helms and suggested that a call among counsel would be appropriate to further discuss and answer any questions relating to the ProAssurance Board’s views as to the regulatory construct set forth in the September 9 Proposal.

On September 16, 2024, representatives of Simpson Thacher and Willkie Farr had a call with representatives of Mayer Brown to discuss the terms of September 9 Proposal. During this call, representatives of Simpson Thacher conveyed ProAssurance’s position that (i) The Doctors Company would agree to accept any regulatory remedies that would not constitute a material adverse effect on either party, (ii) The Doctors Company would agree to pay a regulatory termination fee to ProAssurance equal to 6% of the equity value of the proposed transaction if the transaction was terminated as a result of failure to obtain regulatory approvals, and (iii) ProAssurance would not be obligated to pay a regulatory termination fee to The Doctors Company under any circumstances.

On September 18, 2024, representatives of Waller Helms informed representatives of Goldman Sachs that The Doctors Company would be submitting a further revised indication of interest with respect to the proposed transaction.

On September 20, 2024, representatives of Waller Helms, on behalf of The Doctors Company, delivered a further revised non-binding written indication of interest (the “September 20 Proposal”) to Goldman Sachs. On the previous trading day, September 19, 2024, the closing price of ProAssurance common stock was $13.50. The material terms (including the proposed valuation and regulatory provisions) were the same as set forth in the September 9 Proposal, except that (i) The Doctors Company would not be obligated to accept regulatory

remedies that would constitute a material adverse effect on either party, (ii) The Doctors Company would not be required to accept any rate freezes or reductions that would, in the aggregate, be material to The Doctors Company and its subsidiaries (including ProAssurance and its subsidiaries), taken as a whole, it being understood that certain specified rate reductions would be material, (iii) the reverse termination fee payable by The Doctors Company in certain circumstances related to a failure of regulatory approvals was increased to 4% of the equity value of the proposed transaction, and (iv) ProAssurance would be required to pay a regulatory termination fee to The Doctors Company equal to 2% of the equity value of the proposed transaction under certain circumstances relating to the failure to obtain regulatory approvals, but which fee would only be payable in connection with a failure to obtain certain specified regulatory approvals. Representatives of Goldman Sachs shared the September 20 Proposal with ProAssurance senior management, who subsequently shared the proposal with the ProAssurance Board.

On September 23, 2024, the Transaction Committee met with representatives of ProAssurance management, including Mr. Rand, Goldman Sachs, Simpson Thacher and Willkie Farr in attendance. The committee reviewed with representatives of ProAssurance management, Goldman Sachs and Simpson Thacher the terms of the September 20 Proposal, the status of The Doctors Company’s due diligence process and certain considerations around timing of the proposed transaction.

Later on September 23, 2024, at the instruction of the Transaction Committee, Mr. Rand and Dr. Anderson held a one-on-one conversation to discuss the proposed transaction and materials terms, including with respect to the allocation of regulatory risk and closing certainty.

On September 30, 2024, Mr. Rand and Dr. Anderson spoke by telephone to continue their discussions regarding the proposed transaction, including the proposed allocation of regulatory risk, closing certainty and other matters.

On October 2, 2024, at the instruction of ProAssurance, representatives of Goldman Sachs conveyed to Waller Helms ProAssurance’s views with respect to the importance of the parties’ respective regulatory efforts, closing certainty and valuation. Representatives of Waller Helms conveyed to representatives of Goldman Sachs that The Doctors Company was not willing to assume a greater share of the regulatory risk in the proposed transaction without a corresponding reduction in valuation. Representatives of Goldman Sachs informed ProAssurance management of this communication.

On October 7, 2024, the Transaction Committee met, with ProAssurance senior management, including Mr. Rand, in attendance, to discuss the September 20 Proposal, material terms of the proposed transaction, and potential responses to The Doctors Company.

On October 9, 2024, representatives of Waller Helms informed representatives of Goldman Sachs that The Doctors Company was not in a position to submit a revised indication of interest without first receiving additional feedback from ProAssurance and its advisors with respect to certain terms.

On October 21, 2024, the Transaction Committee met, with ProAssurance senior management, including Mr. Rand, in attendance, to discuss The Doctors Company’s request for a response on certain key terms of the proposed transaction.

Later on October 21, 2024, at the direction of the Transaction Committee, representatives of Goldman Sachs conveyed to Waller Helms ProAssurance’s position as to (i) the scope of regulatory remedies that The Doctors Company should have to accept, if necessary, in order to achieve required regulatory clearances and (ii) the amount of the regulatory termination fee payable to ProAssurance in certain circumstances if the regulatory clearances are not received, noting that ProAssurance would be willing to accept a termination fee equal to 5% of the equity value of the proposed transaction.

On October 25, 2024, ProAssurance’s and The Doctors Company’s respective internal and external legal counsel participated in a videoconference to further discuss ProAssurance’s October 21, 2024 response.

On November 4, 2024, at the instruction of the Transaction Committee, representatives of Goldman Sachs contacted Waller Helms to discuss next steps with respect to the proposed transaction. Representatives of Waller Helms conveyed that The Doctors Company intended to review ProAssurance’s third quarter earnings release, expected on November 7, 2024, before providing further feedback to ProAssurance. Representatives of Waller Helms also noted that terms related to the allocation of regulatory risk remained open and that The Doctors

Company viewed its valuation of ProAssurance as directly linked to the level of regulatory certainty it could provide in a definitive agreement. As a follow up to this discussion, on November 15, 2024, representatives of Waller Helms communicated to representatives of Goldman Sachs that The Doctors Company was preparing a revised indication of interest, the terms of which would propose to link the merger consideration to the outcome of the regulatory approval process.

On November 18, 2024, the Transaction Committee met, with ProAssurance senior management, including Mr. Rand, in attendance, to discuss the proposed transaction, the recent discussions between ProAssurance’s and The Doctors Company’s respective advisors, and The Doctors Company’s due diligence review process.

On November 27, 2024, representatives of Waller Helms, on behalf of The Doctors Company, delivered to Goldman Sachs a revised non-binding written indication of interest for The Doctors Company to acquire 100% of the outstanding common stock of ProAssurance for $22.00 per share in cash (the “November 27 Proposal”). On the previous trading day, November 26, 2024, the closing price of ProAssurance common stock was $16.50. The November 27 Proposal contemplated the potential increase of the merger consideration to $24.00 in cash per share if, among other things, certain regulatory remedies were not imposed, and to $26.00 in cash per share if no insurance regulator required any decrease in any filed rates for either ProAssurance or The Doctors Company in connection with the regulatory approval process for the proposed transaction. The November 27 Proposal included certain proposed terms regarding The Doctors Company’s regulatory obligations in connection with the proposed transaction, including that (i) The Doctors Company would be obligated to take all actions to obtain the governmental approvals required to consummate the proposed transaction, except that The Doctors Company would not be required to accept regulatory remedies that would have a material adverse effect on either of the parties, (ii) the Doctors Company would control the regulatory approval process and strategy, and (iii) The Doctors Company would be obligated to pay to ProAssurance a termination fee equal to 4% of the equity value of the proposed transaction under certain circumstances relating to the failure to obtain regulatory approvals, but which fee would not be payable in the event certain specified regulatory approvals are not obtained (such exception, the “Reverse Termination Fee Exception”). Representatives of Goldman Sachs shared the November 27 Proposal with ProAssurance senior management, who subsequently shared the proposal with the ProAssurance Board.

On December 3, 2024, the Transaction Committee met with Mr. Rand and representatives of Goldman Sachs in attendance to discuss the November 27 Proposal, with a focus on the variable purchase price contemplated by the proposal. The Transaction Committee discussed the inherent uncertainty in the variable purchase price and expressed concerns that the purchase price was not tied to ProAssurance’s value but rather regulatory outcomes that were beyond ProAssurance’s control and highly uncertain in nature.

During the following weeks, ProAssurance management prepared updated draft financial projections of ProAssurance for fiscal years 2025 through 2029 to reflect certain revised assumptions including to reflect observable changes in market conditions. These projections also included various sensitivity analyses based on different assumptions with respect to the expected outlook relating to macroeconomic conditions and the loss environment.

On December 11, 2024, at the end of a regularly scheduled meeting of the ProAssurance Board, the ProAssurance Board held a session with representatives of ProAssurance management, Goldman Sachs, Simpson Thacher and Willkie Farr in attendance. Representatives of Simpson Thacher reviewed with the ProAssurance Board the process to date with respect to the interactions with The Doctors Company. Representatives of Goldman Sachs reviewed with the ProAssurance Board Goldman Sachs’ preliminary financial analysis of the November 27 Proposal based on the updated draft financial projections. The ProAssurance Board also reviewed with representatives of Goldman Sachs certain counterparties that Goldman Sachs viewed as being the most likely to be interested in a potential acquisition of ProAssurance at this time, and most likely to be able to proceed expeditiously towards a potential transaction, if interested. Representatives of Willkie Farr reviewed with the ProAssurance Board the regulatory approval process and regulatory risks. The ProAssurance Board discussed with its legal and financial advisors and ProAssurance management potential responses to the November 27 Proposal. Upon discussion with its advisors, the ProAssurance Board instructed ProAssurance management to reiterate to The Doctors Company the ProAssurance Board’s focus on closing certainty in connection with a proposed transaction and the ProAssurance Board’s confidence on ProAssurance’s standalone prospects, and to

propose to The Doctors Company that the ProAssurance Board would be willing to have further conversations regarding a potential transaction based on a valuation of $29.00 per share and a regulatory termination fee of 4% of equity value, subject to a “material adverse effect” standard with respect to The Doctors Company’s regulatory efforts.

On December 16, 2024, at the instruction of the ProAssurance Board, Mr. Rand delivered a letter to Dr. Anderson in response to the November 27 Proposal (the “December 16 Response Letter”). The December 16 Response Letter stated that ProAssurance believed the proposed consideration of $22.00 per share reflected in the November 27 Proposal undervalued ProAssurance, that ProAssurance stockholders should not be subject to valuation uncertainty in connection with a proposed transaction by virtue of the regulatory approval process as contemplated in the November 27 Proposal, and that ProAssurance would be willing to negotiate on the basis of a purchase price of $29.00 per share. The December 16 Response Letter further stated that ProAssurance expected The Doctors Company to be obligated to take all necessary actions to obtain regulatory approvals required to complete the transaction, subject only to the limitation The Doctors Company would not be required to agree to any remedy that would result in a material adverse effect on either party, and that, should The Doctors Company accept such terms with respect to regulatory efforts, ProAssurance was willing to accept setting the reverse termination fee at 4% of the equity value of the proposed transaction.

On January 8, 2025, Mr. Rand and Jeffrey Lisenby, ProAssurance’s General Counsel, met in person with Dr. Anderson and Robert White, President of The Doctors Company, in California to discuss the proposed transaction. During the meeting, Mr. Rand reiterated ProAssurance’s concerns with The Doctors Company’s position on the allocation of regulatory risk and reiterated ProAssurance’s focus on closing certainty for any proposed transaction.

On January 17, 2025, Dr. Anderson delivered to Mr. Rand a revised non-binding written indication of interest for The Doctors Company to acquire 100% of the outstanding common stock of ProAssurance for $24.00 in cash per share (the “January 17 Proposal”). On the previous trading day, January 16, 2025, the closing price of ProAssurance common stock was $15.25. As requested by ProAssurance in its December 16 Response Letter, the January 17 Proposal did not condition the proposed merger consideration on the outcome of the regulatory approval process. Additionally, the January 17 Proposal stated that The Doctors Company would be willing to accept ProAssurance’s proposal with respect to the parties’ regulatory efforts, the material adverse effect exception relating thereto and the amount of the regulatory reverse termination fee, as set forth in ProAssurance’s December 16 Response Letter, but expressly noted that the other terms applicable to such termination fee as set forth in the November 27 Proposal would continue to apply, including the Reverse Termination Fee Exception. In his cover note, Dr. Anderson also stated that, while The Doctors Company hoped to continue discussions about the proposed transaction based on the January 17 Proposal, The Doctors Company continued to prepare for alternative approaches at the end of the standstill period under the confidentiality agreement between the parties.

On January 22, 2025, the ProAssurance Board met with representatives of ProAssurance management, Goldman Sachs, Simpson Thacher and Willkie Farr in attendance. At this meeting, the ProAssurance Board reviewed the status of negotiations with The Doctors Company and the proposed transaction, including the terms of the January 17 Proposal. Representatives of Goldman Sachs reviewed with the ProAssurance Board Goldman Sachs’ preliminary financial analysis of the January 17 Proposal based on the Financial Projections. The ProAssurance Board also discussed ProAssurance’s historical and projected financial performance, the overall timeline of the proposed transaction and next steps. With the consent of the ProAssurance Board, the financial projections, referred to herein as the “Financial Projections” and described under “The Merger Proposal (Proposal 1)—Certain Financial Projections” beginning on page 55 of this proxy statement, were provided to Goldman Sachs for its use and reliance in connection with its financial analyses of the proposed transaction. The ProAssurance Board also reviewed with representatives of Goldman Sachs certain counterparties that may be interested in a potential acquisition of ProAssurance at this time, and may be able to proceed expeditiously towards a potential transaction if interested. The ProAssurance Board further discussed with ProAssurance management and its advisors the potential risks and benefits of a potential outreach to certain potential counterparties, including the risk of a leak of the potential transaction with The Doctors Company, the terms of the January 17 Proposal, and the ability of ProAssurance to entertain unsolicited superior proposals following announcement of a transaction with The Doctors Company. The ProAssurance Board determined that it would be in the best interest of ProAssurance and its stockholders to contact certain counterparties in the event that

acceptable terms could be agreed upon with The Doctors Company and prior to finalizing any transaction with The Doctors Company. The ProAssurance Board instructed ProAssurance management to respond to The Doctors Company that the ProAssurance Board believed that a valuation of $26.00 per share would represent an attractive offer for ProAssurance stockholders.

On January 23, 2025, at the direction of the ProAssurance Board, Mr. Rand delivered a letter to Dr. Anderson in response to the January 17 Proposal. The letter conveyed ProAssurance’s position that the proposed merger consideration of $24.00 per share reflected in the January 17 Proposal undervalued ProAssurance, noted that the ProAssurance Board believed that a valuation of $26.00 per share would represent an attractive offer for ProAssurance stockholders and further provided that, if The Doctors Company were to improve its proposal accordingly, ProAssurance would be willing to provide access to an expanded virtual data room and engage in discussion with respect to the negotiation of a definitive agreement for the proposed transaction. Also on January 23, 2025, Mr. Rand and Mr. Lisenby delivered this message in a call with Dr. Anderson and Mr. White.

Later on January 23, 2025, the Transaction Committee met, with ProAssurance senior management, including Mr. Rand, in attendance, to discuss the call between Mr. Rand and Dr. Anderson and next steps.

On January 24, 2025, Dr. Anderson delivered to Mr. Rand a revised non-binding written indication of interest for The Doctors Company to acquire 100% of the outstanding common stock of ProAssurance for $25.00 in cash per share (the “Final Proposal”), noting that this represented The Doctors Company’s “final and best” offer and would be on the terms proposed in the January 17 Proposal. On the previous trading day, January 23, 2025, the closing price of ProAssurance common stock was $14.77.

On January 26, 2025, the ProAssurance Board met with representatives of ProAssurance management, Goldman Sachs and Simpson Thacher in attendance. Upon discussion with ProAssurance management and its legal and financial advisors, the ProAssurance Board determined to direct ProAssurance management to engage with The Doctors Company towards the negotiation of definitive agreements with respect to the proposed transaction based on the Final Proposal. The ProAssurance Board also discussed with representatives of Goldman Sachs the process and strategy with respect to an outreach to certain counterparties that representatives of Goldman Sachs expected to be the most likely to be interested in a potential acquisition of ProAssurance at this time, and most likely to be able to proceed expeditiously towards a potential transaction if interested. The ProAssurance Board directed representatives of Goldman Sachs to reach out to such counterparties to determine their interest in a potential transaction with ProAssurance.

On January 27, 2025 and January 28, 2025, at the direction of the ProAssurance Board, representatives of Goldman Sachs contacted six counterparties to determine their respective interest in a potential acquisition of ProAssurance. Three of such potential acquirors, including a potential financial acquiror referred to herein as “Party A”, executed confidentiality agreements with ProAssurance and received certain confidential information regarding ProAssurance and its business. These confidentiality agreements contained customary standstill provisions, which included “don’t ask, don’t waive” language and which automatically terminated upon the public announcement of the merger. Each of the remaining three potential acquirors informed Goldman Sachs that they were not interested in a potential acquisition of ProAssurance at this time.

On February 7, 2025, at the instruction of ProAssurance, representatives of Simpson Thacher delivered an initial draft of the merger agreement to Mayer Brown.

On February 14, 2025, representatives of Mayer Brown delivered a revised draft of the merger agreement to Simpson Thacher. Thereafter, through the remainder of February and early March, the parties exchanged successive drafts of the merger agreement. ProAssurance, with the assistance of Simpson Thacher, and The Doctors Company with the assistance of Mayer Brown, negotiated various aspects of the transaction, including, among other things, the representations and warranties to be made by the parties, the restriction on the conduct of ProAssurance’s business until completion of the transaction, The Doctors Company’s obligations to obtain regulatory approvals, including regulatory standstill restrictions on The Doctors Company, the conditions to consummation of the transaction, the provisions governing ProAssurance’s ability to participate in discussions and negotiations with third parties relating to unsolicited proposals in certain cases, the right of the ProAssurance Board to change its recommendation that stockholders approve the merger in certain cases, including in response to a superior proposal, the termination provisions and the circumstances in which the respective termination fees would be payable by ProAssurance and The Doctor’s Company, respectively, the ability of each party to seek

damages beyond the applicable termination fee in certain circumstances, provisions regarding the ProAssurance’s equity awards, employee benefit plans, severance and other compensation matters, and that the Reverse Termination Fee Exception would not apply to any termination fee payable by The Doctors Company to ProAssurance under the terms of the merger agreement.

