Rate Sheet Prospectus Supplement Dated September 1, 2021 to the Prospectus dated September 1, 2021
for MassMutual EnvisionSM Variable Annuity Issued by Massachusetts Mutual Life Insurance Company
Massachusetts Mutual Variable Annuity Separate Account 4

This Rate Sheet Prospectus Supplement (“Rate Sheet”) should be read carefully and retained with the Prospectus dated September 1, 2021 for the MassMutual EnvisionSM Variable Annuity. You may obtain a current Prospectus at www.MassMutual.com/Envision or by calling (800) 272-2216, sending an email request to ANNfax@MassMutual.com, or writing to MassMutual, P.O. Box 9067, Springfield, MA 01102-9067.

We are issuing this Rate Sheet to update the following information regarding the MassMutual RetirePaySM Guaranteed Lifetime Withdrawal Benefit (RetirePay):

•

Withdrawal Rates,

​

•

Lifetime Guarantee Rates,

​

•

RetirePay Charges, and

​

•

Investment Allocation Restrictions

​

(collectively, referred to as the “RetirePay Terms.”)

The RetirePay Terms included in this Rate Sheet are effective for applications submitted on or after September 1, 2021 until a new Rate Sheet is issued that replaces and supersedes this Rate Sheet.

This Rate Sheet replaces and supersedes any previously issued Rate Sheet. This Rate Sheet has no specified end date. This Rate Sheet must be used in conjunction with an effective MassMutual EnvisionSM Variable Annuity Prospectus. For complete information about RetirePay, see the “Additional Benefits — MassMutual RetirePaySM” section in the MassMutual EnvisionSM Variable Annuity Prospectus.

If we change the RetirePay Terms, we will issue a new Rate Sheet. In the event we issue a new Rate Sheet, we will provide at least 10 business days’ notice of the effective date of the superseding Rate Sheet.

Rate Sheet Eligibility Conditions

Certain Rate Sheet eligibility conditions apply when we have issued a superseding Rate Sheet after you apply for your contract and prior to your issue date.

In order for the RetirePay Terms in this Rate Sheet to apply to your Contract, your necessary application information, including any applicable transfer form(s), must be submitted to an order entry system utilized to issue the Contract (“application submit date”) on or after September 1, 2021 and prior to the effective date of the superseding Rate Sheet. For purposes of this process, the application submit date is also defined to include the date the application is signed if a paper application is necessary.

Application Information Submitted with a Purchase Payment

In addition to the submission of your necessary application information, we also require payment of at least the minimum initial Purchase Payment and the application information to be in Good Order within 10 business days after the application submit date.

If these Rate Sheet Eligibility Conditions are met, and the Contract is issued, the RetirePay Terms in this Rate Sheet will apply, unless a beneficial superseding rate sheet applies, as described under “Rate Sheet Comparison Process.”

If these Rate Sheet Eligibility Conditions are not met, we will cancel the application and return your Purchase Payment.

Application Information Submitted without a Purchase Payment

If you plan to pay the initial Purchase Payment with proceeds from an IRS Section 1035 exchange or direct transfer, your transfer form(s) and application information must be in Good Order within 10 Business Days after the application submit date. In addition, the initial Purchase Payment necessary to issue the Contract must be received within 90 calendar days after the application submit date.

If these Rate Sheet Eligibility Conditions are met, and the Contract is issued, the RetirePay Terms in this Rate Sheet will apply, unless a beneficial superseding rate sheet applies, as described under “Rate Sheet Comparison Process.”

If these Rate Sheet Eligibility Conditions are not met, we will inform you and request instructions regarding whether to issue the Contract with the RetirePay Terms in effect under the superseding Rate Sheet or cancel the application.

If you have not provided us with the requested instructions within 2 business days after we have received your Purchase Payment, we will return your Purchase Payment to the original source.

The requirement to have the necessary application information in Good Order within 10 Business Days for application information received with a Purchase Payment or without a Purchase Payment includes completion of the broker-dealer suitability review.

Rate Sheet Comparison Process

Subject to satisfying the Rate Sheet Eligibility Conditions established in this Rate Sheet, if after your application submit date and prior to your Issue Date, a subsequent Rate Sheet is issued with only beneficial changes to the RetirePay Terms, the subsequent Rate Sheet will apply. The changes will be considered to be beneficial unless any of the following occurs:

•

Withdrawal Rates and/or Lifetime Guarantee Rates have decreased,

​

•

RetirePay Charges have increased, or

​

•

Investment Allocation Restrictions have changed (unless the sole change to the Investment Allocation Restrictions is the addition of available investment options).

​

For example, if the RetirePay Charges have increased, you will receive the RetirePay Terms included in the Rate Sheet in effect on your application submit date even if the Withdrawal Rates and/or Lifetime Guarantee Rates have increased in the subsequent Rate Sheet.

You should not purchase RetirePay without first obtaining the applicable Rate Sheet. To obtain a current Rate Sheet:

•

Contact your financial advisor

​

•

Contact us toll-free at (800) 272-2216

​

•

Go to www.MassMutual.com/Envision

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On the Guaranteed Lifetime Withdrawal Date, we will determine the Withdrawal Rate and the Lifetime Guarantee Rate based on the number of full Contract Years from the RetirePay Issue Date and the Age of the Covered Person (or the youngest Covered Person for a Joint Life Version). The Withdrawal Rate applies when your Contract Value is greater than zero. The Lifetime Guarantee Rate applies when your Contract Value is zero. Once the contract is issued, the Withdrawal Rates and the Lifetime Guarantee Rates applicable to your Contract below will not change for the life of your Contract.