On February 18, 2025, Party A submitted a non-binding written indication of interest to acquire 100% of the common stock of ProAssurance at a price that was below the Final Proposal. Party A’s offer also included an alternative proposal to acquire 9.9% of the outstanding capital stock of ProAssurance and enter into certain commercial arrangements with ProAssurance. None of the other five counterparties that representatives of Goldman Sachs had contacted provided a formal indication of interest.

On February 21, 2025, the ProAssurance Board met with representatives of ProAssurance management, Goldman Sachs, Simpson Thacher and Willkie Farr in attendance. Representatives of Goldman Sachs reviewed with the ProAssurance Board the results of the outreach to the six potential counterparties, including the proposal received from Party A. Upon discussion with ProAssurance management and its legal and financial advisors, the ProAssurance Board determined that it was not in the best interest of ProAssurance and its stockholders to further engage with such counterparties, including Party A. Representatives of Simpson Thacher discussed with the ProAssurance Board certain terms of the proposed merger agreement.

Also on February 21, 2025, ProAssurance and The Doctors Company agreed to amend the terms of the standstill provisions in the confidentiality agreement entered into between the parties in order to facilitate continued discussions. The amendment, among other things, extended the prohibition on public disclosure by The Doctors Company of its interest in a potential transaction with ProAssurance (which prohibition had previously expired on January 6, 2025). The standstill provisions fell away automatically upon the announcement of the merger agreement.

On February 27, 2025, representatives of Goldman Sachs contacted Party A and indicated that the purchase price in Party A’s bid was lower than a value at which ProAssurance was willing to engage. Following the delivery of such message, Party A did not deliver to ProAssurance or Goldman Sachs a revised indication of interest, or otherwise propose revised terms, with respect to a potential transaction involving ProAssurance.

Throughout late February 2025 and early March 2025, The Doctors Company and its representatives continued to conduct confirmatory due diligence on ProAssurance and its business. During this period, representatives of ProAssurance participated in a series of due diligence sessions with representatives of The Doctors Company, including on financial, actuarial, regulatory, legal and operational matters.

On March 5, 2025, during a regularly scheduled meeting of the ProAssurance Board, the ProAssurance Board held a session with representatives of ProAssurance management, Goldman Sachs, Simpson Thacher and Willkie Farr in attendance. Representatives of Goldman Sachs discussed with the ProAssurance Board the status of The Doctors Company’s due diligence process, and recent discussions among the parties’ respective legal and financial advisors with respect to timing of a potential announcement of the proposed transaction. Representatives of Simpson Thacher discussed with the ProAssurance Board the terms of the draft merger agreement. Representatives of Willkie Farr discussed with the ProAssurance Board certain regulatory matters. The ProAssurance Board discussed with ProAssurance management certain matters relating to communications with stockholders, employees and other constituencies following announcement of a transaction.

On March 11, 2025, Simpson Thacher delivered to Mayer Brown an initial draft of ProAssurance’s disclosure letter to the merger agreement. Thereafter and until the date of the merger agreement, the parties exchanged successive drafts of the ProAssurance disclosure letter.

On March 15, 2025, representatives of ProAssurance, The Doctors Company and their respective legal counsel held a meeting to discuss the remaining open terms of the merger agreement. During this meeting, the parties discussed and substantially aligned on material terms, including with respect to the circumstances in which the respective termination fees would be payable, the amount of each party’s termination fee, the provisions relating to control over the regulatory approval process, certain regulatory standstill restrictions on The Doctors Company’s obligations, and the ability of each party to seek remedies beyond the applicable termination fee in certain circumstances. Thereafter, between March 15, 2025 and March 19, 2025, representatives of Simpson Thacher and Mayer Brown discussed, negotiated and finalized the terms of the merger agreement and the disclosure letter.

On March 18, 2025, the ProAssurance Board met with representatives of ProAssurance management, Goldman Sachs, Simpson Thacher and Willkie Farr in attendance. At the meeting, representatives of Goldman Sachs and ProAssurance’s legal advisors updated the ProAssurance Board with respect to the developments over the past several days. Representatives of Simpson Thacher reviewed with the ProAssurance Board the directors’ fiduciary duties under applicable law and the terms of the draft merger agreement. Representatives of Goldman Sachs reviewed with the ProAssurance Board Goldman Sachs’ preliminary financial analysis of the proposed transaction. The ProAssurance Board considered the terms of the proposed transaction and the risks and potential benefits of a potential transaction as compared to ProAssurance’s long-term strategic plan as an independent public company and the risks associated with executing such plan. Representatives of ProAssurance management reviewed with the ProAssurance Board certain matters relating to communications with various constituencies following announcement of a transaction.

On March 19, 2025, the ProAssurance Board held a meeting with representatives of ProAssurance management, Goldman Sachs, Simpson Thacher and Willkie Farr in attendance. Prior to the meeting, representatives of Goldman Sachs had provided to the ProAssurance Board, in writing, disclosure of certain relationships between Goldman Sachs and its affiliates and The Doctors Company. At the meeting, representatives of Simpson Thacher reviewed with the ProAssurance Board the directors’ fiduciary duties under applicable law and the terms of the final merger agreement. Representatives of Goldman Sachs reviewed with the ProAssurance Board Goldman Sachs’ financial analysis of the potential transaction based upon the Financial Projections provided to Goldman Sachs, with the consent of the ProAssurance Board, for Goldman Sachs’ use and reliance. Goldman Sachs rendered an oral opinion to the ProAssurance Board (which was subsequently confirmed by delivery of Goldman Sach’s written opinion dated as March 19, 2025), that, as of the date of the opinion, and based upon and subject to the assumptions, limitations, qualifications and conditions described in Goldman Sachs’ opinion, it was Goldman Sachs’ opinion that, the $25.00 in cash per share of ProAssurance common stock to be paid to the holders of shares of ProAssurance common stock (other than The Doctors Company and its affiliates) pursuant to the merger agreement was fair from a financial point of view to such holders. The written opinion is attached to this proxy statement as Annex B. The ProAssurance Board considered that, aside from their interests as ProAssurance stockholders, ProAssurance’s directors and executive officers have interests in the merger that may be different from, or in addition to, the interests of other ProAssurance stockholders generally, as described in more detail in “The Merger Proposal (Proposal 1)—Interests of ProAssurance’s Executive Officers and Directors in the Merger” beginning on page 57 of this proxy statement. After further discussion and deliberation, the ProAssurance Board unanimously (i) approved and declared advisable the merger agreement and the transactions contemplated thereby, including the merger, (ii) determined that the merger agreement and the transactions contemplated thereby, including the merger, are in the best interests of ProAssurance and the ProAssurance stockholders, (iii) directed that the merger agreement be submitted to the ProAssurance stockholders for adoption and (iv) recommended that the merger agreement be adopted by the ProAssurance stockholders.

Following the meeting of the ProAssurance Board, at the direction of the ProAssurance Board, representatives of Simpson Thacher notified representatives of The Doctors’ Company and Mayer Brown that the ProAssurance Board had adopted resolutions approving the transaction. Promptly thereafter, ProAssurance and The Doctors Company both executed the merger agreement and announced the execution of the merger agreement.

The ProAssurance Board recommends that you vote “FOR” the merger proposal.

At a meeting of the ProAssurance Board held on March 19, 2025, the ProAssurance Board, acting in consultation with its outside legal counsel and financial advisors, unanimously (a) approved and declared advisable the merger agreement and the transactions contemplated thereby, including the merger, (b) determined that the merger agreement and the transactions contemplated thereby, including the merger, are in the best interests of ProAssurance and the ProAssurance stockholders, (c) directed that the merger agreement be submitted to the ProAssurance stockholders for adoption and (d) recommended that the merger agreement be adopted by the ProAssurance stockholders.

When you consider the ProAssurance Board’s recommendation, you should be aware that ProAssurance’s directors may have interests in the merger that may be different from, or in addition to, the interests of

ProAssurance stockholders generally. These interests are described in the section entitled “The Merger Proposal (Proposal 1)—Interests of ProAssurance’s Executive Officers and Directors in the Merger”.

Factors the ProAssurance Board Considered Supporting the Approval of the Merger

In the course of reaching its decision, the ProAssurance Board consulted with ProAssurance’s management and financial and legal advisors, reviewed a significant amount of information and considered a number of potentially positive factors that it believed supported its decision, including, among others, the following (not necessarily in order of relative importance):

Other Factors Considered by the ProAssurance Board.

In the course of reaching its decision, the ProAssurance Board also considered and balanced against the potential benefits of the merger a number of potentially adverse factors with respect to the merger and the other transactions contemplated by the merger agreement including, among others, the following (not necessarily in the order of relative importance):

While the ProAssurance Board considered potentially positive and potentially negative factors, the ProAssurance Board concluded that, overall, the potentially positive factors outweighed the potentially negative factors. Accordingly, the ProAssurance Board unanimously determined that the merger agreement and the transactions contemplated thereby, including the merger, are advisable and in the best interests of ProAssurance and its stockholders.

The foregoing discussion is not intended to be an exhaustive list of the information and factors considered by the ProAssurance Board in its consideration of the merger, but includes the material positive factors and material negative factors considered by the ProAssurance Board in that regard. In view of the number and variety of factors, the ProAssurance Board did not find it practicable to, nor did it attempt to, make specific assessments of, quantify, or otherwise assign relative weights to, the specific factors considered in reaching its determination. In addition, individual members of the ProAssurance Board may have given different weights to different factors. Based on the totality of the information presented, the ProAssurance Board collectively reached the unanimous decision to authorize and approve the execution, delivery and performance of the merger agreement and the transactions contemplated thereby, including the merger, in light of the factors described above and other factors that the members of the ProAssurance Board felt were appropriate.

Portions of this explanation of ProAssurance’s reasons for the merger and other information presented in this section are forward-looking in nature and, therefore, should be read in light of the section entitled “Cautionary Statement Regarding Forward-Looking Statements”, beginning on page 26 of this proxy statement.

Goldman Sachs rendered its oral opinion to the ProAssurance Board (which was subsequently confirmed by delivery of Goldman Sachs’ written opinion dated as of March 19, 2025) that, as of March 19, 2025 and based upon and subject to the factors and assumptions set forth therein, the $25.00 in cash per share of ProAssurance common stock to be paid to the holders of ProAssurance common stock (other than The Doctors Company and its affiliates) pursuant to the merger agreement was fair from a financial point of view to such holders of ProAssurance common stock.

The full text of the written opinion of Goldman Sachs, dated March 19, 2025, which sets forth the assumptions made, procedures followed, matters considered and limitations on the review undertaken in connection with the opinion, is attached as Annex B. Goldman Sachs provided advisory services and its opinion for the information and assistance of the ProAssurance Board in connection with its consideration of the merger. Goldman Sachs’ opinion is not a recommendation as to how any holder of ProAssurance common stock should vote with respect to the merger, or any other matter.

In connection with rendering the opinion described above and performing its related financial analyses, Goldman Sachs reviewed, among other things:

Goldman Sachs also held discussions with members of the senior management of ProAssurance regarding their assessment of the past and current business operations, financial condition and future prospects of ProAssurance; reviewed the reported price and trading activity for the ProAssurance common stock; compared certain financial and stock market information for ProAssurance with similar information for certain other companies the securities of which are publicly traded; reviewed the financial terms of certain recent business combinations in the insurance industry and in other industries; and performed such other studies and analyses, and considered such other factors, as it deemed appropriate.

For purposes of rendering this opinion, Goldman Sachs, with ProAssurance’s consent, relied upon and assumed the accuracy and completeness of all of the financial, legal, regulatory, tax, accounting and other information provided to, discussed with or reviewed by, it, without assuming any responsibility for independent verification thereof. In that regard, Goldman Sachs assumed with ProAssurance’s consent that the Financial Projections were reasonably prepared on a basis reflecting the best currently available estimates and judgments of the management of ProAssurance. Goldman Sachs did not make an independent evaluation or appraisal of the assets and liabilities (including any contingent, derivative or other off-balance-sheet assets and liabilities) of ProAssurance or any of its subsidiaries and it was not furnished with any such evaluation or appraisal. Goldman Sachs is not an actuary and its services did not include any actuarial determination or evaluation by it or any attempt to evaluate actuarial assumptions and it relied on ProAssurance’s actuaries with respect to reserve adequacy. In that regard, Goldman Sachs made no analysis of, and expressed no opinion as to, the adequacy of the policy liabilities and accruals of ProAssurance. Goldman Sachs assumed that all governmental, regulatory or other consents and approvals necessary for the consummation of the merger will be obtained without any adverse effect on the expected benefits of the merger in any way meaningful to its analysis. Goldman Sachs also assumed that the merger will be consummated on the terms set forth in the merger agreement, without the waiver or modification of any term or condition the effect of which would be in any way meaningful to its analysis.

Goldman Sachs’ opinion does not address the underlying business decision of ProAssurance to engage in the transaction, or the relative merits of the transaction as compared to any strategic alternatives that may be available to ProAssurance; nor does it address any legal, regulatory, tax or accounting matters. Goldman Sachs’ opinion addresses only the fairness from a financial point of view to the holders (other than The Doctors Company and its affiliates) of ProAssurance common stock, as of the date of the opinion, of the $25.00 in cash per share of ProAssurance common stock to be paid to such holders pursuant to the merger agreement. Goldman Sachs does not express any view on, and its opinion does not address, any other term or aspect of the merger agreement or the transaction or any term or aspect of any other agreement or instrument contemplated by the merger agreement or entered into or amended in connection with the merger, including, the fairness of the merger to, or any consideration received in connection therewith by, the holders of any other class of securities, creditors, or other constituencies of ProAssurance; nor as to the fairness of the amount or nature of any compensation to be paid or payable to any of the officers, directors or employees of ProAssurance, or class of such persons in connection with the transaction, whether relative to the $25.00 in cash per share of ProAssurance common stock to be paid to holders (other than The Doctors Company and its affiliates) of ProAssurance common stock pursuant to the merger agreement or otherwise. Goldman Sachs’ opinion is necessarily based on economic, monetary, market and other conditions as in effect on, and the information made available to Goldman Sachs as of, the date of its opinion and Goldman Sachs assumes no responsibility for updating, revising or reaffirming its opinion based on circumstances, developments or events occurring after the date of its opinion. In

addition, Goldman Sachs does not express any opinion as to the prices at which shares of ProAssurance common stock will trade at any time, or as to the potential effects of volatility in the credit, financial and stock markets on ProAssurance, The Doctors Company, or the merger, or as to the impact of the merger on the solvency or viability of ProAssurance or The Doctors Company or the ability of ProAssurance or The Doctors Company to pay their respective obligations when they come due. Goldman Sachs’ opinion was approved by a fairness committee of Goldman Sachs.

The following is a summary of the material financial analyses delivered by Goldman Sachs to the ProAssurance Board in connection with rendering the opinion described above. The following summary, however, does not purport to be a complete description of the financial analyses performed by Goldman Sachs, nor does the order of analyses described represent relative importance or weight given to those analyses by Goldman Sachs. Some of the summaries of the financial analyses include information presented in tabular format. The tables must be read together with the full text of each summary and are alone not a complete description of Goldman Sachs’ financial analyses. Except as otherwise noted, the following quantitative information, to the extent that it is based on market data, is based on market data as it existed on or before March 18, 2025, the last trading day before the public announcement of the merger, and is not necessarily indicative of current market conditions.

Analysis of Implied Premiums. Goldman Sachs analyzed the $25.00 in cash per share of ProAssurance common stock to be paid to holders of ProAssurance common stock pursuant to the merger agreement in relation to:

This analysis indicated that the price per share to be paid to ProAssurance stockholders pursuant to the merger agreement represented:

Illustrative Dividend Discount Analysis. Using the Financial Projections, Goldman Sachs performed an illustrative dividend discount analysis on ProAssurance to derive a range of illustrative present values per share of ProAssurance common stock. Using the mid-year convention for discounting dividends and discount rates ranging from 7.50% to 9.00%, reflecting estimates of ProAssurance’s cost of equity, Goldman Sachs discounted to present value, as of December 31, 2024, (x) capital return to holders of ProAssurance common stock (in the form of dividends paid to holders of ProAssurance common stock) for the calendar years 2025 through 2029, as reflected in the Financial Projections, and (y) a range of terminal values for ProAssurance calculated by applying terminal year exit price to Book Value including the accumulated other comprehensive income (which we refer to as the “AOCI”) multiples ranging from 0.65x to 1.15x to a terminal year estimate of the Book Value (incl. AOCI) of ProAssurance, as reflected in the Financial Projections. The range of terminal year exit price to Book Value (incl. AOCI) multiples was estimated by Goldman Sachs utilizing its professional judgment and experience, taking into account current and historical price to Book Value (incl. AOCI) multiples of ProAssurance. Goldman Sachs derived such discount rates reflecting estimates of ProAssurance’s cost of equity by application of the Capital Asset Pricing Model (“CAPM”), which requires certain company-specific inputs, including a beta for the company, as well as certain financial metrics for the United States financial markets generally. Goldman Sachs then divided the range of illustrative equity values it derived by the total number of ProAssurance standalone diluted shares outstanding. This analysis implied a value of $16.81 to $28.93 per share of ProAssurance common stock as of December 31, 2024 (based on the total number of ProAssurance standalone diluted shares outstanding as of March 18, 2025, which was comprised of ProAssurance common stock, ProAssurance RSUs and ProAssurance PSUs, as provided by ProAssurance’s management and approved for use by Goldman Sachs (the “ProAssurance standalone diluted shares outstanding”)).

Illustrative Present Value of Future Share Price Analysis. Using the Financial Projections, Goldman Sachs performed an illustrative analysis of the implied present value of an illustrative future value per share of ProAssurance common stock. For this analysis, Goldman Sachs first calculated and implied a range of theoretical future values per share of ProAssurance common stock as of December 31 for each of the fiscal years 2025 through 2027, by applying a range of multiples of illustrative price to Book Value (incl. AOCI) of 0.50x to 1.00x to estimates of ProAssurance’s projected Book Value (incl. AOCI) per share of ProAssurance common stock for each of the fiscal years 2025 through 2027 (based on the total number of ProAssurance standalone diluted shares outstanding as of December 31 of each year per the Financial Projections). This range of illustrative price to Book Value (incl. AOCI) multiples was derived by Goldman Sachs utilizing its professional judgment and experience, taking into account current and historical price to Book Value (incl. AOCI) multiples of ProAssurance.

Goldman Sachs then added the cumulative dividends per share of ProAssurance common stock expected to be paid to holders of shares of ProAssurance common stock through the end of each of fiscal years 2025 through 2027, using the Financial Projections. Goldman Sachs then discounted these implied future equity values per share of ProAssurance common stock to December 31, 2024, using an illustrative discount rate of 8.25%, reflecting the midpoint of Goldman Sachs’ range of estimates of ProAssurance’s cost of equity. Goldman Sachs derived such discount rate by application of CAPM, which requires certain company-specific inputs, including a beta for the company, as well as certain financial metrics for the United States financial markets generally. This analysis resulted in a range of implied present values of $11.57 to $23.38 per share of ProAssurance common stock.

Selected Transactions Analysis. Goldman Sachs analyzed certain information relating to the following selected transactions in the property and casualty insurance industry since 2015. For each of the selected transactions, Goldman Sachs calculated and compared the implied equity value of the applicable target company based on the consideration paid in the transaction as a multiple of the target company’s book value (including AOCI) (a “P/BV (incl. AOCI) multiple”) based on information in public filings, press releases and investor

relations documents. While none of the companies that participated in the selected transactions are directly comparable to ProAssurance, the companies that participated in the selected transactions are companies with operations that, for the purposes of analysis, may be considered similar to certain of ProAssurance’s results, market sizes and product profile.

The following table presents the results of this analysis:

Based on the results of the foregoing calculations and Goldman Sachs’ professional judgment and experience, Goldman Sachs applied a reference range of P/BV (incl. AOCI) multiples of 0.90x to 1.74x (representing the low and high, respectively, of the implied P/BV (incl. AOCI) multiples calculated for the transactions above) to ProAssurance’s Book Value (incl. AOCI) of $1.202 billion as of December 31, 2024, as provided by and approved for Goldman Sachs’ use by the management of ProAssurance, and based on the total number of ProAssurance standalone diluted shares outstanding as of March 18, 2025 to derive a reference range of implied values per share of ProAssurance common stock of $21.04 to $40.78.

Premia Paid Analysis. Goldman Sachs reviewed and analyzed, using publicly available information, the acquisition premia for all-cash acquisition transactions announced from 2015 through March 18, 2025 involving a public company based in the United States as the target where the disclosed equity values for the transaction were greater than $500 million. For the entire period, using publicly available information, Goldman Sachs calculated the median, 25th percentile and 75th percentile premiums of the price paid relative to the target’s closing stock price one day prior to announcement of the respective transaction. This analysis indicated a median premium of 22.6% across the period. This analysis also indicated a 25th percentile premium of 8.2% and 75th percentile premium of 45.7% across the period. Using this analysis, Goldman Sachs applied a reference range of illustrative premiums of 8.2% to 45.7% to the closing price per share of ProAssurance common stock of $15.74 as of March 18, 2025 and calculated a range of implied equity values per share of ProAssurance common stock of $17.03 to $22.93.

The preparation of a fairness opinion is a complex process and is not necessarily susceptible to partial analysis or summary description. Selecting portions of the analyses or of the summary set forth above, without considering the analyses as a whole, could create an incomplete view of the processes underlying Goldman Sachs’ opinion. In arriving at its fairness determination, Goldman Sachs considered the results of all of its analyses and did not attribute any particular weight to any factor or analysis considered by it. Rather, Goldman Sachs made its determination as to fairness on the basis of its experience and professional judgment after considering the results of all of its analyses. No company or transaction used in the above analyses as a comparison is directly comparable to ProAssurance or The Doctors Company or the merger.

Goldman Sachs prepared these analyses for purposes of Goldman Sachs’ providing its opinion to the ProAssurance Board as to the fairness from a financial point of view to the holders (other than The Doctors Company and its affiliates) of the shares of ProAssurance common stock of the $25.00 in cash per share of ProAssurance common stock to be paid to such holders pursuant to the merger agreement. These analyses do not purport to be appraisals nor do they necessarily reflect the prices at which businesses or securities actually may be sold. Analyses based upon forecasts of future results are not necessarily indicative of actual future results, which may be significantly more or less favorable than suggested by these analyses. Because these analyses are inherently subject to uncertainty, being based upon numerous factors or events beyond the control of the parties or their respective advisors, none of ProAssurance, The Doctors Company, Goldman Sachs or any other person assumes responsibility if future results are materially different from those forecast.

The $25.00 in cash per share of ProAssurance common stock was determined through arm’s-length negotiations between ProAssurance and The Doctors Company and was approved by the ProAssurance Board. Goldman Sachs provided advice to ProAssurance during these negotiations. Goldman Sachs did not, however, recommend any specific amount of consideration to ProAssurance or the ProAssurance Board or that any specific amount of consideration constituted the only appropriate consideration for the merger.

As described above, Goldman Sachs’ opinion to the ProAssurance Board was one of many factors taken into consideration by the ProAssurance Board in making its determination to approve the merger agreement. The foregoing summary does not purport to be a complete description of the analyses performed by Goldman Sachs in connection with the fairness opinion and is qualified in its entirety by reference to the written opinion of Goldman Sachs attached as Annex B.

Goldman Sachs and its affiliates are engaged in advisory, underwriting, lending and financing, principal investing, sales and trading, research, investment management and other financial and non-financial activities and services for various persons and entities. Goldman Sachs and its affiliates and employees, and funds or other entities they manage or in which they invest or have other economic interests or with which they co-invest, may at any time purchase, sell, hold or vote long or short positions and investments in securities, derivatives, loans, commodities, currencies, credit default swaps and other financial instruments of ProAssurance, The Doctors Company, any of their respective affiliates and third parties, and any of their respective affiliates or any currency or commodity that may be involved in the transaction contemplated by the merger agreement. Goldman Sachs acted as financial advisor to ProAssurance in connection with, and participated in certain of the negotiations leading to, the transaction contemplated by the merger agreement. During the two-year period ended March 19, 2025, Goldman Sachs Investment Banking has not been engaged by ProAssurance or The Doctors Company or any of its/their respective affiliates to provide financial advisory or underwriting services for which Goldman Sachs has recognized compensation. Goldman Sachs may also in the future provide financial advisory and/or underwriting services to ProAssurance, The Doctors Company and their respective affiliates for which Goldman Sachs Investment Banking may receive compensation.

The ProAssurance Board selected Goldman Sachs as its financial advisor because it is an internationally recognized investment banking firm that has substantial experience in transactions similar to the merger. Pursuant to a letter agreement dated September 18, 2024, as supplemented by a letter agreement dated March 10, 2025, ProAssurance engaged Goldman Sachs to act as its financial advisor in connection with the contemplated transaction. The engagement letter, as supplemented, between ProAssurance and Goldman Sachs provides for a transaction fee that is estimated, based on the information available as of the date of announcement, at approximately $26 million, $5 million of which became payable at announcement of the merger, and the remainder of which is contingent upon consummation of the merger. In addition, ProAssurance has agreed to reimburse Goldman Sachs for certain of its expenses, including attorneys’ fees and disbursements, and to indemnify Goldman Sachs and related persons against various liabilities, including certain liabilities under the federal securities laws.

ProAssurance does not, as a matter of course, publicly disclose projections as to its future financial results. ProAssurance senior management prepared and provided to the ProAssurance Board at its meeting on January 22, 2025, certain non-public financial forecasts based on management’s reasonable best estimates, judgments and assumptions with respect to ProAssurance’s future financial performance at the time such forecasts were prepared, as further described in the section of this proxy statement entitled “The Merger

Proposal (Proposal 1)—Background of the Merger,” beginning on page 34 of this proxy statement, and which we refer to as the “Financial Projections”. With the consent of the ProAssurance Board, the Financial Projections were provided to Goldman Sachs for its use and reliance in connection with its financial analyses summarized above under “The Merger Proposal (Proposal 1)—Opinion of ProAssurance’s Financial Advisor”, beginning on page 50 of this proxy statement. Goldman Sachs expressed no view or opinion as to these financial projections or the assumptions on which they were based. A summary of the Financial Projections is set forth below:

The Financial Projections were not prepared with a view to public disclosure or with a view toward compliance with SEC rules and are included in this proxy statement only because, with the consent of the ProAssurance Board, the Financial Projections were provided to Goldman Sachs for its use and reliance in connection with its financial analyses summarized above under “The Merger Proposal (Proposal 1)—Opinion of ProAssurance’s Financial Advisor.” The Financial Projections were not prepared with a view to compliance with generally accepted accounting principles as applied in the United States (“GAAP”), the published guidelines of the SEC regarding projections and forward-looking statements or the guidelines established by the American Institute of Certified Public Accountants for preparation and presentation of prospective financial information. The Financial Projections were prepared by, and are the responsibility of, ProAssurance’s management. Ernst & Young LLP (“E&Y”) has not audited, reviewed, examined, compiled nor applied agreed-upon procedures with respect to the Financial Projections and, accordingly, E&Y does not express an opinion or any other form of assurance with respect thereto. The E&Y report incorporated by reference in this proxy statement relates to ProAssurance’s previously issued financial statements. It does not extend to the Financial Projections and should not be read to do so. The Financial Projections were prepared solely for internal use of ProAssurance and are subjective in many respects. ProAssurance has made no representations to The Doctors Company or Merger Sub, in the merger agreement or otherwise, concerning any projected financial information, including the Financial Projections.

The Financial Projections are forward-looking statements. Although this summary of the Financial Projections is presented with numerical specificity, the Financial Projections reflect numerous variables, assumptions and estimates as to future events made by ProAssurance’s management that it believed were reasonable at the time the Financial Projections were prepared, taking into account the relevant information available to management at the time and presented as of the time of the preparation, to the best of management’s knowledge and belief, the expected course of action and the expected future financial performance of ProAssurance on a stand-alone basis as described above and subject to certain assumptions and limitations. Such variables, assumptions and estimates are inherently uncertain and many of which are beyond the control of ProAssurance’s management. Although ProAssurance’s management believes there is a reasonable basis for the

Financial Projections, ProAssurance cautions shareholders that future results could be materially different from the Financial Projections. Because the Financial Projections cover multiple years, by their nature, they become less predictive with each successive year. This information is not fact and should not be relied upon as being necessarily indicative of actual future results. The Financial Projections are subject to estimates and assumptions in many respects and, as a result, subject to interpretation. These estimates and assumptions may prove inaccurate for any number of reasons, including general economic conditions, competition and other risks. For information on factors that may cause ProAssurance’s future results to materially vary, see the section of this proxy statement entitled “Cautionary Statement Regarding Forward-Looking Statements”, beginning on page 26 of this proxy statement.

In addition, the Financial Projections do not take into account any circumstances or events occurring after the date that they were prepared and do not give effect to the merger. Because the Financial Projections were developed on a stand-alone basis without giving effect to the merger, they do not reflect any divestitures or other restrictions that may be imposed in connection with the receipt of any necessary governmental or regulatory approvals, any synergies realized as a result of the merger or any changes to ProAssurance’s operations or strategy that may be implemented after completion of the merger. As a result, there can be no assurance that the Financial Projections will be realized, and actual results may be materially better or worse than those contained in the Financial Projections. The inclusion of this information should not be regarded as an indication that the ProAssurance Board, ProAssurance, Goldman Sachs, The Doctors Company, Merger Sub, and their respective representatives or affiliates or any other recipient of this information considered, or now considers, the Financial Projections to be necessarily predictive of actual future results. The summary of the Financial Projections is not included in this proxy statement in order to induce any stockholder to vote in favor of the merger proposal or any of the other proposals to be voted on at the special meeting.

Except to the extent required by applicable federal securities laws, ProAssurance does not intend, and expressly disclaims any responsibility, to update or otherwise revise the Financial Projections to reflect circumstances existing after the date when ProAssurance prepared the Financial Projections or to reflect the occurrence of future events or changes in general economic or industry conditions, even in the event that any of the assumptions underlying the Financial Projections are shown to be in error. By including in this document a summary of certain financial projections, neither ProAssurance nor any of its representatives or advisors (including Goldman Sachs) nor The Doctors Company or its representatives or affiliates makes any representation to any person regarding the ultimate performance of ProAssurance or the surviving corporation compared to the information contained in such financial forecasts and should not be read to do so.

Certain of the measures included in the Financial Projections may be considered non-GAAP financial measures. Non-GAAP financial measures should not be considered in isolation from, or as a substitute for, financial information presented in compliance with GAAP, and non-GAAP financial measures as used by ProAssurance may not be comparable to similarly titled amounts used by other companies. With the consent of the ProAssurance Board, the non-GAAP financial measures were relied upon by Goldman Sachs in connection with its financial analyses summarized above under “The Merger Proposal (Proposal 1)—Opinion of ProAssurance’s Financial Advisor”, beginning on page 50 of this proxy statement, and by the ProAssurance Board in connection with its consideration of the merger. Financial measures provided to a financial advisor in connection with a business combination transaction are excluded from the definition of non-GAAP financial measures and therefore are not subject to SEC rules regarding disclosures of non-GAAP financial measures, which would otherwise require a reconciliation of a non-GAAP financial measure to a GAAP financial measure. Reconciliations of non-GAAP financial measures were not relied upon by Goldman Sachs for purposes of its financial analyses and opinion or by the ProAssurance Board in connection with its consideration of the merger. ProAssurance has not provided reconciliations of the non-GAAP financial measures included in these projections to the comparable GAAP measure due to the lack of reasonably accessible or reliable comparable GAAP measures for these measures and the inherent difficulty in forecasting and quantifying the measures that are necessary for such reconciliation. Accordingly, a reconciliation of the financial measures is not included herein.

In considering the recommendation of the ProAssurance Board that you vote to approve the merger proposal, you should be aware that, aside from their interests as ProAssurance stockholders, ProAssurance’s directors and executive officers may have interests in the merger that are different from, or in addition to, the interests of ProAssurance stockholders generally, which may create potential conflicts of interest. These interests

are described in more detail below and, with respect to the named executive officers of ProAssurance, are quantified in the “Golden Parachute Compensation” table below. The ProAssurance Board was aware of these interests and considered them when it approved the merger agreement and the merger. The calculations set forth herein are based on the outstanding ProAssurance equity awards as of May 12, 2025.

ProAssurance’s named executive officers are Edward L. Rand, Jr., Dana S. Hendricks, Jeffrey P. Lisenby, Kevin M. Shook and Robert D. Francis.

With respect to ProAssurance’s executive officers, these interests are described in more detail below, assuming the merger occurs and, where applicable, the executive officer experiences a qualifying termination of employment on January 1, 2026:

As is the case for any stockholder of ProAssurance, ProAssurance’s directors and executive officers will receive $25.00 per share in cash, without interest, and less any applicable withholding taxes, for each share of ProAssurance common stock that they own at the effective time. For information regarding beneficial ownership of ProAssurance common stock by each of ProAssurance’s current directors, ProAssurance’s named executive officers and all directors and executive officers as a group, see the section of this proxy statement entitled “Security Ownership of Certain Beneficial Owners and Management” beginning on page 101.

As described in the section of this proxy statement entitled “The Merger Agreement—Treatment of ProAssurance Equity Awards” beginning on page 72, the merger agreement provides that the ProAssurance RSUs, ProAssurance performance shares and ProAssurance deferred shares will be treated as set forth below.

Special rules govern the treatment of ProAssurance RSUs that may be granted following the entry into the merger agreement as part of the 2026 long-term incentive award cycle, as further discussed in the section of this proxy statement entitled “The Merger Agreement—Employee Matters” beginning on page 86.

The following table sets forth the amounts that each of ProAssurance’s directors, named executive officers and all other executive officers would receive with respect to outstanding unvested ProAssurance RSUs and ProAssurance performance shares assuming the completion of the merger occurs on January 1, 2026. The numbers set forth below do not attempt to forecast any grants, additional issuances, dividends, additional deferrals or forfeitures of equity-based awards following May 12, 2025. The calculations set forth in the table below are based on outstanding unvested ProAssurance equity awards as of May 12, 2025 and the merger consideration of $25.00 (valuing all presently outstanding performance shares based on assumed target level performance, adjusting for rounding to the nearest quarter of a hundred, and disregarding the tranche of ProAssurance RSUs that are scheduled to vest on May 23, 2025). Depending on when the effective time occurs, certain ProAssurance equity awards shown in the table below may vest in accordance with their terms.

Each currently employed executive officer is eligible for severance benefits in specified circumstances, as set forth in each such executive officer’s employment agreement or release and severance agreement, as applicable. If any of the executive officers are terminated by ProAssurance without “cause” or resign for “good reason” (each as defined in the employment agreements or release and severance agreement, as applicable), subject to the execution and effectiveness of a separation agreement, including a general release of claims in favor of ProAssurance, the executive officers are entitled to receive (a) an amount equal to one times (two times in the case of Mr. Rand) the sum of the executive officer’s base salary and the average of the annual cash incentive awards and bonuses paid to the executive officer in each of the three complete calendar years prior to the executive officer’s termination of employment, payable in substantially equal installments over 12 months (36 months in the case of Mr. Rand) following the executive officer’s termination of employment, (b) if the executive officer elects continuation of health coverage under COBRA, continued health coverage at the active employees’ rate until the earlier of 12 months following the executive officer’s termination, the end of the executive officer’s COBRA health continuation period or the executive officer becomes eligible for substantially similar coverage under a subsequent employer’s group health plan (24 months in the case of Mr. Rand), (c) except for Mr. Rand, outplacement services customary to the executive officer’s position and (d) if the executive officers resign for good reason, full acceleration of vesting of the number of (i) unvested ProAssurance RSUs held by the executive officer, reduced by a fraction the denominator of which equals the number of whole months remaining in the executive officer’s restricted period and the numerator of which equals the number of whole months in the period commencing on the date of the executive officer’s termination and ending on the last vesting date and (ii) ProAssurance performance shares that would have been earned if the award period ended on December 31 of the year of the executive officer’s termination (based on the performance measures for the applicable award period), pro-rated by the number of months during the award period the executive officer was employed.