SINGLE LIFE WITHDRAWAL RATES:

JOINT LIFE WITHDRAWAL RATES:

SINGLE LIFE LIFETIME GUARANTEE RATES:

JOINT LIFE LIFETIME GUARANTEE RATES:

CURRENT RETIREPAY CHARGES

The current RetirePay Charges applicable to your Contract are as follows:

The amount that is deducted from your Contract Value is equal to the RetirePay Charge multiplied by the Benefit Base. We may increase the RetirePay Charges at any time, with prior notice, but the charges will never exceed the maximum RetirePay Charge. The maximum charge can be found in the “RetirePay Charge” section of the current MassMutual Envision prospectus.

INVESTMENT ALLOCATION RESTRICTIONS

While RetirePay is in effect, your investment allocations are restricted.

You must either be invested 100% in one of the MML Asset Allocation Sub-Accounts or invested 100% in the Custom Allocation Program.

MML Asset Allocation Sub-Accounts:

MML Conservative Allocation
MML Moderate Allocation
MML Balanced Allocation
MML American Funds Core Allocation
MML Growth Allocation
MML Blend
MML iShares® 80/20 Allocation
MML iShares® 60/40 Allocation

Custom Allocation Program:

Multiple Sub-Accounts can be selected within each category. The total allocation for all Sub-Accounts within each category must be between the minimum and maximum allocation. The Contract Value in the Custom Allocation Program will be rebalanced based on your elected frequency. If no election is made, rebalancing will occur quarterly during each calendar year.

If a requested change in your allocations or a transfer of any portion of your contract value does not comply with these investment restrictions, you will be required to terminate your RetirePay by written request before the allocation change or transfer can be processed. We reserve the right, upon thirty calendar days advance notice to you, to change the investment restrictions. If we change the investment restrictions, you must change your allocations to comply within thirty calendar days of the restrictions becoming effective, or we will terminate your RetirePay.

If you have any questions regarding this Rate Sheet, please contact us toll free at (800) 272-2216. Please keep this Rate Sheet for future reference.

MassMutual EnvisionSM Variable Annuity

Issued by Massachusetts Mutual Life Insurance Company
Massachusetts Mutual Variable Annuity Separate Account 4

This prospectus describes an individual variable deferred annuity contract with flexible premium payments (“Contract”) offered by Massachusetts Mutual Life Insurance Company (“MassMutual,” “Company,” “we,” “us,” or “our”). The Contract may not be available in all states. The Contract offers a choice of features and benefits. You, as the owner of the Contract (“you,” “Owner”), determine which ones may be appropriate for you, based on your financial circumstances and objectives. The fees and charges that you pay are based on the features and benefits that you select.

You may accumulate value on a tax-deferred basis under your Contract by allocating your money to a fixed account for dollar cost averaging (“DCA Fixed Account”) and/or one or more variable investment divisions (“Sub-Accounts”) of Massachusetts Mutual Variable Annuity Separate Account 4 (“Separate Account”). Each Sub-Account, in turn, invests in one of the investment entities (“Funds”) listed in “Appendix A – Funds Available Under the Contract.” The investment choices available to you are restricted if MassMutual RetirePaySM is in effect. See “Additional Benefits – MassMutual RetirePaySM” for more information. You bear the entire investment risk for all amounts you allocate to a Sub-Account.

To learn more about the Contract, you can obtain a copy of the Statement of Additional Information (SAI), dated September 1, 2021. The SAI is incorporated by reference into this prospectus. The prospectus and SAI are parts of the registration statement that we filed with the Securities and Exchange Commission (SEC). The SEC maintains a website (www.sec.gov) that contains the registration statement, material incorporated by reference, and other information regarding companies that file electronically with the SEC.

For a free copy of the SAI, or for general inquiries, call our Service Center at (800) 272-2216, send an email request to ANNfax@MassMutual.com, or write to our Service Center using the following address: MassMutual, P.O. Box 9067, Springfield, MA 01102-9067.

The Contract:

IF YOU ARE A NEW INVESTOR IN THE CONTRACT, YOU MAY CANCEL YOUR CONTRACT WITHIN 10 DAYS OF
RECEIVING IT WITHOUT PAYING FEES OR PENALTIES.

In some states this cancellation period may be longer. Upon cancellation, you will receive either a full refund of the amount you paid with your application or your total Contract Value. You should review the prospectus, or consult with your investment professional, for additional information about the specific cancellation terms that apply.

Additional information about certain investment products, including variable annuities, has been prepared by the Securities and Exchange Commission staff and is available at Investor.gov.

This prospectus is not an offer to sell the Contract in any jurisdiction where it is illegal to offer the Contract nor is it an offer to sell the Contract to anyone to whom it is illegal to offer the Contract.

Please read this prospectus before investing. You should keep it for future reference. It contains important information about the MassMutual EnvisionSM Variable Annuity.

Effective September 1, 2021

Table of Contents

​	Glossary	​	​	​	​	1	​	​
​	Important Information You Should Consider About the MassMutual EnvisionSM Variable Annuity Contract	​	​	​	​	4	​	​
​	Fees and Expenses	​	​	​	​	4	​	​
​	Risks	​	​	​	​	6	​	​
​	Restrictions	​	​	​	​	6	​	​
​	Taxes	​	​	​	​	7	​	​
​	Conflicts of Interest	​	​	​	​	8	​	​
​	Overview of the Contract	​	​	​	​	9	​	​
​	Additional Information about Fees	​	​	​	​	11	​	​
​	Principal Risks of Investing in the Contract	​	​	​	​	14	​	​
​	General Information about Massachusetts Mutual Life Insurance Company, the Separate Account and the Investment Choices	​	​	​	​	15	​	​
​	The Company	​	​	​	​	15	​	​
​	Financial Condition of the Company	​	​	​	​	15	​	​
​	The Separate Account	​	​	​	​	16	​	​
​	The Funds	​	​	​	​	16	​	​
​	Compensation We Receive from Funds, Advisers and Sub-Advisers	​	​	​	​	17	​	​
​	Voting Rights	​	​	​	​	18	​	​
​	Fixed Account For Dollar Cost Averaging (DCA Fixed Account)	​	​	​	​	18	​	​
​	Charges and Deductions	​	​	​	​	20	​	​
​	Insurance Charges	​	​	​	​	20	​	​
​	Annual Contract Maintenance Charge	​	​	​	​	20	​	​
​	Contingent Deferred Sales Charge (CDSC)	​	​	​	​	21	​	​
​	Premium Taxes	​	​	​	​	22	​	​
​	Income Taxes	​	​	​	​	22	​	​
​	Fund Expenses	​	​	​	​	22	​	​
​	RetirePay Charges	​	​	​	​	22	​	​
​	Ownership	​	​	​	​	23	​	​
​	Owner	​	​	​	​	23	​	​
​	Joint Owner	​	​	​	​	23	​	​
​	Annuitant	​	​	​	​	23	​	​
​	Beneficiary	​	​	​	​	24	​	​
​	Purchasing a Contract	​	​	​	​	24	​	​
​	Contract Delay	​	​	​	​	24	​	​
​	Purchase Payments	​	​	​	​	25	​	​
​	Allocation of Purchase Payments	​	​	​	​	25	​	​
​	Contract Value	​	​	​	​	26	​	​

​	Right to Cancel Your Contract	​	​	​	​	27	​	​
​	Sending Requests in Good Order	​	​	​	​	27	​	​
​	Transfers and Transfer Programs	​	​	​	​	27	​	​
​	General Overview	​	​	​	​	27	​	​
​	Transfers During the Accumulation Phase	​	​	​	​	28	​	​
​	Transfers During the Annuity Phase	​	​	​	​	28	​	​
​	Transfer Programs	​	​	​	​	28	​	​
​	Limits on Frequent Trading and Market Timing Activity	​	​	​	​	29	​	​
​	The Annuity Phase	​	​	​	​	30	​	​
​	Benefits Available Under the Contract	​	​	​	​	35	​	​
​	Death Benefit	​	​	​	​	37	​	​
​	Death of Owner During the Accumulation Phase	​	​	​	​	37	​	​
​	Death Benefit Amount During the Accumulation Phase	​	​	​	​	38	​	​
​	Death Benefit Payment Options During the Accumulation Phase	​	​	​	​	39	​	​
​	Beneficiary IRA	​	​	​	​	40	​	​
​	Death of Owner During the Annuity Phase	​	​	​	​	41	​	​
​	Death of Annuitant	​	​	​	​	41	​	​
​	Additional Benefits	​	​	​	​	41	​	​
​	Terminal Illness Withdrawal Benefit	​	​	​	​	41	​	​
​	Nursing Home and Hospital Withdrawal Benefit	​	​	​	​	42	​	​
​	MassMutual RetirePaySM	​	​	​	​	42	​	​
​	Withdrawals	​	​	​	​	51	​	​
​	Taxes	​	​	​	​	53	​	​
​	Distribution	​	​	​	​	61	​	​
​	Other Information	​	​	​	​	62	​	​
​	Collateral Assignment	​	​	​	​	62	​	​
​	Registered Representative Transaction Authority	​	​	​	​	63	​	​
​	Unclaimed Property	​	​	​	​	63	​	​
​	Anti-Money Laundering	​	​	​	​	63	​	​
​	Payments We Make	​	​	​	​	63	​	​
​	Changes to the Contract	​	​	​	​	63	​	​
​	Special Arrangements	​	​	​	​	64	​	​
​	Termination of the Contract	​	​	​	​	64	​	​
​	Reservation of Rights	​	​	​	​	64	​	​
​	Computer System, Cybersecurity, and Service Disruption Risks	​	​	​	​	64	​	​
​	Legal Proceedings	​	​	​	​	65	​	​

​	Our Financial Statements	​	​	​	​	65	​	​
​	Appendix A – Funds Available Under the Contract	​	​	​	​	66	​	​
​	Appendix B – Contingent Deferred Sales Charge (CDSC) Example	​	​	​	​	72	​	​
​	Appendix C – Free Withdrawal Amount Examples	​	​	​	​	73	​	​
​	Appendix D – Return of Purchase Payment Death Benefit Examples	​	​	​	​	75	​	​

​	Appendix E – Commuted Value Withdrawal Example	​	​	​	​	77	​	​
​	Appendix F – RetirePay Examples	​	​	​	​	78	​	​
​	Appendix G – State Variations of Certain Contract Features	​	​	​	​	87	​	​
​	Appendix H – Superseded Rate Sheet Prospectus Supplement Information	​	​	​	​	88	​	​

Glossary

Accumulation Phase. Your Contract’s Accumulation Phase begins on the date we issue your Contract and ends on the Annuity Date, the date you withdraw all of your Contract Value, or the date your Contract terminates.

Accumulation Unit. A unit of measure used to determine your value in a Sub-Account during the Accumulation Phase.

Age. The attained age of any Owner or that of any Annuitant or Beneficiary, as applicable, at his or her last birthday, except with respect to fixed annuity payout rates. If the Contract is owned by a non-natural person (e.g., a corporation, trust or other entity), then Age shall mean the attained age of any Annuitant at his/her last birthday, except with respect to fixed annuity payout rates. If you have elected RetirePay, this definition of Age also applies to the Covered Person. For the purpose of calculating Annuity Payments, Age will be determined based on each Annuitant’s nearest birthday on the Annuity Date. For example, Age 65 is considered the period of time between age 64 years, 6 months and one day, and age 65 years and 6 months.

Annual Lifetime Benefit Amount. The Annual Lifetime Benefit Amount is the maximum amount that may be withdrawn in the current Contract Year without being considered an Excess Withdrawal while RetirePay is in effect.