In addition, in lieu of the payments and benefits described in the preceding paragraph, in the event that any of the executive officers are terminated by ProAssurance without cause or resign for good reason, in either case within 24 months following a “change of control” (as defined in the employment agreements or release and severance agreement, as applicable) (at any point following a change of control for Mr. Rand), subject to the execution and effectiveness of a separation agreement, including a general release of claims in favor of ProAssurance, the executive officers are entitled to receive (a) an amount equal to two times the sum of the executive officer’s base salary plus the average of the annual cash incentive awards and bonuses paid to the executive officer in each of the three complete calendar years prior to the executive officer’s termination of employment, payable in substantially equal installments over 24 months (in a lump-sum in the case of Mr. Rand) following the executive officer’s termination of employment, (b) if the executive officer elects continuation of health coverage under COBRA, continued health coverage at the active employees’ rate until the earlier of 18 months following the executive officer’s termination of employment, the end of the executive officer’s COBRA health continuation period or the executive officer becomes eligible for substantially similar coverage under a subsequent employer’s group health plan (24 months in the case of Mr. Rand), (c) except for Mr. Rand, outplacement services customary to the executive officer’s position and (d) if the executive officers resign for good reason, full acceleration of vesting of the number of (i) unvested ProAssurance RSUs held by the executive officer, reduced by a fraction the denominator of which equals the number of whole months remaining in the executive officer’s restricted period and the numerator of which equals the number of whole months in the period commencing on the date of the executive officer’s termination and ending on the last vesting date and (ii) ProAssurance performance shares that would have been earned if the award period ended on December 31 of the year of the executive officer’s termination (based on the performance measures for the applicable award period), pro-rated by the number of months during the award period the executive officer was employed.

Mr. Rand’s employment agreement provides that if the payments or benefits payable to Mr. Rand in connection with a change in control would be subject to the excise tax on golden parachutes imposed under Section 4999 of the Code, then those payments or benefits will be reduced to mitigate the issues resulting from the application of Sections 280G and 4999 of the Code only if such reduction would result in a higher net after-tax benefit to such executive officer (the “Section 280G modified net cutback provisions”). Mr. Lisenby’s release and separation agreement provides that ProAssurance will provide Mr. Lisenby with a tax gross-up if the payments or benefits payable to Mr. Lisenby in connection with a change in control would be subject to the excise tax on golden parachutes imposed under Section 4999 of the Code such that Mr. Lisenby will retain 100% of the amount that Mr. Lisenby would have received in connection with such change in control if Section 4999 of the Code did not apply.

Pursuant to the terms of the merger agreement, ProAssurance’s directors and executive officers will be entitled to certain ongoing indemnification, expense advancement and insurance arrangements. See the section entitled “The Merger Agreement–Indemnification of Directors and Officers; Insurance” beginning on page 91 for a description of such ongoing arrangements.

Immediately prior to the effective time, ProAssurance shall, or shall cause its subsidiaries to, pay ProAssurance employees who are employed immediately prior to the effective time any unpaid annual bonus for completed performance periods and, with respect to any uncompleted performance period that includes the effective time, an amount at least equal to such ProAssurance employee’s target annual bonus for such performance period, pro-rated for any partial performance periods based on a fraction (a) the numerator of which is the number of days in the performance period that has elapsed through the effective time and (b) the denominator of which is the number of days in such performance period. With respect to the portion of the calendar year that includes the effective time that occurs after the effective time, The Doctors Company shall establish an annual bonus opportunity for such remaining portion of the calendar year that meets the requirements of the merger agreement.

For a period of at least 12 months following the effective time (or, if earlier, the date on which the continuing employee terminates employment), each continuing ProAssurance employee will be entitled to receive (a) a base salary or base wage rate that is no less favorable than the base salary or base wage rate provided to such continuing employee immediately prior to the effective time, (b) a target annual cash bonus, and commissions opportunity, that, in each case, is substantially comparable to (i) for the remainder of the calendar year in which the closing date occurs, the target annual cash bonus, and commissions opportunity, provided to such continuing employee immediately prior to the effective time, and (ii) for the portion of the twelve (12) months that occurs in the calendar year following the calendar year in which the closing date occurs, the target annual cash bonus opportunity and commissions opportunity provided to similarly situated employees of The Doctors Company and its affiliates, (c) employee benefits (in each case, excluding defined benefit pension, deferred compensation, retiree medical, change in control, retention, and equity and equity-based compensation benefits) that are substantially comparable to either (i) the employee benefits provided to such continuing employee immediately prior to the effective time, or (ii) the employee benefits provided to similarly situated employees of The Doctors Company and its affiliates, and (d) a severance or termination arrangement that is no less favorable than the severance or termination arrangement provided to such continuing employee immediately prior to the effective time.

As of the date of this proxy statement, other than the arrangements discussed in this proxy statement, none of ProAssurance’s executive officers have entered into any agreement with The Doctors Company regarding employment with, compensation from, or equity participation or reinvestment in, the surviving corporation or The Doctors Company on a going-forward basis following the completion of the merger. However, The Doctors Company (or its representatives) and some or all of ProAssurance’s executive officers may from time to time have discussions with respect to, or enter into, such arrangements.

ProAssurance may, in consultation with The Doctors Company, take certain actions before the effective time to mitigate the amount of potential “excess parachute payments” for “disqualified individuals” (each as defined in Section 280G of the Code).

ProAssurance may implement the following strategies to mitigate any issues resulting from the application of Section 280G and 4999 of the Code and to maximize the net after-tax proceeds received by any individual subject to Section 4999 of the Code: (a) accelerate the vesting or payment of compensation (including annual bonuses) that is scheduled to vest or be paid in calendar year 2026, (b) accelerate the vesting or payment of compensation that would vest or become payable at the effective time in accordance with the applicable employment agreement or the terms of the applicable ProAssurance plan, or (c) enter into or expand non-competition agreements and obtain valuations with respect to such non-competition agreements.

Mr. Lisenby’s release and separation agreement provides that ProAssurance will provide Mr. Lisenby with a tax gross-up if the payments or benefits payable to Mr. Lisenby in connection with a change in control would be subject to the excise tax on golden parachutes imposed under Section 4999 of the Code such that Mr. Lisenby will retain 100% of the amount that Mr. Lisenby would have received in connection with such change in control if Section 4999 of the Code did not apply.

ProAssurance may grant additional RSUs, including to its executive officers, following the entry into the merger agreement as part of the 2026 long-term incentive award cycle, as further discussed in the section of this proxy statement entitled “The Merger Agreement—Employee Matters” beginning on page 86. No such awards have been granted as of the date hereof.

ProAssurance may grant cash-based retention bonus awards to employees not to exceed an aggregate amount agreed with The Doctors Company or 100% of any individual recipient’s annual base salary among certain employees, with the retention awards to become payable upon the closing date, subject to the award recipients’ continued employment through the closing date. See the section of this proxy statement entitled “The Merger Agreement—Employee Matters” beginning on page 86.

The following table sets forth the information required by Item 402(t) of Regulation S-K regarding the compensation for ProAssurance’s named executive officers based on the merger, assuming that (a) the merger is completed on January 1, 2026, (b) each named executive officer experiences a qualifying termination of employment immediately following the completion of the merger, (c) each named executive officer’s base salary rate, target annual bonus and benefits levels remain unchanged from those in effect as of the date of this proxy statement, (d) each named executive officer’s ProAssurance equity awards remain unchanged as of May 12, 2025 and (e) the merger consideration is $25.00 per share. The actual amounts payable would depend on the date of termination, the manner of the termination and the terms of the agreements in effect at such time. The calculations in the table below neither include amounts that ProAssurance’s named executive officers were already entitled to receive or were vested in as of the date of this proxy statement, nor do they include amounts under contracts, agreements, plans or arrangements to the extent they do not discriminate in scope, terms or operation in favor of the named executive officers and are available generally to all the salaried employees of ProAssurance. Additionally, the calculations do not reflect any possible reductions under the Section 280G modified net cutback provisions described above in the section entitled “The Merger Proposal (Proposal 1)—Interests of ProAssurance’s Executive Officers and Directors in the Merger—Severance Benefits” on page 60, and the amounts listed below assume that no Section 280G tax gross up amount will be payable to Mr. Lisenby. These amounts do not include any amounts payable in respect of any issuances or forfeitures of ProAssurance equity awards that may be made or occur after May 12, 2025 and prior to the completion of the merger, and do not reflect any ProAssurance equity awards that have vested or are expected to vest in accordance with their terms prior to the completion of the merger. As a result of the foregoing assumptions, which may or may not actually occur or be accurate on the relevant date, including the assumptions described in the footnotes to the table, the actual amounts, if any, to be received by a named executive officer may materially differ from the amounts set forth below.

Under the merger agreement and subject to certain limitations, each of ProAssurance and The Doctors Company has agreed to use their respective reasonable best efforts to, among other things, consummate the merger as soon as reasonably practicable. Completion of the merger is conditioned upon (a) the expiration or early termination of the waiting period (and any extension thereof) applicable to the consummation of the merger under the HSR Act, (b) the expiration or termination of any voluntary agreement with a governmental entity entered into by ProAssurance, The Doctors Company or Merger Sub not to consummate the merger and (c) the receipt of each other consent, approval or clearance with respect to, or termination or expiration of any

applicable waiting period (and any extensions thereof) imposed under, any antitrust or insurance laws with respect to the merger as specified in the applicable exhibit to the merger agreement, which consents, approvals and clearances are described below in the sections entitled “The Merger Proposal (Proposal 1) – U.S. Insurance Regulatory Approvals” and “The Merger Proposal (Proposal 1) – Non-U.S. Insurance Regulatory Approvals” beginning on page 65.

Under the HSR Act, the merger may not be completed until notifications have been filed with and certain information has been furnished to the Antitrust Division and the FTC and all statutory waiting period requirements have been satisfied. ProAssurance and The Doctors Company plan to file an HSR notification with the Antitrust Division and the FTC as promptly as reasonably practicable.

At any time before or after the completion of the merger, the Antitrust Division or the FTC could take action under the U.S. antitrust laws, including seeking to prevent the merger, to rescind the merger or to clear the merger subject to the divestiture of assets of ProAssurance or The Doctors Company or subject to other remedies. In addition, U.S. state attorneys general could take action under the antitrust laws as they deem necessary or desirable in the public interest, including without limitation seeking to enjoin the completion of the transactions or permitting completion subject to the divestiture of assets of ProAssurance or The Doctors Company or other remedies. Private parties may also seek to take legal action under the antitrust laws under some circumstances. There can be no assurance that a challenge to the transactions on antitrust grounds will not be made or, if such challenge is made, that it would not be successful.

Insurance laws and regulations generally provide that no person may directly or indirectly acquire control of an insurance company unless and until that acquisition has been approved by the relevant domiciliary insurance regulator of that insurance company. Pursuant to those laws and regulations, The Doctors Company will file applications for prior approval or prior notifications relating to the various insurance company subsidiaries of ProAssurance with a number of state insurance regulators in the United States, Lloyd’s of London in the United Kingdom, and ProAssurance will file an application for prior approval relating to certain insurance company subsidiaries of ProAssurance with the Cayman Islands Monetary Authority (collectively, the “insurance regulators”). A filing will also be made by The Doctors Company seeking non-disapproval of the insurance department of the State of Texas relating to the change of control of ProAssurance’s subsidiaries that are licensed as insurance agencies in Texas.

Further, pursuant to the insurance laws and regulations of certain U.S. states, The Doctors Company will provide a prior notification to a number of applicable insurance regulatory authorities regarding the likely impact of the merger on market competition in its state.

Under the merger agreement and subject to certain limitations, ProAssurance and The Doctors Company have both agreed to use their reasonable best efforts to complete the merger, including obtaining any requisite antitrust approval and insurance regulatory approval, as soon as reasonably practicable. With respect to any approvals relating to antitrust laws or insurance laws, ProAssurance and The Doctors Company have also agreed to (a) consult and cooperate in all respects with each other in connection with any filing or submission and in connection with any investigation or other inquiry, including any proceeding initiated by a private party,

(b) subject to applicable law, furnish to the other party as promptly as reasonably practicable all information required for any application or other filing to be made by the other party pursuant to any applicable law in connection with the transactions contemplated by the merger agreement, (c) promptly notify the other party of any substantive communication received by the FTC, the Antitrust Division, the Insurance Regulators or any other governmental entity and of any substantive communication received or given in connection with any proceeding by a private party, in each case regarding any of the transactions contemplated by the merger agreement and, subject to applicable law, furnish the other party promptly with copies of all correspondence, filings and communications between them and the FTC, the Antitrust Division, the Insurance Regulators or any other governmental entity with respect to the transactions contemplated by the merger agreement, (d) respond as promptly as reasonably practicable to any inquiries received from, and supply as promptly as reasonably practicable any additional information or documentation that may be requested by the FTC, the Antitrust Division, the Insurance Regulators or by any other governmental entity in respect of such registrations, declarations and filings or such transactions, and (e) permit the other party to review any substantive communication given by it to, and consult with each other in advance, and consider in good faith the other party’s reasonable comments in connection with, any filing, notice, application, submission, communication, meeting or conference with, the FTC, the Antitrust Division, the Insurance Regulators or any other governmental entity or, in connection with any proceeding by a private party, with any other person. No party shall independently participate in any substantive meeting or communication with any governmental entity in respect of any such filings, investigation or other inquiry related to the parties’ efforts to close, including covenants with respect to regulatory matters, without giving the other parties sufficient prior notice of the meeting and, to the extent permitted by such governmental entity, the opportunity to attend and/or participate in such substantive meeting or communication. ProAssurance shall not commit to or agree with any governmental entity to stay, toll or extend any applicable waiting period, “pull-and-refile” pursuant to 16 C.F.R. 804.16 any filing made under the HSR Act, enter into a timing agreement, including any agreement to delay the consummation or not to consummate the transactions, or take any similar action, without the prior written consent of The Doctors Company. The parties to the merger agreement agreed that The Doctors Company shall control and direct (and ProAssurance shall cooperate with The Doctors Company in connection with) all strategy and decisions with respect to obtaining all approvals or other clearances under any applicable antitrust, foreign investment or insurance law, including all filings (including where to file and the timing of such filings) and any withdrawals and/or refiling thereof, strategies, processes, negotiation of settlements (if any), and related proceedings contemplated by the merger agreement, including for the avoidance of doubt the marketing or sale of any part of ProAssurance’s, The Doctors Company’s or any of their respective affiliates’ businesses or assets; provided, however, that The Doctors Company shall provide ProAssurance a reasonable opportunity to consult and consider such strategy and decisions and The Doctors Company will consider ProAssurance’s input and views with respect thereto in good faith (including with respect to any stay, toll or extension, “pull-and-refile”, entry into a timing agreement or any similar action described in the immediately preceding sentence). No such approvals, clearances or filings related to any foreign investment laws have been identified.

The Doctors Company is required to take any and all steps necessary, proper or advisable to (a) resolve, avoid, or eliminate impediments or objections, if any, that may be asserted with respect to the transactions contemplated by the merger agreement under any antitrust law, foreign investment or insurance law or (b) avoid the entry of, effect the dissolution of, and have vacated, modified, suspended, eliminated, lifted, reversed or overturned, any decree, decision, determination, order or judgment entered or issued under any antitrust, foreign investment or insurance law, or that becomes reasonably foreseeable to be entered or issued, that would, or would reasonably be expected to, prevent, restrain, enjoin, prohibit, make unlawful, restrict or delay the consummation of the contemplated transactions, so as to enable the parties to the merger agreement to close the transactions contemplated by the merger agreement as expeditiously as practicable (but in no event later than the end date), including (a) the defense through litigation on the merits of any antitrust, foreign investment or insurance law claim seeking to delay, restrain, prevent, enjoin or otherwise prohibit consummation of the transactions contemplated by the merger agreement, and (b) (i) proposing, negotiating, committing to, agreeing to and effecting, by consent decree, hold separate orders or otherwise, the sale, lease, divesture, disposition, or license (or holding separate pending such disposition) of any assets, operations, rights, product lines, licenses, properties, products, rights, services or businesses of The Doctors Company, any of The Doctor Company’s subsidiaries and affiliates (collectively, “The Doctors Company Group”) or ProAssurance or its subsidiaries or any interest therein, (ii) otherwise taking or committing or agreeing to restrictions or actions that after the effective time would limit The Doctors Company’s or any member of The Doctors Company Group or

ProAssurance’s or its subsidiaries’ freedom of action or operations with respect to, or their ability to retain, any assets, operations, rights, product lines, licenses, properties, products, rights, services or any interest or interests therein, including any rate freeze, rate decrease or restrictions to compete, or any capital contribution, capital support agreement, guarantee, keepwell or other similar capital maintenance undertaking (including to maintain a minimum risk-based capital level or rating), restrictions on dividends or distributions or (iii) agreeing to enter into, modify or terminate existing contractual relationships, contractual rights or contractual obligations, and promptly effecting the sale, lease, license, divestiture, disposal and holding separate of, assets, operations, rights, product lines, licenses, properties, products, rights, services or businesses of The Doctors Company or any member of The Doctors Company Group or ProAssurance or its subsidiaries or any interest or interests therein and the entry into agreements with, and submission to orders of, the relevant governmental entity giving effect thereto or to such restrictions or actions. Notwithstanding anything to the contrary set forth in the merger agreement, neither The Doctors Company nor any member of The Doctors Company Group shall be obligated to undertake or become subject to any burdensome condition (as defined in the section of this proxy statement entitled “The Merger Agreement – Efforts to Consummate the Merger” beginning on page 87).

Although ProAssurance has reason to believe it will complete the antitrust reviews and insurance reviews in a timely manner, there is no certainty that these reviews will be completed within the period of time contemplated by the merger agreement. ProAssurance has no reason to believe that the completion of any of such reviews would be conditioned upon actions that would be materially adverse to ProAssurance or The Doctors Company, or that a challenge to the merger would be made. If a challenge is made, however, the results of such challenge cannot be predicted. Private parties or U.S. state attorneys general may also bring actions under the antitrust, insurance and other laws under certain circumstances. Further, antitrust or insurance regulatory approvals or clearances do not constitute an endorsement or recommendation of the merger.