Annuitant. The person(s) on whose life Annuity Payments are based, with the exception of the period certain Annuity Option. The term Annuitant shall also include the joint Annuitant, if any. The Annuitant has no rights to the Contract.

Annuity Date. The date Annuity Payments begin. The latest date that the Contract Value may be applied to provide Annuity Payments is set forth in “The Annuity Phase – Latest Permitted Annuity Date.”

Annuity Options. Options available for Annuity Payments.

Annuity Payments. A series of payments that will be made pursuant to the Annuity Option you elect.

Annuity Phase. The period which begins on the Annuity Date and ends with the last Annuity Payment.

Beneficiary. The person(s) or entity(ies) that you designated to receive the death benefit provided by the Contract.

Benefit Base. The Benefit Base is the amount we use to determine your Annual Lifetime Benefit Amount while RetirePay is in effect.

Business Day.  Every day the New York Stock Exchange or its successors (“NYSE”) is open for trading. Our Business Day ends at the Close of Business.

Close of Business. The time on a Business Day when the NYSE ends regular trading, usually at 4:00 p.m. Eastern Time.

Company. Massachusetts Mutual Life Insurance Company, which may also be referred to in this prospectus as “we”, “us”, or “our”.

Contingent Deferred Sales Charge (CDSC). A charge that may be assessed against each Purchase Payment you withdraw from the Contract. (In some states referred to as a surrender charge.)

Contract. The MassMutual EnvisionSM Variable Annuity; an individual variable deferred annuity contract with flexible premium payments.

Contract Anniversary. An anniversary of the Issue Date of the Contract.

Contract Schedule Date. The effective date of any schedule to the Contract. A Contract schedule bearing the latest Contract Schedule Date will supersede all previous Contract schedules.

Contract Value. The sum of your value in the Sub-Accounts and in the Fixed Account(s) during the Accumulation Phase.

Contract Withdrawal Value. The Contract Value less any applicable Premium Taxes not previously deducted; less any applicable annual contract maintenance charge; less any applicable CDSC; less any Purchase Payments credited to the Contract that have not yet cleared the bank, until they clear the bank.

Contract Year. The first Contract Year is the annual period which begins on the Issue Date and ends on the last calendar day before the first Contract Anniversary. Subsequent Contract Years begin on subsequent Contract Anniversaries.

Covered Person. The person(s) whose life is used to determine the duration of the Annual Lifetime Benefit Amount provided under RetirePay.

Excess Withdrawal. Under the optional RetirePay feature, an Excess Withdrawal is:

(a)

prior to the Guaranteed Lifetime Withdrawal Date, any withdrawal, including the Free Withdrawal Amount, and

​

(b)

on or after the Guaranteed Lifetime Withdrawal Date, any portion of a withdrawal (including CDSCs applicable to the withdrawal) that causes the cumulative withdrawals to exceed the Annual Lifetime Benefit Amount in that Contract Year and any withdrawal that occurs after the cumulative withdrawals exceed the Annual Lifetime Benefit Amount in that Contract Year, unless the withdrawal is taken as a part of the Company’s Systematic Withdrawal Program established for the payment of RMDs, under which the RMD is calculated by the Company for the current calendar year based solely on the fair market value of the Contract as defined in IRC Section 401(a)(9) and no other withdrawals are taken within the Contract Year.

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Fixed Account For Dollar Cost Averaging. An investment option within the General Account which may be selected during the Accumulation Phase and also is referred to as the “DCA Fixed Account”. The DCA Fixed Account is a fixed account from which assets are systematically transferred to any Sub-Account(s) you select.

Fixed Annuity Payments. Annuity Payments made during the Annuity Phase which we guarantee as to the dollar amount of each Annuity Payment.

Free Withdrawal Amount. The Free Withdrawal Amount is an amount of your Purchase Payment(s) that you may withdraw that is not subject to the CDSC.

Fund. An investment entity into which the assets of a Sub-Account will be invested.

General Account. The Company’s general investment account, which supports the Company’s annuity and insurance obligations. The General Account’s assets include all of our assets, with the exception of the Separate Account and the Company’s other segregated asset accounts.

Good Order. An instruction or transaction request that we receive at our Service Center generally is considered in “Good Order” if:

(1)

we receive it within the time limits, if any, prescribed in this prospectus for a particular request or transaction;

​

(2)

it includes all information necessary for us to execute the request or transaction; and

​

(3)

it is signed by you or persons authorized to provide instruction to engage in the request or transaction.

​

A request or transaction may be rejected or delayed if not in Good Order. Good Order generally means the actual receipt by our Service Center of the instructions related to the request or transaction in writing (or, when permitted, by telephone, fax or Internet) along with all forms, information and supporting legal documentation we require to effect the request or transaction. This information generally includes to the extent applicable: the completed application or instruction form; your Contract number; the transaction amount (in dollars or percentage terms); the names and allocation to and/or from the Sub-Accounts affected by the request or transaction; the signatures of all owners; if necessary, Social Security Number or Tax Identification number; tax certification; and any other information or supporting documentation we may require including consents, certifications and guarantees. Instructions must be complete and sufficiently clear so that we do not need to exercise any discretion to follow such instructions. We will not accept instructions that require additional requirements or burdens not provided for within the Contract. With respect to Purchase Payments, Good Order also generally includes receipt by us of sufficient funds to affect the purchase. We may, in our sole discretion, determine whether any particular request or transaction is in Good Order, and we reserve the right to change or waive any Good Order requirements at any time. If you have any questions you may contact our Service Center before submitting the form or request. See “Sending Requests in Good Order” for more information.

Guaranteed Lifetime Withdrawal Date. The date on which the Company guarantees the Withdrawal Rate under the benefit, and on which you may begin receiving payments of the Annual Lifetime Benefit Amount while RetirePay is in effect. This date must be selected by the Owner and cannot be prior to the youngest Covered Person attaining age 591∕2.

Issue Date. The date the Contract became effective, as shown in the Contract schedule.

Lifetime Guarantee Rate. The Lifetime Guarantee Rate is a percentage we multiply by the Benefit Base to determine the Annual Lifetime Benefit Amount once the Contract enters the Settlement Phase while RetirePay is in effect.

Non-Business Day. Any day when the NYSE is not open for trading.

Non-Qualified Contract. Your Contract is referred to as a Non-Qualified Contract if you purchase the Contract as an individual, and not under a qualified plan such as an Individual Retirement Annuity (IRA) or a Roth IRA.

Owner. The person(s) or entity (“you” and “your”) entitled to the ownership rights stated in the Contract. The term Owner also shall include the joint Owner, if any.

Premium Tax. A tax imposed on us by certain states and other jurisdictions when a Purchase Payment is made, when Annuity Payments begin, or when Contract Value is withdrawn.

Purchase Payment. Any amount paid to us by you or on your behalf with respect to the Contract during the Accumulation Phase. Purchase Payments may not be added after the Annuity Date. Restrictions will apply if RetirePay is in effect.

Qualified Contract. Your Contract is referred to as a Qualified Contract if it is purchased under a qualified retirement plan (qualified plan) such as an Individual Retirement Annuity (IRA) or a Roth IRA.

Rate Sheet Prospectus Supplement. A periodic supplement to the information contained in this prospectus which sets forth the Withdrawal Rates, Lifetime Guarantee Rates, current RetirePay Charges, and investment allocation restrictions under RetirePay. See “Benefits Available Under The Contract – MassMutual RetirePaySM” in this prospectus.

Required Minimum Distribution (RMD). A Required Minimum Distribution (RMD) is a minimum amount the federal tax law requires to be withdrawn from certain Qualified Contracts each year. RMDs are generally required to begin by the required beginning date specified in IRC Section 401(a)(9).

RetirePay Charge. The RetirePay Charge is an amount that is deducted from your Contract Value equal to the current RetirePay Charge multiplied by the Benefit Base on such day (after taking into account any other transactions processed on such day) while RetirePay is in effect.

RetirePay. An optional benefit for an additional charge. If you elect RetirePay, we will permit you to receive the Annual Lifetime Benefit Amount for the life of the Covered Person, even if your Contract Value is zero and subject to the terms and conditions described in the section of this prospectus concerning the benefit while RetirePay is in effect.

Settlement Phase. When the Contract Value is reduced to zero after the Guaranteed Lifetime Withdrawal Date due to a withdrawal that is not an Excess Withdrawal or due to the application of any charges against Contract Value while RetirePay is in effect.

Separate Account. The account that holds the assets underlying the Contract that are not allocated to the Fixed Account(s). The assets of the Separate Account are kept separate from the assets of the General Account and the Company’s other separate accounts.

Service Center.  MassMutual, P.O. Box 9067, Springfield, MA 01102-9067, (800) 272-2216, www.MassMutual.com.

Sub-Account(s). Separate Account assets are divided into Sub-Accounts, which are listed on the Contract schedule. The assets of each Sub-Account will be invested in the shares of a single Fund.

Withdrawal Rate. The Withdrawal Rate is a percentage we multiply by the Benefit Base to determine the Annual Lifetime Benefit Amount prior to the Settlement Phase while RetirePay is in effect.

Written Notice. A written or electronic communication or instruction we send to you. Any notice that we send to you will be sent to your last known address, unless you request otherwise via Written Request. You must promptly provide us with notice of any change of your address.

Written Request. A written communication or instruction you send to us in Good Order. We may consent to receiving requests electronically or by telephone at our Service Center.

Important Information You Should Consider About the MassMutual EnvisionSM Variable Annuity Contract

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(1)

Represents an estimate of the mortality and expense risk charge and administrative charge (charged as a percentage of Contract Value) and an estimate of the annual contract maintenance charge (a fixed dollar amount that may be waived for certain Contract Value amounts) collected during the Contract Year that are attributable to the Contract divided by an estimate of the total average net assets that are attributable to the Contract.

​

(2)

As a percentage of Fund assets.

​

(3)

The fee is the annual fee for RetirePay, and is a percentage of the Benefit Base. See “Benefits Available Under the Contract – MassMutual RetirePaySM” and the applicable Rate Sheet Prospectus Supplement for the current RetirePay Charges.

​

Overview of the Contract

What is the Contract, and what is it designed to do? The MassMutual EnvisionSM Variable Annuity is designed to enable you to accumulate assets through investments in one or more of the variable investment divisions (Sub-Accounts) of the Massachusetts Mutual Variable Annuity Separate Account 4 (Separate Account) and the DCA Fixed Account. The Contract can supplement your retirement income by providing a stream of income during the Annuity Phase. Before you begin receiving annuity payments, the Contract also provides a death benefit for your designated beneficiaries. The Contract may be appropriate if you have a long term investment horizon. It is not intended for people who need to take early withdrawals or who intend to engage in frequent trading among the Sub-Accounts of the Separate Account.

How do I accumulate assets in the Contract and receive income from the Contract? The Contract has two phases 1) the Accumulation Phase and 2) the Annuity Phase.

Accumulation Phase

During the Accumulation Phase, subject to certain restrictions, including restrictions associated with RetirePay, you may apply Purchase Payments to the Contract and allocate the Purchase Payments:

◦

among the Sub-Accounts of the Separate Account, each of which invests in a mutual fund (Fund), with each Fund having its own investment strategy, investment adviser, expense ratio and returns, and

​

◦

the DCA Fixed Account for a scheduled term of six or twelve months. Assets allocated to the DCA Fixed Account are credited with a fixed rate of interest and are systematically transferred to Sub-Accounts that you select.

​

A list of the Funds in which you may invest is provided at the back of this prospectus. See “Appendix A – Funds Available Under the Contract.”