The exchange of ProAssurance common stock for cash in the merger generally will be a taxable transaction for U.S. federal income tax purposes. In general, a U.S. holder (as defined in the section of this proxy statement entitled “Material U.S. Federal Income Tax Consequences of the Merger” beginning on page 103) whose shares of ProAssurance common stock are converted into the right to receive cash in the merger will recognize capital gain or loss for U.S. federal income tax purposes in an amount equal to the difference, if any, between the amount of cash received with respect to such shares and the U.S. holder’s adjusted tax basis in such shares at the time of the exchange. Gain or loss will be determined separately for each block of shares of ProAssurance common stock (i.e., shares of ProAssurance common stock acquired at the same cost in a single transaction). The determination of the actual tax consequences of the merger to a holder of ProAssurance common stock will depend on the holder’s specific situation.

The tax consequences of the merger to you will depend on your particular circumstances. You should read the section of this proxy statement entitled “Material U.S. Federal Income Tax Consequences of the Merger” beginning on page 103 and consult your tax advisors regarding the U.S. federal income tax consequences of the merger to you in your particular circumstances, as well as tax consequences arising under the laws of any state, local or foreign taxing jurisdiction.

As promptly as reasonably practicable following the completion of the merger, the ProAssurance common stock currently listed on NYSE will cease to be listed on NYSE and will be deregistered under the Exchange Act.

Under the DGCL, ProAssurance stockholders have the right to demand appraisal and to receive payment in cash for the fair value of their shares of ProAssurance common stock as determined by the Delaware Court of Chancery, together with interest, if any, as determined by the Delaware Court of Chancery, in lieu of the merger consideration, subject to the requirements and limitations set forth in Section 262 of the DGCL described herein. These rights are known as appraisal rights. ProAssurance stockholders of record and beneficial owners electing to exercise appraisal rights must comply with the provisions of Section 262 of the DGCL in order to perfect their

rights. Strict compliance with the statutory procedures is required to perfect appraisal rights under Delaware law. This section is intended as a brief summary of the material provisions of Delaware law pertaining to appraisal rights. The following discussion, however, is not a complete summary of the law pertaining to appraisal rights under the DGCL and is qualified in its entirety by the full text of Section 262 of the DGCL, which is attached to this proxy statement as Annex C and incorporated into this proxy statement by reference. A copy of Section 262 may also be accessed without subscription or cost at the following publicly available website: https://delcode.delaware.gov/title8/c001/sc09/index.html#262. Failure to comply strictly with the procedures set forth in Section 262 of the DGCL will result in the loss of appraisal rights. The following discussion does not constitute any legal or other advice, nor does it constitute a recommendation as to whether or not a ProAssurance stockholder of record or beneficial owner should exercise his, her or its right to seek appraisal under Section 262 of the DGCL.

Subject to certain exceptions specified in Section 262 of the DGCL and summarized below, holders of record, and beneficial owners, of shares of ProAssurance common stock who: (a) submit a written demand for appraisal of such person’s shares to ProAssurance prior to the vote on the merger agreement; (b) have not consented to or otherwise voted in favor of the merger agreement or otherwise withdrawn, lost or waived appraisal rights; (c) continuously are the record holders or beneficial holders, as applicable, of such shares through the effective time; and (d) otherwise comply with the applicable procedures and requirements set forth in Section 262 of the DGCL will be entitled to have their shares appraised by the Delaware Court of Chancery and receive payment in cash of the “fair value” of such shares (as determined by the Delaware Court of Chancery, exclusive of any element of value arising from the accomplishment or expectation of the merger) as of the completion of the merger instead of the merger consideration. Any such ProAssurance stockholder of record or beneficial holder awarded “fair value” for the holder’s shares by the court would receive payment of that fair value in cash, together with interest, if any, in lieu of the right to receive the merger consideration. It is possible that any such “fair value” as determined by the Delaware Court of Chancery may be more or less than, or the same as the merger consideration.

Section 262 of the DGCL requires that ProAssurance stockholders for whom appraisal rights are available be notified not less than 20 days before the special meeting. Either a copy of Section 262 of the DGCL or information directing ProAssurance stockholders to a publicly available electronic resource at which Section 262 of the DGCL may be accessed without subscription or cost must be included with such notice.

This proxy statement constitutes our notice to ProAssurance stockholders of the availability of appraisal rights in connection with the merger in compliance with the requirements of Section 262 of the DGCL, which is attached to this proxy statement as Annex C and incorporated into this proxy statement by reference. A copy of Section 262 may also be accessed without subscription or cost at the following publicly available website: https://delcode.delaware.gov/title8/c001/sc09/index.html#262. ProAssurance stockholders of record and beneficial owners who wish to exercise appraisal rights or who wish to preserve the right to do so should review the following summary and the applicable statutory provisions carefully. Failure to comply with the procedures of Section 262 of the DGCL in a timely and proper manner will result in the loss of appraisal rights. In addition, the Delaware Court of Chancery will dismiss appraisal proceedings in respect of ProAssurance unless certain stock ownership conditions are satisfied by ProAssurance stockholders of record and beneficial owners seeking appraisal. Because of the complexity of the procedures for exercising the right to seek appraisal, ProAssurance stockholders of record and beneficial owners who wish to exercise appraisal rights are urged to consult with their own legal and financial advisors in connection with compliance under Section 262 of the DGCL. A ProAssurance stockholder of record or beneficial owner who loses, waives or otherwise fails to properly exercise his, her or its appraisal rights will be entitled to receive the merger consideration.

If you are a ProAssurance stockholder of record or a beneficial holder and wish to exercise the right to seek an appraisal of your shares of ProAssurance common stock, you must satisfy each of the following conditions:

You must deliver to ProAssurance a written demand for appraisal before the vote on approval of the merger agreement at the special meeting. This written demand for appraisal must be in addition to and separate from any proxy or vote abstaining from or voting against the merger agreement. Voting against or failing to vote for the merger agreement by itself does not constitute a demand for appraisal within the meaning of Section 262 of the

DGCL. The demand must reasonably inform us of the identity of the ProAssurance stockholder of record or beneficial holder and the intention of such holder to demand appraisal of his, her or its shares. A failure by such holder to make a written demand for appraisal before the vote with respect to the merger agreement is taken will constitute a waiver of appraisal rights.

If you fail to comply with any of these conditions and the merger is completed, you will be entitled to receive the merger consideration, but you will have no appraisal rights with respect to your shares of ProAssurance common stock.

In addition, because shares of ProAssurance common stock are listed on a national securities exchange and are expected to continue to be listed on such exchange immediately prior to the consummation of the merger, the Delaware Court of Chancery will dismiss appraisal proceedings as to all shares of ProAssurance common stock, unless (a) the total number of shares entitled to appraisal exceeds 1% of the outstanding shares of ProAssurance common stock or (b) the value of the merger consideration for such total number of shares entitled to appraisal exceeds $1 million (collectively, the “ownership thresholds”). At least one of the ownership thresholds must be met in order for ProAssurance stockholders to be entitled to seek appraisal with respect to such shares of ProAssurance common stock.

In the case of a record holder of shares of ProAssurance common stock, voting, via the internet during the special meeting or by proxy, against, abstaining from voting on or failing to vote on the merger agreement will not constitute a written demand for appraisal as required by Section 262 of the DGCL. The written demand for appraisal is in addition to and separate from any proxy or vote. If you want to exercise your appraisal rights, you must not vote your shares of ProAssurance common stock via the internet during the special meeting or by proxy in favor of the merger agreement.

In the case of a beneficial owner of shares of ProAssurance common stock, brokers, banks and other nominees that hold shares in “street name” for their customers do not have discretionary authority to vote those shares on the merger agreement without specific voting instructions from the beneficial owner on such proposal, but such brokers, banks or other nominees will vote such shares as instructed if the beneficial owner provides such instructions. If a beneficial owner of shares of ProAssurance common stock held in “street name” instructs such person’s broker, bank or other nominee to vote such person’s shares in favor of the merger agreement, and does not revoke such instruction prior to the vote on the merger agreement, then such shares will be voted in favor of the merger agreement, and it will constitute a waiver of such beneficial owner’s right of appraisal and will nullify any previously delivered written demand for appraisal. Therefore, if you are a beneficial owner of shares of ProAssurance common stock who wishes to exercise appraisal rights, you must either not provide any instructions to your broker, bank or other nominee how to vote on the merger agreement or instruct such broker, bank or other nominee to vote against the merger agreement or abstain from voting on such proposal.

A holder of record or beneficial owner of shares of ProAssurance common stock issued and outstanding immediately prior to the effective time may assert appraisal rights for the shares of ProAssurance common stock held of record or beneficially in that holder’s name. A demand for appraisal must be executed by or on behalf of the ProAssurance stockholder of record or beneficial owner, as applicable, and must reasonably inform ProAssurance of the identity of the ProAssurance stockholder of record or beneficial owner and that the ProAssurance stockholder intends to demand appraisal of his, her or its shares of ProAssurance common stock. In addition, in the case of a demand for appraisal made by a beneficial owner, the demand must (a) reasonably identify the holder of record of the shares for which the demand is made, (b) provide documentary evidence of such beneficial owner’s beneficial ownership and a statement that such documentary evidence is a true and correct copy of what it purports to be and (c) provide an address at which such beneficial owner consents to receive notices given by ProAssurance and to be set forth on the verified list of persons who have demanded appraisal for their shares pursuant to Section 262(f) of the DGCL. A holder of record, such as a bank, broker or other nominee, who holds shares of ProAssurance common stock as a nominee or intermediary for others, may exercise his, her or its right of appraisal with respect to the shares held for one or more beneficial owners, while not exercising this right for other beneficial owners. In that case, the written demand should state the number of shares as to which appraisal is sought. Where no number of shares is expressly mentioned, the demand will be presumed to cover all shares held in the name of the holder of record.

If you elect to exercise appraisal rights under Section 262 of the DGCL, you should mail or deliver a written demand to:

The following discussion sets forth the principal terms of the merger agreement, a copy of which is attached as Annex A to this proxy statement and is incorporated by reference herein. The rights and obligations of the parties are governed by the express terms and conditions of the merger agreement and not by this discussion, which is summary by nature. This discussion is not complete and is qualified in its entirety by reference to the complete text of the merger agreement. You are encouraged to read the merger agreement carefully in its entirety, as well as this proxy statement and any documents incorporated by reference herein, before making any decisions regarding the merger.

The merger agreement and this summary of its terms have been included to provide you with information regarding the terms of the merger agreement. Factual disclosures about ProAssurance contained in this proxy statement or in ProAssurance’s public reports filed with the SEC may supplement, update or modify the factual disclosures about ProAssurance contained in the merger agreement and described in this summary. The representations, warranties and covenants made in the merger agreement by ProAssurance, The Doctors Company and Merger Sub were qualified and subject to important limitations agreed to by ProAssurance, The Doctors Company and Merger Sub in connection with negotiating the terms of the merger agreement. In particular, in your review of the representations and warranties contained in the merger agreement and described in this summary, it is important to bear in mind that the representations and warranties were negotiated with the principal purposes of establishing the circumstances in which a party to the merger agreement may have the right not to close the merger if the representations and warranties of the other party prove to be untrue, due to a change in circumstance or otherwise, and allocating risk between the parties to the merger agreement, and were not intended by the parties to the merger agreement to be a characterization of the actual state of facts or condition of ProAssurance, The Doctors Company or Merger Sub, except as expressly stated in the merger agreement. The representations and warranties may also be subject to a contractual standard of materiality different from those generally applicable to stockholders and reports and documents filed with the SEC, and in some cases were qualified by disclosures that were made by ProAssurance to The Doctors Company and Merger Sub, which disclosures are not reflected in the merger agreement. Moreover, information concerning the subject matter of the representations and warranties, which do not purport to be accurate as of the date of this proxy statement, may have changed since the date of the merger agreement and subsequent developments or new information qualifying a representation or warranty may have been included in this proxy statement or in the public filings made by ProAssurance with the SEC.

Additional information about ProAssurance may be found elsewhere in this proxy statement and ProAssurance’s other public filings. See “Where You Can Find Additional Information” beginning on page 108 of this proxy statement.

The closing of the merger will take place at the offices of Simpson Thacher & Bartlett LLP, 425 Lexington Avenue, New York, New York 10017, or remotely by exchange of documents and signatures (or their electronic counterparts), at 9:00 a.m. (New York City time) on the third business day after the satisfaction or (to the extent permitted by applicable law) waiver of the conditions set forth in the merger agreement (other than those conditions that by their nature are to be satisfied at the closing, but subject to the satisfaction or (to the extent permitted by applicable law) waiver of such conditions), unless another time or place is agreed to in writing by ProAssurance and The Doctors Company.

At the closing, ProAssurance and The Doctors Company will cause the merger to be consummated by filing a certificate of merger with respect to the merger (the “certificate of merger”), to be executed, acknowledged and filed with the Secretary of State of the State of Delaware in accordance with Section 251 of the DGCL and shall make all other filings or recordings required under the DGCL to consummate the merger. The merger shall become effective at the time when the certificate of merger has been duly filed with the Secretary of State of the State of Delaware or at such later time as may be agreed by ProAssurance and The Doctors Company in writing and specified in the certificate of merger in accordance with the DGCL.

Upon the terms and conditions of the merger agreement, and in accordance with the DGCL, at the effective time, Merger Sub will merge with and into ProAssurance and the separate corporate existence of Merger Sub will cease, with ProAssurance continuing as the surviving corporation. At the effective time, (a) the certificate of incorporation of ProAssurance, as in effect immediately prior to the effective time, shall be amended and restated in its entirety, and, as so amended and restated, shall be the certificate of incorporation of the surviving corporation, until thereafter amended and (b) without any further action on the part of ProAssurance or Merger Sub, the bylaws of Merger Sub as in effect immediately prior to the effective time, shall be the bylaws of the surviving corporation (except that references therein to the name of Merger Sub shall be replaced by references to the name of ProAssurance) until thereafter amended or restated as provided therein.

The board of directors of the surviving corporation immediately following the effective time shall consist of the members of the board of directors of Merger Sub at the effective time, until their successors have been duly elected or appointed and qualified or until their earlier death, resignation or removal in accordance with the certificate of incorporation and the bylaws of the surviving corporation and applicable law. The officers of ProAssurance at the effective time will be the initial officers of the surviving corporation and will hold office until their respective successors are duly elected or appointed and qualified, or until their earlier death, resignation or removal, in accordance with the surviving corporation’s certificate of incorporation and bylaws and applicable law.

At the effective time, each share of ProAssurance common stock issued and outstanding immediately prior to the effective time (other than cancelled shares, non-cancelled subsidiary shares and dissenting shares, as described in the merger agreement) will be converted into the right to receive the merger consideration. From and after the effective time, such ProAssurance common stock will no longer be outstanding and will automatically be cancelled and extinguished, and will cease to exist, and each former holder of certificates or book-entry shares, which immediately prior to the effective time represented such ProAssurance common stock, will cease to have any rights with respect thereto, except for the right to receive, upon surrender of such certificates or book-entry shares, the merger consideration.

Each cancelled share will cease to be outstanding, will be automatically cancelled and retired, and no consideration or payment will be delivered in exchange for such shares. Each non-cancelled subsidiary share issued and outstanding immediately prior to the effective time will be converted into and become a proportionally equivalent amount of issued, fully paid and non-assessable shares of the surviving corporation.

The merger agreement provides that outstanding ProAssurance equity awards will be treated as set forth below.

Restricted Stock Units. Immediately prior to the effective time, each outstanding unvested ProAssurance RSU will generally, automatically and without any required action on the part of the holder thereof, be immediately vested and be cancelled and will entitle the holder of such ProAssurance RSU to receive, at or promptly after the closing date, an amount in cash, without interest, equal to the product of (a) the total number of shares of ProAssurance common stock subject to the ProAssurance RSU multiplied by (b) $25.00, less applicable tax withholdings.

Performance Shares. Immediately prior to the effective time, each outstanding unvested ProAssurance performance share will, automatically and without any required action on the part of the holder thereof, be immediately vested and be cancelled and will entitle the holder of such ProAssurance performance share to receive, at or promptly after the closing date, an amount in cash, without interest, equal to the product of (a) the total number of shares of ProAssurance common stock subject to the ProAssurance performance share, calculated based on target-level performance multiplied by (b) $25.00, less applicable tax withholdings.

Deferred Shares. Immediately prior to the effective time, all awarded ProAssurance deferred shares will, automatically and without any required action on the part of the holder thereof, be converted into an obligation to pay cash and will entitle the holder of such ProAssurance deferred shares to receive, at or promptly after the closing date, an amount in cash, without interest, equal to the product of (a) the total number of shares of ProAssurance common stock subject to the ProAssurance deferred shares multiplied by (b) $25.00.

Any consideration payable in respect of the ProAssurance RSUs, ProAssurance performance shares and ProAssurance deferred shares will be paid through the payroll system or payroll provider (to the extent applicable) of the surviving corporation as promptly as reasonably practicable following the closing date, but in no event later than seven business days following the closing date. Notwithstanding the foregoing, if any payment owed to a holder of ProAssurance RSUs, ProAssurance performance shares or ProAssurance deferred shares cannot be made through the surviving corporation’s payroll system or payroll provider, then the surviving corporation will issue a wire transfer or direct deposit, or a check for such payment to such holder as promptly as practicable following the closing date but in no event later than five business days thereafter.

Special rules govern the treatment of ProAssurance RSUs that may be granted following the entry into the merger agreement as part of the 2026 long-term incentive award cycle, as further discussed in the section of this proxy statement entitled “The Merger Agreement—Employee Matters” beginning on page 86.