Annuity Phase

During the Annuity Phase, you may receive annuity payments under the Contract by applying your Contract Value to a payment option.

◦

Depending on the payment option you select, payments may continue for the life of one or two annuitants or for a specified period between 10 and 30 years. The payments will remain the same throughout the Annuity Phase, unless you elect either of the Joint and 2/3 Survivor annuity options, which reduce payments on the death of the first annuitant.

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When you elect to receive Annuity Payments, the Contract Value is applied to an Annuity Option and you may no longer be able to withdraw money at will from the Contract. If you apply your Contract Value to an Annuity Option, the Accumulation Phase will end and the death benefit will terminate.

RetirePay will terminate if you apply your Contract Value to an Annuity Option other than one of the Annuity Options under RetirePay. Upon the death of the last surviving Annuitant on or after the Annuity Date, the death benefit, if any, is as specified in the Annuity Option elected. Upon the death of the last surviving Annuitant during the Annuity Phase, any remaining payment under the elected Annuity Option will be paid to the Beneficiary. See “The Annuity Phase.”

What are the primary features and options that the MassMutual EnvisionSM Variable Annuity offers? 

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Accessing your money. During the Accumulation Phase, you may make a partial or full withdrawal of your Contract Value by submitting our partial withdrawal form or full withdrawal form in Good Order to our Service Center. You may also submit the requests by other means that we authorize, such as e-mail, telephone or fax. Contact our Service Center for details.

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All withdrawals are subject to the limitations described in the prospectus. Withdrawal rights during the Annuity Phase will depend on the Annuity Option selected.

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Tax treatment. You may transfer Contract Value among Sub-Accounts without tax implications, and earnings (if any) on your investments are generally tax-deferred. You are generally taxed only when (1) you make a partial or full withdrawal; (2) you receive an Annuity Payment under the Contract; or (3) upon payment of the death benefit.

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Death Benefit. Your Contract includes a death benefit that will pay your designated beneficiaries the greater of (1) the Contract Value when we receive due proof of death and election of a payment method; or (2) an amount based on your Purchase Payments adjusted for withdrawals.

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RetirePay Guaranteed Lifetime Withdrawal Benefit. For an additional charge, you may elect RetirePay, under which we guarantee that you may take a certain amount of withdrawals annually for life, so long as you adhere to the requirements of the benefit (e.g., allocating your Contract Value only to the Sub-Accounts that are prescribed for this benefit). For complete information on RetirePay, including charges and limitations, see “Benefits Under The Contract – MassMutual RetirePaySM.”

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Additional Benefits and Services. We make certain additional services available under the Contract at no additional charge:

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The Separate Account Dollar Cost Averaging Program allows you to transfer a set amount from a Sub-account to any other Sub-account on a regular schedule. The Automatic Rebalancing Program automatically rebalances your Contract Value among your selected Sub-Accounts in order to restore your allocation to the original level. You may participate only in one Program at a time, and you may not participate in either Program if any Contract Value is allocated to the DCA Fixed Account.

The Systematic Withdrawal Program allows you to set up automatic periodic withdrawals from your Contract Value. We will take any withdrawal under this Program proportionally from your Contract Value in your selected investment choices.

The Terminal Illness Withdrawal Benefit allows you to withdraw all or a portion of your Contract Value without incurring a Contingent Deferred Sales Charge (CDSC) if we receive a Written Request in Good Order that certain conditions are met.

The Nursing Home and Hospital Withdrawal Benefit allows you to withdraw all or a portion of your Contract Value without incurring a CDSC if we receive a Written Request in Good Order that you (or the Annuitant, if the Owner of the Contract is not a natural person) have been admitted to a licensed nursing care facility or an accredited hospital and certain other conditions are satisfied. See “Additional Benefits” for a full explanation of the required conditions.

The Terminal Illness Withdrawal Benefit and the Nursing Home and Hospital Withdrawal Benefit are not available in all states.

The prospectus and Statement of Additional Information (SAI) describe all material terms and features of your Contract. Certain non-material provisions of your Contract may be different than the general description in the prospectus and the SAI, and certain riders may not be available because of legal requirements in your state. Any such state variations will be included in your Contract or in riders or endorsements attached to your Contract. See your Contract for specific variations. Also see “Appendix G – State Variations of Certain Contract Features.”

Additional Information about Fees

The following tables describe the fees and expenses you will pay when buying, owning, and surrendering or making withdrawals from the Contract. Please refer to your Contract specifications page for information about the specific fees you will pay each year based on the options you have elected.

The first table describes the fees and expenses that you will pay at the time that you buy the Contract, surrender or make withdrawals from the Contract, or transfer Contract Value between investment options. State premium taxes may also be deducted.

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(1)

The CDSC percentage charge is based on the “age” of the Purchase Payment(s) being withdrawn (i.e., the number of full years from application of the Purchase Payment).

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The CDSC percentages are 7% (for first three years), 6% (for 4th year), 5% (for 5th year), 4% (for 6th year), 3% (for 7th year), and 0% (for 8th year and later).

See “Charges and Deductions – Contingent Deferred Sales Charge” for more information.

The next table describes the fees and expenses you will pay each year during the time you own the Contract, not including underlying Fund fees and expenses. If you choose to purchase an optional benefit, you will pay additional charges, as shown below.

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(1)

Currently, we waive this charge if, when we would make the deduction, your Contract Value is $100,000 or more. We assess the charge on each Contract Anniversary and when you make a full withdrawal.

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(2)

The Base Contract Charge is the sum of the mortality and expense risk charge and the administrative charge. The current and maximum mortality and expense risk charge is 1.15% annually and the current administrative charge is 0.15% annually. These charges are a percentage of average account value in the Separate Account on an annualized basis.

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(3)

We deduct the quarterly portion of this annualized charge from your Contract Value on a quarterly basis in arrears.

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Total Annual Fund Operating Expenses

The next item shows the minimum and maximum total operating expenses charged by the Funds that you may pay periodically during the time that you own the Contract. A complete list of Funds available under the Contract, including their annual expenses, may be found in Appendix A.

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(1)

The Fund expenses used to prepare this table were provided to us by the Funds. We have not independently verified such information provided to us by Funds that are not affiliated with us.

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The information above describes the fees and expenses you pay related to the Contract. For information on compensation we may receive from the Funds and their advisers and sub-advisers, see “General Information about Massachusetts Mutual Life Insurance Company, the Separate Account and the Investment Choices – Compensation We Receive from Funds, Advisers and Sub-Advisers.” For information on compensation we pay to broker-dealers selling the Contract, see “Distribution.”

Examples

These examples are intended to help you compare the cost of investing in the Contract with the cost of investing in other variable annuity contracts. These costs include Owner transaction expenses, annual Contract expenses, and Fund fees and expenses.

The first example assumes that you invest $100,000 in the Contract for the time periods indicated. The example also assumes that your investment has a 5% return each year and assumes the most expensive combination of annual Fund expenses and RetirePay is in effect for an additional charge. Although your actual costs may be higher or lower, based on these assumptions, your costs would be:

The next example assumes that you invest $100,000 in the Contract for the time periods indicated. The example also assumes that your investment has a 5% return each year and assumes the least expensive combination of annual Fund expenses and assumes RetirePay is not in effect. Although your actual costs may be higher or lower, based on these assumptions, your costs would be:

Principal Risks of Investing in the Contract

There are risks associated with investing in the Contract. The value of your investment and any returns will depend on the performance of the Funds you select. Each Fund may have its own unique risks. You bear the risk of any decline in your Contract Value resulting from the poor performance of the Funds you have selected. You can lose money in a variable annuity, including potential loss of your original investment.

Variable annuities are not a short-term investment vehicle. The CDSC may apply for a number of years, so that the Contract should only be purchased for the long-term. Under some circumstances, you may receive less than the sum of your Purchase Payments. In addition, full or partial withdrawals will be subject to income tax to the extent that they consist of earnings and an additional 10% federal income tax may apply to the taxable portion if taken before age 591∕2. Accordingly, you should carefully consider your income and liquidity needs before purchasing a Contract. Additional information about these risks appear in “Important Information You Should Consider About the MassMutual EnvisionSM Variable Annuity Contract” page 4, in “Withdrawals” page 51 and “Taxes” page 53.

Investment Risk. You bear the risk of any decline in the Contract Value caused by the performance of the Funds held by the Subaccounts. Those Funds could decline in value very significantly, and there is a risk of loss of your entire amount invested. The risk of loss varies with each Fund. This risk could have a significant negative impact on the value under RetirePay. The investment risks are described in the prospectuses for the Funds.

Investment Restrictions – Opportunity Risks. RetirePay restricts your choice of available Funds. These restrictions are intended to protect us financially, in that they reduce the likelihood that we will have to pay guaranteed benefits under RetirePay from our own assets. These restrictions could result in an opportunity cost – in the form of Funds that you did not invest in that ultimately might generate superior investment performance. Thus, you should consider these restrictions when deciding whether to elect RetirePay.

Risk Associated With Election of RetirePay. RetirePay includes several requirements and limitations that must be adhered to in order to preserve and maximize the guarantees we offer under the benefit. If you fail to adhere to these requirements, that may diminish the value of the benefit and even possibly cause termination of the benefit. In addition, it is possible that you will pay fees for RetirePay without fully realizing the guarantees available under the benefit. For example, if your Contract terminates before the Settlement Phase, you will not have maximized the benefits provided under RetirePay.

Insurance Company Insolvency. It is possible that we could experience financial difficulty in the future and even become insolvent, and therefore unable to provide all of the guarantees and benefits that we promise that exceed the value of the assets in the Separate Account. Similarly, our experiencing financial difficulty could interfere with our ability to fulfill our obligations under the DCA Fixed Account.

Tax Consequences. Withdrawals are generally taxable to the extent of any earnings in the Contract, and prior to age 591∕2 an additional 10% federal income tax may apply to the taxable portion. In addition, even if the Contract is held for years before any withdrawal is made, withdrawals are taxable as ordinary income rather than capital gains.

Cybersecurity and Certain Business Continuity Risks

Our operations support complex transactions and are highly dependent on the proper functioning of information technology and communication systems. Any failure of or gap in the systems and processes necessary to support complex transactions and avoid systems failure, fraud, information security failures, processing errors, cyber intrusion, loss of data and breaches of regulation may lead to a materially adverse effect on our results of operations and corporate reputation. In addition, we must commit significant resources to maintain and enhance our existing systems in order to keep pace with applicable regulatory requirements, industry standards and customer preferences. If we fail to maintain secure and well-functioning information systems, we may not be able to rely on information for product pricing, compliance obligations, risk management and underwriting decisions. In addition, we cannot assure investors or consumers that interruptions, failures or breaches in security of these processes and systems will not occur, or if they do occur, that they can be timely detected and remediated. The occurrence of any of these events may have a materially adverse effect on our businesses, results of operations and financial condition.

For additional detail regarding cybersecurity and related risks, please see “Other Information – Computer System, Cybersecurity, and Service Disruption Risks” in this prospectus.

General Information about Massachusetts Mutual Life Insurance Company, the Separate Account and the Investment Choices

The Company

MassMutual is organized as a mutual life insurance company. MassMutual’s home office is located at 1295 State Street, Springfield, Massachusetts 01111-0001.

MassMutual and its domestic life insurance subsidiaries provide individual and group life insurance, disability insurance, individual and group annuities and guaranteed interest contracts to individual and institutional customers in all 50 states of the U.S., the District of Columbia and Puerto Rico. Products and services are offered primarily through the Company’s distribution channels: MassMutual Financial Advisors, Digital Direct to Consumer and Business to Business, Institutional Solutions and Workplace Solutions.