At or prior to the effective time, The Doctors Company will deposit, or cause to be deposited, with a paying agent designated by The Doctors Company and reasonably acceptable to ProAssurance, cash in an amount sufficient to pay the aggregate merger consideration except that, with respect to any dissenting shares, The Doctors Company will not be required to deposit or cause to be deposited with the paying agent funds sufficient to pay the per share merger consideration that would be payable in respect of such dissenting shares if such dissenting shares were not dissenting shares. Promptly after the effective time (and in any event within three business days after the effective time), the surviving corporation will cause the paying agent to mail or otherwise provide to each former holder of record of certificates that immediately prior to the effective time represented outstanding shares of ProAssurance common stock and each former holder of record of shares of ProAssurance common stock held in book-entry form (in each case, other than holders of only cancelled shares and dissenting shares, as described in the merger agreement) (a) transmittal materials, including a letter of transmittal, which will specify that delivery of certificates will be effected, and risk of loss and title to the certificates will pass only upon delivery of the certificates (or effective affidavits in lieu thereof in accordance with the merger agreement) and a duly completed and validly executed letter of transmittal with respect to such certificates to the paying agent, or, in the case of book-entry shares, only upon delivery of an “agent’s message,” (or such other evidence, if any, of the book-entry transfer as the paying agent may reasonably request) to the paying agent, such transmittal materials to be in a form and have such other provisions as ProAssurance and The Doctors Company may reasonably agree, and (b) instructions for use in effecting the surrender of the certificates or book-entry shares, as applicable, in exchange for cash in an amount equal to the product of the per share merger consideration multiplied by the number of shares of ProAssurance common stock previously represented by such certificates.

Following the effective time, upon surrender of a certificate (or an effective affidavit of loss in lieu thereof) for cancellation to the paying agent, together with such letter of transmittal duly completed and validly executed in accordance with the instructions thereto, the holder of such certificate will be entitled to receive in exchange therefor as promptly as reasonably practicable after such surrender following the effective time, a cash payment in an amount (after giving effect to any required tax withholding) equal to the product of the per share merger consideration multiplied by the number of shares of ProAssurance common stock previously represented by such certificate and the certificate (or affidavit of loss in lieu thereof) so surrendered will immediately be cancelled. Each book-entry share representing shares of ProAssurance common stock (other than cancelled shares and dissenting shares, as described in the merger agreement) will be entitled to receive, and The Doctors Company will cause the paying agent to pay and deliver in exchange therefor as promptly as reasonably practicable after the paying agent’s receipt of an “agent’s message” or such other evidence, if any, as the paying agent may reasonably request following the effective time, a cash payment in an amount equal to the product of the per share merger consideration multiplied by the number of shares of ProAssurance common stock previously represented by such book-entry share and the book-entry shares so surrendered will be cancelled. The paying agent will accept such certificates (or affidavits of loss in lieu thereof) and make such payments and deliveries with respect to book-entry shares upon compliance with such reasonable terms and conditions as the paying agent may impose to effect an orderly exchange thereof in accordance with customary exchange practices. No interest will be paid or accrued for the benefit of holders of the certificates or book-entry shares on any amount payable upon the surrender or delivery thereof.

The merger agreement contains representations and warranties made by ProAssurance to The Doctors Company and Merger Sub and by The Doctors Company and Merger Sub to ProAssurance. Certain of the representations and warranties in the merger agreement are subject to materiality or material adverse effect qualifications (that is, they will not be deemed to be inaccurate or incorrect unless their failure to be true or correct (a) is material, (b) would result in a material adverse effect on the party making such representation or warranty or (c) would have a material adverse effect on the ability to consummate, or prevent the consummation of, the transactions). In addition, certain of the representations and warranties in the merger agreement are subject to knowledge qualifications, which means that those representations and warranties would not be deemed untrue, inaccurate or incorrect as a result of matters of which certain individuals from the party making the representation (who are specified in qualifying the “knowledge” of such party for purposes of the merger agreement) did not have actual knowledge. Furthermore, each of the representations and warranties is subject to the qualifications set forth on the disclosure letter delivered to The Doctors Company by ProAssurance in connection with the merger agreement (the “disclosure letter”), in the case of certain representations and warranties made by ProAssurance, as well as the reports of ProAssurance filed with or furnished to the SEC during the period from January 1, 2024 through March 18, 2025 (excluding any disclosures set forth under the captions “Risk Factors” or “Forward-Looking Statements” and in any other section to the extent they are cautionary, predictive or forward-looking in nature).

In the merger agreement, ProAssurance has made representations and warranties to The Doctors Company and Merger Sub regarding:

In the merger agreement, The Doctors Company and Merger Sub have made representations and warranties to ProAssurance regarding:

For purposes of the merger agreement, a “material adverse effect” on ProAssurance means any event, development, change, effect or occurrence (“effect”) that, individually or in the aggregate, has a material adverse effect on or with respect to the assets, business, results of operation or financial condition of ProAssurance and its subsidiaries taken as a whole, provided that no effects relating to, arising out of or in connection with or resulting from any of the following shall be deemed, either alone or in combination with any of the following, to constitute or contribute to a material adverse effect or be taken into account in determining whether a material adverse effect has occurred or would reasonably be expected to occur:

The merger agreement provides that, subject to certain exceptions in the disclosure letter, during the period from March 19, 2025 to the effective time (or, if earlier, the date, if any, on which the merger agreement is terminated by its terms) and except as required or expressly provided by the merger agreement, as required by applicable laws or except as consented to in writing by The Doctors Company (which consent may not be unreasonably withheld, conditioned or delayed), (a) ProAssurance will and will cause its subsidiaries to, conduct the business of ProAssurance and its subsidiaries in the ordinary and usual course of business consistent in all material respects with past practice and use its and their respective commercially reasonable efforts to preserve substantially intact its and their respective business organizations and material business relationships with customers, suppliers, creditors, lessors and other persons with whom ProAssurance and its subsidiaries have material business relationships, and (b) ProAssurance will not and will cause each of its subsidiaries not to:

Notwithstanding the above, nothing contained in the merger agreement gives The Doctors Company or Merger Sub, directly or indirectly, the right to control or direct ProAssurance’s or its subsidiaries’ operations prior to the effective time and nothing contained in the merger agreement gives ProAssurance, directly or indirectly, the right to control or direct The Doctors Company’s, Merger Sub’s or its subsidiaries’ operations prior to the effective time.

Subject to applicable law and certain other exceptions and limitations, from March 19, 2025 to the effective time, ProAssurance will, and will cause its subsidiaries, officers, directors, employees and representatives to, afford The Doctors Company and its representatives reasonable access, consistent with applicable law, during normal business hours to ProAssurance’s and its subsidiaries’ officers, employees, representatives and other

personnel and books and records, real property, offices and facilities and furnish to The Doctors Company all financial, operating and other data and information, in each case, as The Doctors Company shall from time to time reasonably request (but other than for any such matters that relate to the negotiation and execution of the merger agreement, including with respect to the consideration or valuation of the merger or any financial or strategic alternatives thereto, or that relate to any alternative proposal or superior proposal (but without limiting ProAssurance’s obligations under the merger agreement)), in each case, solely for purposes of, and to the extent reasonably necessary for, facilitating the consummation of the merger (including for integration planning).

From March 19, 2025 until the effective time or, if earlier, the valid termination of the merger agreement in accordance with its terms, ProAssurance will not, and will cause its subsidiaries not to and will direct its and their respective representatives not to, directly or indirectly:

Notwithstanding the foregoing, ProAssurance and the ProAssurance Board may:

From March 19, 2025 until the effective time or, if earlier, the valid termination of the merger agreement in accordance with its terms, except to the extent not otherwise permitted under the terms of the merger agreement, neither the ProAssurance Board nor any committee thereof shall make a change of recommendation.

Notwithstanding anything in the merger agreement to the contrary, prior to the time, but not after, the company requisite vote is obtained, if a bona fide, written acquisition proposal that did not result from a material breach of the non-solicitation provisions of the merger agreement is received by ProAssurance, and the ProAssurance Board determines in good faith, after consultation with its outside legal counsel and its financial advisor(s), that such acquisition proposal would, if consummated, constitute a superior proposal, the ProAssurance Board may, if the ProAssurance Board has determined in good faith after consultation with its outside legal counsel, that failure to take such action would be reasonably likely to be inconsistent with the directors’ fiduciary duties under applicable law, (a) effect a change of recommendation or (b) terminate the merger agreement pursuant to the terms thereof in order to enter into a definitive written agreement providing for such superior proposal; provided, however, that ProAssurance pays to The Doctors Company the termination payment of $52.6 million required to be paid pursuant to the merger agreement (as described below); provided further, that, prior to taking such actions described in clauses (a) or (b) above:

Notwithstanding anything in the merger agreement to the contrary, prior to the time, but not after, the company requisite vote is obtained, other than as provided in the provisions of the merger agreement related to acquisition proposals and change of recommendation, the ProAssurance Board may effect a change of recommendation if, (a) an intervening event (as defined below) has occurred, and (b) prior to taking such action, the ProAssurance Board has determined in good faith, after consultation with its outside legal counsel and its financial advisor(s), that failure to take such action in response to such intervening event would be reasonably likely to be inconsistent with the directors’ fiduciary duties under applicable law; provided, however, that prior to effecting such change of recommendation, (i) ProAssurance shall give notice to The Doctors Company four business days in advance, which notice shall include a reasonably detailed description of such intervening event, (ii) after giving such notice and prior to effecting a change of recommendation, ProAssurance shall, and shall direct its representatives to, negotiate in good faith with The Doctors Company (to the extent requested by The Doctors Company), to enable The Doctors Company to propose revisions to the terms of the merger agreement and (iii) at the end of the notice period, prior to and as a condition to effecting a change of recommendation, the ProAssurance Board shall take into account in good faith any changes to the terms of the merger agreement proposed in writing by The Doctors Company in response to the notice from ProAssurance and any other information offered by The Doctors Company in response to such notice, and shall have determined in good faith after consultation with its outside legal counsel and its financial advisor(s) that (A) such intervening event remains in effect and (B) the failure to effect a change of recommendation in response to such intervening event would be reasonably likely to be inconsistent with the directors’ fiduciary duties under applicable law if such changes proposed in writing by The Doctors Company (if any) were to be given effect.

ProAssurance agrees that immediately following March 19, 2024, it shall promptly (and in any event within 48 hours) give notice to The Doctors Company in writing of the receipt of any acquisition proposal or any inquiry, proposal, indication of interest or offer that would reasonably be expected to lead to, any acquisition proposal, which notice shall include a copy or a summary of the material terms and conditions of, and unredacted copies of any proposed agreements relating to such acquisition proposal (but not the identity of the person making such acquisition proposal or such inquiry, proposal, indication of interest or offer solely to the extent prohibited under the terms of any confidentiality agreement entered into prior to the date of the merger agreement), and shall thereafter keep The Doctors Company informed, on a reasonably current basis, of the status and material terms of any such acquisition proposal and inquiries, proposals, indications of interest or offers (including any material amendments or proposed material amendments thereto) and the status of any such discussions or negotiations and provide to The Doctors Company any nonpublic information concerning ProAssurance either prior to or promptly following being provided to any other person in connection therewith that was not previously provided to The Doctors Company. ProAssurance agrees that it shall not enter into any confidentiality agreement with any person subsequent to March 19, 2025 which prohibits ProAssurance from providing information to The Doctors Company as described above.

ProAssurance agreed that following March 19, 2025, it shall (a) immediately cease any solicitations, discussions or negotiations with any person (other than the parties to the merger agreement and their respective representatives) in connection with any acquisition proposal or any inquiry, proposals, indications of interests or offers that would reasonably be expected to lead to an acquisition proposal, in each case that existed as of March 19, 2025, (b) promptly request each person (other than the parties to the merger agreement and their respective representatives) that has prior to March 19, 2025 executed a confidentiality agreement in connection with its consideration of acquiring ProAssurance to return or destroy all confidential information furnished to

such person by or on behalf of it or any of its subsidiaries or its or their representatives in the 12 months prior to March 19, 2025 and (c) promptly terminate all physical and electronic data access previously granted to such persons. Any violation (other than an inadvertent or de minimis violation) of the restrictions set forth in the merger agreement by any director, executive officer or investment banker of ProAssurance or any director or officer of any of ProAssurance’s subsidiaries that is an employee of ProAssurance or any of its subsidiaries will be deemed to be a breach of the merger agreement by ProAssurance. Notwithstanding anything to the contrary in the merger agreement, but subject to ProAssurance’s compliance with the non-solicitation and change of recommendation provisions of the merger agreement, ProAssurance may grant a waiver, amendment or release under any confidentiality or standstill agreement (or any confidentiality or standstill provision of any agreement) to the extent necessary to allow for a confidential acquisition proposal to be made to ProAssurance or the ProAssurance Board so long as ProAssurance promptly notifies The Doctors Company thereof (but not the identity of such counterparty) after granting any such waiver, amendment or release.

The parties agreed that any violation (other than an inadvertent or de minimis violation) of the foregoing restrictions by any director, executive officer or investment banker of ProAssurance or any director or officer of any of the subsidiaries of ProAssurance that is an employee of ProAssurance or any of its subsidiaries shall be deemed to be a breach of the merger agreement by ProAssurance.

For purposes of the merger agreement, “acquisition proposal” means: any proposal or offer from any person or group of persons (other than The Doctors Company, Merger Sub or their respective affiliates) relating to, (a) any direct or indirect acquisition or purchase, in a single transaction or series of related transactions, by any person or group (as defined under Section 13 of the Exchange Act) of assets or one or more businesses that constitute 20% or more of the consolidated assets, net revenues or net income or fair market value (as determined in good faith by the ProAssurance Board) of the consolidated total assets (it being understood that total assets include equity securities of subsidiaries of ProAssurance) of ProAssurance and its subsidiaries, taken as a whole, (b) any direct or indirect acquisition or purchase resulting in any person or group (as defined under Section 13 of the Exchange Act) beneficially owning 20% or more of the total voting power of the equity securities of ProAssurance, (c) any tender offer or exchange offer that if consummated would result in any person or group (as defined under Section 13 of the Exchange Act) beneficially owning 20% or more of the total voting power of the equity securities of ProAssurance, or (d) any merger (including a reverse merger in which ProAssurance is the surviving corporation), reorganization, consolidation, share exchange, business combination, recapitalization, liquidation, dissolution or similar transaction involving ProAssurance (or any subsidiary of ProAssurance whose business constitutes 20% or more of the net revenues or net income or fair market value (as determined in good faith by the ProAssurance Board) of the consolidated total assets (it being understood that total assets include equity securities of subsidiaries of ProAssurance) of ProAssurance and its subsidiaries, taken as a whole); in each case of clauses (a) through (d), other than the transactions contemplated by the merger agreement; provided, that any proposal or offer to the extent related to any purchase of assets, properties or businesses to be divested or held separate pursuant to a regulatory remedy (as defined in the merger agreement) in accordance with the further actions and efforts provision of the merger agreement shall not be deemed an acquisition proposal.

For purposes of the merger agreement, “intervening event” means: any event, development, change, effect or occurrence (but specifically excluding any acquisition proposal or superior proposal) that is material to ProAssurance and its subsidiaries, taken as a whole, and that was not known by the ProAssurance board as of March 19, 2025 (or, if known, the consequences of which were not reasonably foreseeable by the ProAssurance Board as of March 19, 2025), which becomes known to ProAssurance or to the ProAssurance Board after March 19, 2025; provided that in no event shall any of the following be taken into account in determining whether an intervening event has occurred: (a) changes in the market price or trading volume of any securities of ProAssurance or its subsidiaries in and of itself (it being understood that the underlying causes of any such changes or developments may, if they are not otherwise excluded from the definition of “intervening event”, be taken into account in determining whether an intervening event has occurred), (b) any event, development, change, effect or occurrence relating to Parent, Merger Sub or any of their respective Affiliates, or (c) the fact, in and of itself, that ProAssurance exceeds any internal or analyst’s projection, guidance, budget, expectation, forecast or estimate for any period (it being understood that the underlying causes of any such matter may, if they are not otherwise excluded from the definition of “intervening event”, be taken into account in determining whether an intervening event has occurred).

For purposes of the merger agreement, “superior proposal” means: a bona fide, and written acquisition proposal (except that the references in the definition thereof to “20% or more” shall be deemed to be references to “50% or more”), that the ProAssurance Board, after consultation with its outside legal counsel and its financial advisor(s), in good faith determines (a) is reasonably likely to be consummated in accordance with its terms and (b) would, if consummated, result in a transaction that is more favorable from a financial point of view to the ProAssurance stockholders than the transactions contemplated hereby, in each case after taking into account all such factors and matters deemed relevant in good faith by the ProAssurance Board, including legal, financial (including the financing terms of any such proposal), regulatory and stockholder approval requirements, the sources, availability and terms of any financing, financing market conditions and the existence of any financing contingency, the likelihood of termination, the likely timing of closing, the identity of and any prior dealings with the person or persons making the proposal, timing or other aspects of such proposal and the transactions contemplated hereby and any other aspects considered relevant in good faith by the ProAssurance Board and after taking into account any changes to the terms of the merger agreement irrevocably offered in writing by The Doctors Company in response to such superior proposal pursuant to, and in accordance with, the merger agreement.

For purposes of the merger agreement, “change of recommendation” means any of the following actions by the ProAssurance Board: (a) failure to include the recommendation that the merger agreement be adopted by ProAssurance stockholders in this proxy statement (the “recommendation”), (b) withdrawing, modifying, amending, qualifying or changing the recommendation, (c) failing to recommend in a Solicitation/Recommendation Statement on Schedule 14D-9 against any acquisition proposal that is a tender offer or exchange offer subject to Regulation 14D promulgated under the Exchange Act for outstanding shares of ProAssurance common stock (other than by The Doctors Company or an affiliate of The Doctors Company), in each case, within 10 business days after the commencement thereof, it being understood and agreed that, for all purposes of the merger agreement, a communication by the ProAssurance Board to ProAssurance stockholders in accordance with Rule 14d-9(f) of the Exchange Act shall not, in and of itself, be deemed to constitute a change of recommendation (so long as any such disclosure does not include any statement that constitutes, and does not otherwise constitute, a change of recommendation) or (d) formally resolving to effect or publicly announce an intention or resolution to effect any of the foregoing.

For the avoidance of doubt, none of (a) the determination by the ProAssurance Board that an acquisition proposal constitutes a superior proposal, (b) the taking of any action by ProAssurance, the ProAssurance Board or any of its representatives permitted by the applicable provisions of the merger agreement relating to ProAssurance’s non-solicitation obligations (c) the delivery by ProAssurance to The Doctors Company of any notice contemplated by the applicable change of recommendation provisions, or (d) the public disclosure, in and of itself, of the items in clauses (a) through (c) if required by applicable law, will in and of itself constitute a change of recommendation.

For purposes of the merger agreement, “company requisite vote” means: the affirmative vote (in person or by proxy) of the holders of a majority of all of the outstanding shares of common stock entitled to vote thereon at the special meeting, or any adjournment or postponement thereof, to adopt the merger agreement.

ProAssurance, acting through the ProAssurance Board (or a committee thereof), shall, as promptly as reasonably practicable following the date on which ProAssurance is made aware that the SEC will not review this proxy statement or has no further comments on this proxy statement, take all action required under the DGCL, ProAssurance’s certificate of incorporation, ProAssurance’s bylaws and the applicable requirements of the NYSE to promptly and duly call, give notice of, convene and hold as promptly as reasonably practicable a special meeting of its stockholders for the purpose of (a) approving and adopting the merger agreement and (b) if and only if required by the DGCL, ProAssurance’s certificate of incorporation, ProAssurance’s bylaws, and the applicable requirements of the NYSE or otherwise mutually agreed, a vote upon other matters of the type customarily brought before a special meeting of stockholders in connection with the approval of a merger or the transaction contemplated by a merger agreement (including any adjournment or postponement thereof); except that ProAssurance may postpone, recess or adjourn such special meeting (and shall postpone, recess or adjourn if requested by The Doctors Company (but in such case ProAssurance shall not be required to postpone, recess or adjourn the special meeting to a date that is more than twenty business days after each such postponement, recess or adjournment)) (i) to the extent the Company has determined in good faith (after consultation with

outside counsel) that it is required by applicable law, including to allow additional time (up to ten business days after commencement of the applicable tender offer or exchange offer) for ProAssurance to file a Schedule 14D-9 in response to any acquisition proposal that is a tender offer or exchange offer subject to Regulation 14D promulgated under the Exchange Act for outstanding shares of ProAssurance common stock, (ii) to allow reasonable additional time to solicit additional proxies if reasonably requested by The Doctors Company to the extent ProAssurance reasonably believes necessary in order to obtain company requisite vote or to the extent ProAssurance reasonably believes necessary in order to obtain the company requisite vote, (iii) if as of the time for which the special meeting is originally scheduled (as set forth in the proxy statement) there are insufficient shares of ProAssurance common stock represented (either in person or by proxy) and voting to constitute a quorum necessary to conduct the business of the special meeting or (iv) to allow reasonable additional time for the filing and dissemination of any supplemental or amended disclosure which the ProAssurance Board has determined in good faith after consultation with outside counsel is necessary under applicable law or fiduciary duty and for such supplemental or amended disclosure to be disseminated and reviewed by ProAssurance stockholders prior to the special meeting.

ProAssurance, acting through the ProAssurance Board (or a committee thereof), is required to (a) include in the proxy statement the recommendation, and, subject to the consent of Goldman Sachs, the written opinion of Goldman Sachs and (b) use its reasonable best efforts to obtain the company requisite vote (it being understood that the ProAssurance Board will not be required to recommend in favor of the adoption of the merger agreement if a change of recommendation has been effected in accordance with the terms of the merger agreement). ProAssurance shall reasonably cooperate and keep The Doctors Company informed on a reasonably current basis regarding its solicitation efforts and voting results following dissemination of the definitive proxy statement.

For a period of at least twelve (12) months following the effective time (or, if earlier, the date on which the continuing employee terminates employment), (a) a base salary or base wage rate that is no less favorable than the base salary or base wage rate provided to such continuing employee immediately prior to the effective time, (b) a target annual cash bonus, and commissions opportunity, that, in each case, is substantially comparable to (i) for the remainder of the calendar year in which the closing date occurs, the target annual cash bonus, and commissions opportunity, provided to such continuing employee immediately prior to the effective time, and (ii) for the portion of the twelve (12) months that occurs in the calendar year following the calendar year in which the closing date occurs, the target annual cash bonus opportunity and commissions opportunity provided to similarly situated employees of The Doctors Company and its affiliates, (c) employee benefits (in each case, excluding defined benefit pension, deferred compensation, retiree medical, change in control, retention, and equity and equity-based compensation benefits) that are substantially comparable to either (i) the employee benefits provided to such continuing employee immediately prior to the effective time, or (ii) the employee benefits provided to similarly situated employees of The Doctors Company and its affiliates, and (d) a severance or termination arrangement that is no less favorable than the severance or termination arrangement provided to such continuing employee immediately prior to the effective time.

In addition, to the extent that The Doctors Company modifies any coverage or benefit plan in which continuing employees participate, The Doctors Company or any of its subsidiaries (including ProAssurance and any subsidiaries thereof) shall use reasonable best efforts to (a) waive or cause to be waived any pre-existing conditions, exclusions, limitations, actively-at-work requirements, and eligibility waiting periods under any group health plans of The Doctors Company or its affiliates to be waived with respect to continuing employees and their eligible dependents to the extent such pre-existing conditions, exclusions, limitations, actively-at-work requirements, and eligibility waiting periods were satisfied under a corresponding ProAssurance plan, (b) give each continuing employee credit for the plan year in which the effective time occurs towards applicable deductibles and annual out-of-pocket limits for medical expenses incurred under a corresponding ProAssurance plan prior to the effective time for which payment has been made and (c) to the extent that it would not result in a duplication of benefits and to the extent that such service was recognized under a similar ProAssurance Plan, give each continuing employee service credit for such continuing employee’s employment with ProAssurance for purposes of eligibility to participate and vesting credit (but excluding for vesting or benefit accrual purposes of any equity or equity-based compensation award made on or after the closing, and excluding benefit accrual for purposes of any defined benefit pension plan or retiree medical plan) under each applicable The Doctors Company benefit plan as if such service had been performed with The Doctors Company.

It is also anticipated that:

ProAssurance and The Doctors Company will (and, in the case of The Doctors Company, will cause each member of The Doctors Company Group to) use their respective reasonable best efforts to take, or cause to be taken, all actions and to do, or cause to be done, all things necessary, proper or advisable under applicable laws and regulations, including insurance laws, or pursuant to any contract or agreement to cause the conditions to the closing of the merger to be satisfied as promptly as reasonably practicable and advisable (and in any event no later than the end date) and to consummate the merger and the other transactions contemplated by the merger agreement as soon as reasonably practicable, including (a) preparing and filing as promptly as reasonably practicable all documentation to effect all necessary notices, reports and other filings, (b) obtaining as promptly as reasonably practicable (and in any event no later than the end date) all actions or nonactions, waivers, consents, registrations, expirations or terminations of waiting periods, approvals, permits and authorizations necessary or advisable to be obtained from any third party or any governmental entity in order to consummate the transactions contemplated by the merger agreement, (c) without limiting the obligations of The Doctors Company under the merger agreement, avoiding the entry of, effecting the dissolution of, and having vacated, modified, suspended, eliminated, lifted, reversed or overturned, any decree, decision, determination, order or judgment entered or issued or that becomes reasonably foreseeable to be entered or issued, that would, or would reasonably be expected to, prevent, restrain, enjoin, prohibit, make unlawful, restrict or delay the consummation of the contemplated transactions, so as to enable the parties to close the contemplated transactions as expeditiously as practicable (but in no event later than the end date), including the defending through litigation on the merits of any claim asserted in any court, agency or other proceeding by any person or entity (including any governmental entity) seeking to delay, restrain, prevent, enjoin or otherwise prohibit consummation of the transactions contemplated by the merger agreement, and (d) executing and delivering any additional instruments necessary to consummate the transactions contemplated by the merger agreement. In furtherance and not in limitation of the foregoing, (1) each party to the merger agreement agrees to file, or cause to be filed, all appropriate Notification and Report forms pursuant to the HSR Act with respect to the transactions contemplated by the merger agreement as promptly as reasonably practicable, (2) The Doctors Company shall, and shall use its

reasonable best efforts to cause each of its control persons under applicable law, if applicable, to file a “Form A” approval of acquisition of control with the insurance regulators as further discussed in the section of this proxy statement entitled “The Merger Proposal – Regulatory Approvals Required for the Merger” beginning on page 63 with respect to the acquisition of control of the company insurance subsidiaries (the “Form A Filings”), within twenty business days after March 19, 2025, (3) The Doctors Company shall file any pre-acquisition notifications on “Form E” or similar market share notifications (the “Form E Filings”) (a) in each jurisdiction in which a Form A filing is made or required to be made pursuant to the merger agreement, as further discussed in the section of this proxy statement entitled “The Merger Proposal – Regulatory Approvals Required for the Merger” beginning on page 63, concurrently with each such Form A and (b) in each other jurisdiction, within twenty business days after the date on which the last Form A filing described in clause (a) has been filed, but in no event later than forty business days after March 19, 2025, and in each case of this clause (b), only where required by applicable insurance laws, (4) The Doctors Company shall file a change-of-control application with Lloyd’s of London with respect to PRA Corporate Capital Ltd. within twenty business days after March 19, 2025, (5) ProAssurance shall file with the Cayman Islands Monetary Authority an application for approval for acquisition of control with respect to those subsidiaries of ProAssurance that are licensed entities in the Cayman Islands, within twenty business days after March 19, 2025, (6) The Doctors Company shall, and shall use its reasonable best efforts to cause each of its control persons under applicable law, if applicable, to file a FIN531 change-of-control filing with the Texas Department of Insurance pursuant to Tex. Ins. Code § 4001.253 with respect to those Subsidiaries of Company that are licensed as insurance agencies in the State of Texas, within twenty business days after March 19, 2025, (7) The Doctors Company or ProAssurance, as applicable, shall, and shall use its reasonable best efforts to cause each of their control persons under applicable law, if applicable, to, make any other necessary, proper, or advisable registrations, filings, and notices under non-U.S. insurance laws within twenty business days after March 19, 2025, and (8) each party to the merger agreement agrees to and to file, or cause to be filed, any filing (or, for jurisdictions where submission of a draft prior to formal notification is appropriate, a draft thereof) required under any other applicable antitrust, foreign investment, or insurance law with respect to the transactions contemplated hereby as promptly as practicable and in any event within twenty business days of March 19, 2025 (unless otherwise agreed to by the parties), and to supply as promptly as reasonably practicable any additional information and documentary material that may be requested pursuant to the HSR Act or such other antitrust, foreign investment or insurance law and to take any and all other actions necessary, proper or advisable to cause the expiration or termination of the applicable waiting periods under the HSR Act or such other antitrust, foreign investment or insurance law as promptly as reasonably practicable.

In connection with the efforts and obligations referenced in the paragraph above to obtain all requisite actions or nonactions, waivers, consents, registrations, expirations or terminations of waiting periods, approvals, permits and authorizations for the transactions contemplated by the merger agreement under the HSR Act or any other applicable antitrust, foreign investment or insurance law, each of The Doctors Company and Merger Sub, on the one hand, and ProAssurance and the Insurance Company Subsidiaries, on the other hand, will (a) consult and cooperate in all respects with each other in connection with any filing or submission and in connection with any investigation or other inquiry, including any proceeding initiated by a private party; (b) subject to applicable law, furnish to the other party as promptly as reasonably practicable all information required for any application or other filing to be made by the other party pursuant to any applicable law in connection with the transactions contemplated by the merger agreement; (c) promptly notify the other party of any substantive communication received by such party from, or given by such party to, the FTC, the Antitrust Division or any other U.S. or foreign governmental entity and of any substantive communication received or given in connection with any proceeding by a private party, in each case regarding any of the transactions contemplated by the merger agreement and, subject to applicable law, furnish the other party promptly with copies of all correspondence, filings and communications between them and the FTC, the DOJ or any other governmental entity with respect to the transactions contemplated by the merger agreement; (d) respond as promptly as reasonably practicable to any inquiries received from, and supply as promptly as reasonably practicable any additional information or documentation that may be requested by the FTC, the DOJ or by any other governmental entity in respect of such registrations, declarations and filings or such transactions contemplated by the merger agreement; and (e) permit the other party to review any substantive communication given by it to, and consult with each other in advance, and consider in good faith the other party’s reasonable comments in connection with, any filing, notice, application, submission, communication, meeting or conference with the FTC, the DOJ or any other governmental entity or, in connection with any proceeding by a private party, with any other person. No party to the merger agreement shall independently participate in any substantive meeting or communication with any

governmental entity in respect of any such filings, investigation or other inquiry relating to the above without giving the other parties sufficient prior notice of the meeting and, to the extent permitted by such governmental entity, the opportunity to attend or participate in such substantive meeting or communication. ProAssurance shall not commit to or agree with any governmental entity to stay, toll or extend any applicable waiting period, “pull-and-refile” pursuant to 16 C.F.R. 804.16 any filing made under the HSR Act, enter into a timing agreement, including any agreement to delay the consummation or not to consummate the transactions, or take any similar action, without the prior written consent (email to be sufficient) of The Doctors Company. The parties to the merger agreement acknowledge and agree that The Doctors Company shall control and direct (and ProAssurance shall cooperate with The Doctors Company in connection with) all strategy and decisions with respect to obtaining all approvals or other clearances under any applicable antitrust, foreign investment or insurance law, including all filings (including where to file and the timing of such filings) and any withdrawals and/or refiling thereof, strategies, processes, negotiation of settlements (if any), and related proceedings contemplated by the merger agreement, including for the avoidance of doubt the marketing or sale of any part of ProAssurance’s, The Doctors Company’s or any of their respective affiliates’ businesses or assets; provided, however, that The Doctors Company shall provide ProAssurance a reasonable opportunity to consult and consider such strategy and decisions and The Doctors Company will consider ProAssurance’s input and views with respect thereto in good faith (including with respect to any stay, toll or extension, “pull-and-refile”, entry into a timing agreement or any similar action described in the immediately preceding sentence).

The Doctors Company shall, and shall cause each member of the Doctors Company Group to, take any and all steps necessary, proper and advisable to (a) resolve, avoid, or eliminate impediments or objections, if any, that may be asserted with respect to the transactions contemplated by the merger agreement under any antitrust, foreign investment or insurance law or (b) avoid the entry of, effect the dissolution of, and have vacated, modified, suspended, eliminated, lifted, reversed or overturned, any decree, decision, determination, order or judgment entered or issued under any antitrust, foreign investment or insurance law, or that becomes reasonably foreseeable to be entered or issued, that would, or would reasonably be expected to, prevent, restrain, enjoin, prohibit, make unlawful, restrict or delay the consummation of the contemplated transactions, so as to enable the parties to the merger agreement to close the contemplated transactions as expeditiously as practicable (but in no event later than the end date), including (i) the defense through litigation on the merits of any claim under any antitrust, foreign investment or insurance law asserted in any court, agency or other proceeding by any person or entity (including any governmental entity) seeking to delay, restrain, prevent, enjoin or otherwise prohibit consummation of the transactions contemplated by the merger agreement and (ii) proposing, negotiating, committing to, agreeing to and effecting, by consent decree, hold separate orders or otherwise, the sale, lease, divesture, disposition, or license (or holding separate pending such disposition) of any assets, operations, rights, product lines, licenses, properties, products, rights, services or businesses of The Doctors Company or any member of The Doctors Company Group, or ProAssurance or its subsidiaries or any interest therein, (iii) otherwise taking or committing or agreeing to restrictions or actions that after the effective time would limit The Doctors Company’s, any member of The Doctors Company Group’s, or ProAssurance’s or its subsidiaries’ freedom of action or operations with respect to, or its or their ability to retain, any assets, operations, rights, product lines, licenses, properties, products, rights, services or businesses of The Doctors Company, The Doctors Company Group or ProAssurance or its subsidiaries or any interest or interests therein, including any rate freeze, rate decrease or restrictions to compete, or any capital contribution, capital support agreement, guarantee, keepwell or other similar capital maintenance undertaking (including to maintain a minimum risk-based capital level or rating), restrictions on dividends or distributions or (iv) agreeing to enter into, modify or terminate existing contractual relationships, contractual rights or contractual obligations, and promptly effecting the sale, lease, license, divestiture, disposal, and holding separate of assets, operations, rights, product lines, licenses, properties, products, rights, services or businesses of The Doctors Company, The Doctors Company Group, or ProAssurance or its subsidiaries or any interest or interests therein and the entry into agreements with, and submission to orders of, the relevant governmental entity giving effect thereto or to such restrictions or actions (such sale, lease, license, divestiture, disposal and holding separate or other action described in clause (ii), a “regulatory remedy”); provided that notwithstanding anything to the contrary set forth in the merger agreement, neither The Doctors Company nor any member of The Doctors Company Group shall be required to take or cause to be taken, do or cause to be done, propose, negotiate, commit to, suffer, become subject to, agree to or effect any regulatory remedy, or take any other action described in this paragraph (including as a result of any award, judgment, injunction or other order issued, entered or otherwise put into effect as a result of any claim asserted by an person) under any antitrust law, foreign investment law or insurance law, that would or would

reasonably be expected to have, individually or in the aggregate, a material adverse effect on the assets, business, results of operation or financial condition (x) ProAssurance and its subsidiaries, taken as a whole, or (y) The Doctors Company and its subsidiaries, taken as a whole (any such action, a “burdensome condition”). Prior to The Doctors Company being entitled to invoke a burdensome condition, the parties and their respective representatives shall promptly confer in good faith in order to (x) exchange and review their respective views and positions as to any burdensome condition or potential burdensome condition, (y) discuss in good faith potential approaches that would avoid such burdensome condition or mitigate its impact including with respect to further discussions with or analyses or other information to be provided to any U.S. or foreign governmental entity, and (z) negotiate in good faith with respect to any potential modification of the terms of the merger agreement or the other agreements or transactions contemplated hereby, on mutually acceptable terms and on an equitable basis, in a way that would substantially eliminate any such burdensome condition or sufficiently mitigate its adverse effect so that it would no longer constitute a burdensome condition hereunder. ProAssurance shall effectuate or agree to effectuate a regulatory remedy if requested to do so by The Doctors Company and shall not effectuate or agree to effectuate a regulatory remedy without the prior written consent of The Doctors Company.

Subject to the obligations set forth above, in the event that any administrative or judicial action or proceeding is instituted (or threatened to be instituted) by a governmental entity or private party challenging the merger or any other transaction contemplated by the merger agreement, or any other agreement contemplated by the merger agreement, (a) each party to the merger agreement shall, and The Doctors Company shall cause each member of The Doctors Company Group to, cooperate in all respects with each other and use its respective best efforts to contest and resist any such action or proceeding and to have vacated, modified, suspended, eliminated, lifted, reversed or overturned any decree, judgment, injunction or other order, whether temporary, preliminary or permanent, that is in effect and that prevents, restrains, enjoins, prohibits, makes unlawful, restricts or delays consummation of the transactions contemplated by the merger agreement and (b) The Doctors Company and Merger Sub or any other member of The Doctors Company Group shall, and The Doctors Company shall cause each member of The Doctors Company Group to defend, at their cost and expense, any action or actions, whether judicial or administrative, in connection with the transactions contemplated by the merger agreement. Notwithstanding the foregoing, neither of ProAssurance nor The Doctors Company shall be required to agree to any term or take any action (in each case, including any regulatory remedy) in connection with its foregoing obligations in the merger agreement that is not conditioned upon consummation of the merger. Notwithstanding the foregoing, except as set forth in the provisions of the merger agreement relating to closing conditions, obtaining any approval or consent from any Person pursuant to the merger agreement shall not be a condition to the obligations of the parties to consummate the transactions contemplated by the merger agreement.

Except as required or permitted by the merger agreement or as required by applicable law, neither The Doctors Company nor Merger Sub nor any member of The Doctors Company Group shall, and The Doctors Company shall cause each member of The Doctors Company Group not to, (a) acquire or enter into a definitive agreement agreeing to acquire, including by merging with or into or consolidating with, or by purchasing a portion of the assets of or equity in, or by any other manner, any business or any person, corporation, partnership, association or other business organization or division thereof, or otherwise acquire or agree to acquire any assets or equity interests, or otherwise acquire or agree to acquire any assets, properties or equity interests, if the entering into of a definitive agreement relating to, or the consummation of such acquisition, merger or consolidation or purchase would reasonably be expected to or (b) take any other action (except for any action giving rise to (i) any rate filing which includes an actuarial memorandum signed by a qualified actuary or policy form filing or (ii) any filing required to be made under applicable insurance laws in connection with any ordinary course transaction between The Doctors Company and any of its affiliates, other than Merger Sub (or among The Doctors Company’s affiliates (other than Merger Sub)) that The Doctors Company would, based on the information and circumstances actually known by The Doctors Company at the time such action is taken, reasonably expect to: (A) impose any material delay in the obtaining of, or materially increase the risk of not obtaining, any consents of any governmental entity or private party necessary to consummate the transactions contemplated by the merger agreement or the expiration or termination of any applicable waiting period; (B) increase the risk of any governmental entity or private party seeking or entering an order prohibiting the consummation of the transactions contemplated by the merger agreement; (C) increase the risk of not being able to remove any such order on appeal or otherwise; or (D) materially delay or prevent the consummation of the transactions contemplated by the merger agreement.

Notwithstanding the foregoing, commercially or competitively sensitive information and materials of a party to the merger agreement will be provided to the other party on an outside-counsel-only basis, while, to the extent feasible, making a version in which the commercially or competitively sensitive information has been redacted available to the other party. Materials provided to the other party or its counsel pursuant to the preceding sentence may be redacted to remove references (a) concerning the valuation of ProAssurance, (b) as necessary to comply with contractual arrangements, or (c) as necessary to address reasonable attorney-client privilege or confidentiality concerns; provided that, if ProAssurance in good faith believes that material not covered by the preceding clauses (a through c) nevertheless warrants redaction from information and materials it provides to The Doctors Company’s counsel on an outside-counsel-only basis, The Doctors Company will consider in good faith a request for consent to such redaction, such consent not to be unreasonably withheld.

From and after the effective time through the sixth anniversary of the date on which the effective time occurs, The Doctors Company shall cause the surviving corporation to indemnify and hold harmless each present (as of the effective time) and former director and officer of ProAssurance or any of its subsidiaries (in each case, when acting in such capacity), against any costs or expenses (including reasonable attorneys’ fees), judgments, fines, losses, claims, damages, liabilities or awards paid in settlement incurred in connection with any actual or threatened claim, action, suit, proceeding or investigation, whether civil, criminal, administrative or investigative and whether formal or informal, arising out of, relating to or in connection with the fact that such person is or was a director or officer of ProAssurance or any of its subsidiaries or serving in such capacity at the request thereof or any acts or omissions occurring or alleged to occur prior to the effective time in such person’s capacity as a director or officer of ProAssurance or any of its subsidiaries or serving in such capacity at the request thereof, whether asserted or claimed prior to, at or after the effective time, to the fullest extent that ProAssurance would have been permitted under its certificate of incorporation or bylaws in effect as of immediately prior to the effective time and under Delaware law. The Doctors Company shall cause the surviving corporation to advance expenses (including reasonable legal fees and expenses) incurred in the defense of any proceeding, including any expenses incurred in enforcing such person’s rights under the indemnification provisions of the merger agreement, and such indemnified party is entitled to receive such advancement to the fullest extent permitted under the certificate of incorporation, the bylaws, or equivalent organizational documents of any applicable subsidiary, in each case, as in effect as of immediately prior to the effective time, and under applicable law; provided that the person to whom expenses are advanced provides an undertaking to repay such advances if it is determined by a final and non-appealable judgment of a court of competent jurisdiction that such person is not legally entitled to indemnification under applicable law. In the event of any such proceeding (a) neither The Doctors Company nor the surviving corporation will settle, compromise or consent to the entry of any judgment in any proceeding in which indemnification could be sought by such indemnified party hereunder, unless such settlement, compromise or consent includes an unconditional release of such indemnified party from all liability arising out of such proceeding or such indemnified party otherwise consents and (b) the surviving corporation will reasonably cooperate in the defense of any such matter. In the event any proceeding is brought against any indemnified party and in which indemnification could be sought by such indemnified party, (i) the surviving corporation will have the right to control the defense thereof after the effective time, (ii) each indemnified party will be entitled to retain his or her own counsel, whether or not the surviving corporation will elect to control the defense of any such proceeding, but in each case, subject to the terms of the merger agreement, (iii) the surviving corporation will pay all reasonable fees and expenses of any counsel retained by an indemnified party promptly after statements therefor are received, whether or not the surviving corporation elects to control the defense of any such proceeding and (iv) no indemnified party will be liable for any settlement effected without his or her prior express written consent. Any indemnified party wishing to claim indemnification under the merger agreement, upon learning of any proceeding, will promptly notify The Doctors Company thereof; but the failure of such indemnified party to so notify will not relieve The Doctors Company or the surviving corporation of any liability it may have to such indemnified party except to the extent such failure materially prejudices The Doctors Company, the surviving corporation or any of their respective affiliates. The provisions in the surviving corporation’s certificate of incorporation and bylaws with respect to indemnification, advancement of expenses and exculpation of former or present directors and officers will be no less favorable to such directors and officers than such provisions contained in ProAssurance’s certificate of incorporation and bylaws in effect as of March 19, 2025, which provisions will not be amended, repealed or otherwise modified for a period of six years after the effective time in any manner that would adversely affect the rights thereunder of any such individuals.

ProAssurance will purchase from insurance carriers with comparable credit ratings, no later than the effective time, a six-year prepaid “tail policy” providing at least the same coverage and amounts containing terms and conditions that are no less advantageous in the aggregate to the insured than the current policies of directors’ and officers’ liability insurance and fiduciary liability insurance maintained by ProAssurance and its subsidiaries with respect to claims arising from facts or events that occurred at or before the effective time, including the transactions contemplated by the merger agreement, and from insurance carriers having the same or better credit rating as ProAssurance’s directors’ and officers’ liability insurance carrier as of March 19, 2025; provided, however, that after the effective time, The Doctors Company and the surviving corporation will not be required to pay in the aggregate for such coverage under each such policy more than 300% of the last annual premium paid by ProAssurance prior to March 19, 2025 in respect of the coverage required to be obtained pursuant thereto under each such policy, but in such case shall purchase as much coverage as reasonably practicable for such amount. In the event ProAssurance elects to purchase such a “tail policy,” the surviving corporation will (and The Doctors Company will cause the surviving corporation to) maintain such “tail policy” in full force and effect for at least six years from the effective time and continue to honor their respective obligations thereunder. If ProAssurance elects not to purchase such a “tail policy,” then The Doctors Company shall maintain, or shall cause the surviving corporation to maintain, at no expense to the beneficiaries, in effect for at least six years from the effective time the current policies of the directors’ and officers’ liability insurance and fiduciary liability insurance maintained by ProAssurance (provided that The Doctors Company or the surviving corporation may substitute therefor policies of at least the same coverage containing terms and conditions which are not less advantageous to any beneficiary thereof) with respect to matters existing or occurring at or prior to the effective time and from insurance carriers having the same or better credit rating as ProAssurance’s directors’ and officers’ liability insurance carrier as of March 19, 2025; provided, however, that after the effective time, The Doctors Company and the surviving corporation will not be required to pay in the aggregate for such coverage under each such policy more than 300% of the last annual premium paid by ProAssurance prior to March 19, 2025 in respect of the coverage required to be obtained pursuant thereto under each such policy, but in such case shall obtain a policy with the greatest coverage available for a cost not exceeding such amount from insurance carriers having the same or better credit rating as ProAssurance’s directors” and officers’ liability insurance carrier as of March 19, 2025. The Doctors Company agrees to honor and perform under, and to cause the surviving corporation to honor and perform under, all indemnification agreements entered into by ProAssurance or any of its subsidiaries with any indemnified party.

The merger agreement contains additional agreements among ProAssurance, The Doctors Company and Merger Sub relating to, among other matters:

The respective obligations of each of ProAssurance, The Doctors Company and Merger Sub to consummate the merger are subject to the satisfaction (or written waiver by ProAssurance and The Doctors Company (to the extent permitted by applicable law)) at or prior to the closing date of the following conditions:

The respective obligations of The Doctors Company and Merger Sub to effect the merger are also subject to the satisfaction (or written waiver by The Doctors Company (to the extent permitted by applicable law)) at or prior to the closing date of the following conditions:

The obligation of ProAssurance to effect the merger is also subject to the satisfaction (or written waiver by ProAssurance (to the extent permitted by applicable law)) at or prior to the closing date of the following conditions:

The merger agreement may be terminated and the merger may be abandoned at any time prior to the effective time, whether before or after the company requisite vote is obtained (except as otherwise expressly noted), as follows:

by written notice from ProAssurance:

by written notice from The Doctors Company if:

ProAssurance must pay to The Doctors Company a termination fee of $52.6 million in the event that:

The Doctors Company must pay to ProAssurance a termination fee of $52.6 million in the event that:

If either ProAssurance or The Doctors Company fail to pay any termination fee described above, as applicable, within the specified time period, ProAssurance or The Doctors Company, as applicable, will be required to reimburse the other party’s reasonable out-of-pocket costs and expenses incurred in connection with any suit taken to collect payment of such amounts in which the other party prevails. Neither ProAssurance or The Doctors Company will be required to pay the applicable termination fee on more than one occasion.

If the merger agreement is terminated in accordance with its terms, the merger agreement will become void and there shall be no liability or obligation on the part of any party thereto, except as provided by certain provisions of the merger agreement, including but not limited to those related to confidentiality, publicity, the payment of any termination fee as described above, payment of costs and expenses as described below and certain other obligations which will survive the termination in accordance with the terms and conditions of the merger agreement; provided that the termination of the merger agreement will not relieve any party thereto of any liability for damages resulting from such party’s willful breach prior to the termination of the merger agreement by any party thereto. In circumstances in which the termination fee is paid by The Doctors Company or ProAssurance, such termination fee will be the sole and exclusive monetary remedy of the other party, except for breaches of the confidentiality and publicity provisions of the merger agreement.

Except as otherwise provided in the merger agreement, each party will bear its own expenses in connection with the merger agreement and the transactions contemplated by the merger agreement. Filing fees and other expenses incurred in connection with obtaining any consents or making any filings under any antitrust laws or insurance laws will be borne by The Doctors Company. Expenses incurred in connection with the filing, printing and mailing of this proxy statement will be shared equally by The Doctors Company and ProAssurance.

Subject to the provisions of applicable law, at any time before the effective time, the parties to the merger agreement may modify or amend the merger agreement only by written agreement, executed and delivered by duly authorized officers of the respective parties.

At any time before the effective time, any party to the merger agreement may (a) extend the time for the performance of any of the obligations or other acts of the other parties, (b) waive any inaccuracies in the representations and warranties contained in the merger agreement or in any document delivered pursuant thereto and (c) subject to the requirements of applicable law, waive compliance with any of the covenants, agreements or conditions contained in the merger agreement. Any such extension or waiver will only be valid if set forth in an

instrument in writing signed by the party or parties to be bound thereby and specifically referencing the merger agreement. For the purposes relating to this provision, The Doctors Company and Merger Sub will be treated as a single party.

The parties to the merger agreement are entitled (in addition to any other remedy to which they may be entitled in law or equity) to an injunction, specific performance or other equitable relief to prevent breaches or threatened breaches of the merger agreement and to enforce specifically the terms and provisions of the merger agreement.

The merger agreement and any disputes relating thereto shall be governed by, and construed in accordance with, the laws of the State of Delaware (without giving effect to choice of law or conflict of law principles thereof or of any other jurisdiction that would cause the application of any laws of any jurisdiction other than the State of Delaware).

Each of the parties to the merger agreement irrevocably (a) consents to submit itself to the personal jurisdiction of the Delaware Court of Chancery and any state appellate court therefrom within the State of Delaware (unless the Delaware Court of Chancery declines to accept jurisdiction over a particular matter, in which case, in any Delaware state or federal court within the State of Delaware), in connection with any matter based upon or arising out of the merger agreement or any of the transactions contemplated by the merger agreement or the actions of The Doctors Company, Merger Sub or ProAssurance in the negotiation, administration, performance and enforcement thereof and (b) agrees that it will not bring any action relating to the merger agreement or any of the transactions contemplated by the merger agreement in any court other than the courts of the State of Delaware.

In accordance with Section 14A of the Exchange Act, ProAssurance is providing its stockholders with the opportunity to cast a non-binding, advisory vote on the compensation that will be paid or may become payable to the named executive officers of ProAssurance in connection with the merger, the value of which is set forth in the table entitled “Golden Parachute Compensation” in the section of this proxy statement entitled “The Merger Proposal (Proposal 1)—Interests of ProAssurance’s Executive Officers and Directors in the Merger” beginning on page 57. This proposal, commonly known as “say-on-golden parachutes” is referred to in this proxy statement as the named executive officer merger-related compensation proposal. As required by Section 14A of the Exchange Act, ProAssurance is asking its stockholders to vote on the adoption of the following resolution:

“RESOLVED, that the compensation that may be paid or become payable to ProAssurance’s named executive officers in connection with the merger, as disclosed under “The Merger Proposal (Proposal 1)—Interests of ProAssurance’s Executive Officers and Directors in the Merger—Potential Merger-Related Payments to Named Executive Officers,” including the table, associated footnotes and narrative discussion, is hereby APPROVED.”

The vote on the named executive officer merger-related compensation proposal is a vote separate and apart from the vote on the merger proposal. Accordingly, you may vote to approve the merger proposal and vote not to approve the named executive officer merger-related compensation proposal, and vice versa. Because the vote to approve the named executive officer merger-related compensation proposal is only advisory in nature, it will not be binding on ProAssurance, The Doctors Company or the surviving corporation. Accordingly, because ProAssurance is contractually obligated to pay such merger-related compensation, the compensation will be paid or payable, subject only to the conditions applicable thereto, if the merger proposal is approved, regardless of the outcome of the advisory vote.

Assuming a quorum is present, approval of the named executive officer merger-related compensation proposal (on a non-binding basis) requires the affirmative vote of the holders of a majority in voting power of the outstanding shares of ProAssurance common stock present in person or represented by proxy at the special meeting and entitled to vote thereon. Abstentions will have the same effect as a vote “AGAINST” the named executive officer merger-related compensation proposal. Broker non-votes, if any, will have no effect on the outcome of the named executive officer merger-related compensation proposal. If you sign and return a proxy and do not indicate how you wish to vote on the named executive officer merger-related compensation proposal, your shares will be voted in favor of the named executive officer merger-related compensation proposal.

The ProAssurance Board unanimously recommends that ProAssurance stockholders vote “FOR” the named executive officer merger-related compensation proposal.

ProAssurance stockholders are being asked to approve a proposal that will give ProAssurance the authority to adjourn the special meeting from time to time, as necessary, as determined in good faith by the ProAssurance Board, including for the purpose of soliciting additional proxies in favor of the merger proposal if there are insufficient votes at the time of the special meeting to approve the merger proposal. If a quorum is not present, the presiding officer at the special meeting may adjourn the special meeting from time to time until a quorum is present. If the adjournment is for more than 30 days, or if, after the adjournment, a new record date is fixed for the adjourned special meeting, a notice of the adjourned special meeting will be given to each stockholder of record entitled to vote at the meeting. In addition, the special meeting could be postponed before it commences, subject to the terms of the merger agreement. If the special meeting is adjourned or postponed, stockholders who have already submitted their proxies will be able to revoke them at any time prior to the final vote on the proposals.

Assuming a quorum is present, approval of the adjournment proposal requires the vote of the holders of a majority of the outstanding shares of ProAssurance common stock present in person or represented by proxy at the special meeting. Abstentions will have the same effect as a vote “AGAINST” the adjournment proposal. Broker non-votes, if any, will have no effect on the outcome of the adjournment proposal. If you sign and return a proxy and do not indicate how you wish to vote on the adjournment proposal, your shares will be voted in favor of the adjournment proposal. ProAssurance does not intend to call a vote on this proposal if the merger proposal has been approved at the special meeting.

The ProAssurance Board unanimously recommends that ProAssurance stockholders vote “FOR” the adjournment proposal.

ProAssurance common stock trades on the NYSE under the symbol “PRA”. The following table shows the high and low closing sales price of ProAssurance common stock for ProAssurance’s second fiscal quarter of 2025 (through May 13, 2025, the latest practicable date before the printing of this proxy statement) and each of ProAssurance’s preceding fiscal quarters in 2025, 2024, 2023 and 2022.