The assets of our General Account support our insurance and annuity obligations and are subject to our general liabilities from our business operations and to claims by our creditors. You should be aware that, unlike the Separate Account, the Company’s General Account is not segregated or insulated from the claims of the Company’s creditors. In addition, because of exemptive and exclusionary provisions, the General Account, unlike the Separate Account, has not been registered under the Securities Act of 1933 (1933 Act) or the Investment Company Act of 1940 (1940 Act). Because of this, the General Account is generally not subject to the provisions of the 1933 Act or the 1940 Act. However, disclosures regarding the General Account are subject to certain generally applicable provisions of the federal securities laws that require complete and accurate statements in prospectuses.

Financial Condition of the Company

We use General Account assets for many purposes, including to pay death benefits, Annuity Payments, withdrawals and transfers from Fixed Account investment choices and to pay amounts we provide to you through any elected additional feature that are in excess of your Contract Value allocated to the Separate Account. Any amounts that we may be obligated to pay under the Contract in excess of Contract Value are subject to our financial strength and claims-paying ability and our long-term ability to make such payments. The assets of the Separate Account, however, are also available to cover the liabilities of our General Account, but only to the extent they exceed our liabilities under the Contract and other contracts we issue that are funded by the Separate Account.

We issue other types of insurance policies and financial products as well, and we pay our obligations under those products from our assets in the General Account.

As an insurance company, we are required by state insurance regulation to hold a specified amount of reserves in order to meet the contractual obligations of our General Account to our insurance policies and financial products. We monitor our reserves so that we hold sufficient amounts to cover actual or expected contract and claims payments. In addition, we hedge our investments in our General Account and may require that purchasers of certain of our variable insurance products allocate Purchase Payments and Contract Value according to specified investment requirements. Even with these safeguards in place, there are risks to purchasing any insurance product and there is no guarantee that we will always be able to meet our claims-paying obligations.

State insurance regulators also require insurance companies to maintain a minimum amount of capital, which acts as a cushion if the insurer suffers a financial setback because of the inherent risks in the insurer’s operations. These risks include losses that we may incur as the result of defaults on the payment of interest or principal on our General Account assets – e.g., bonds, mortgages, general real estate investments, and stocks – as well as the loss in market value of these investments.

We continue to evaluate our investment portfolio to mitigate market risk and actively manage the investment in that portfolio.

The MassMutual financial information in the SAI includes a more detailed discussion of the risks inherent in our General Account assets. We encourage both existing and prospective Owners to read and understand our financial statements.

The Separate Account

We established Massachusetts Mutual Variable Annuity Separate Account 4 (Separate Account) as a separate account under Massachusetts law on July 9, 1997. The Separate Account is registered with the SEC as a unit investment trust under the 1940 Act.

The Separate Account holds the assets that underlie the Contracts (and certain other contracts that we issue), except any assets allocated to our General Account. We keep the Separate Account assets separate from the assets of our General Account and other separate accounts. The Separate Account is divided into Sub-Accounts, each of which invests exclusively in a single Fund.

We own the assets of the Separate Account. We credit gains to, or charge losses against, the Separate Account, whether or not realized, without regard to the performance of other investment accounts. The Separate Account’s assets may not be used to pay any of our liabilities other than those arising from the Contracts (or other contracts that we issue and that are funded by the Separate Account). If the Separate Account’s assets exceed the required reserves and other liabilities, we may transfer the excess to our General Account. The obligations of the Separate Account are not our generalized obligations and will be satisfied solely by the assets of the Separate Account. We are obligated to pay all amounts promised to investors under the Contract.

We reserve the right, subject to compliance with applicable federal securities laws and regulations and any other federal or state law, to make certain changes to the structure and operation of the Separate Account, including, among other things:

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eliminate, combine or add Sub-Accounts;

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combine the Separate Account or any Sub-Account(s) with one or more different separate account(s) or Sub-Account(s);

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close existing Sub-Accounts to allocations of new Purchase Payments and Contract Value by current or new Owners;

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transfer assets of the Separate Account or any Sub-Account that we may determine to be associated with the class of contracts in which the Contract belongs to another separate account or Sub-Account;

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operate the Separate Account as a management investment company under the 1940 Act, or as any other form permitted by law;

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add or remove Funds or Fund classes in which the Sub-Accounts invest; and

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substitute a new Fund for a Fund in which a Sub-Account currently invests (new or substitute Funds may have different fees and expenses).

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In the event we exercise these rights, we will provide Written Notice to the Owner(s).

The Funds

Information about each Fund, including its name, type or investment objective, investment adviser(s) expenses, and performance is available in an appendix to this Prospectus. See “Appendix A – Funds Available Under the Contract”. There is no assurance that any of the Funds will achieve their stated objectives.

These Funds are only available to insurance company separate accounts and qualified retirement plans, are not available for purchase directly by the general public, and are not the same as other mutual fund portfolios with very similar or nearly identical names and investment goals and policies that are sold directly to the public. While a Fund may have many similarities to these other publicly available mutual funds, you should not expect the investment results of the Fund to be the same as the investment results of those publicly available mutual funds. We do not guarantee or make any representation that the investment results of the Funds will be comparable to the investment results of any other mutual fund, even a mutual fund with the same investment adviser or manager.

The prospectus for each Fund contains more detailed information about the Fund. You may obtain copies of the Fund prospectuses by contacting our Service Center. If you received a summary prospectus for a Fund, please follow the directions on the first page of the Summary Prospectus to obtain a copy of the full Fund prospectus.

Conflicts of Interest

The Funds available with the Contract may also be available to registered separate accounts offering variable annuity and variable life products of other affiliated and unaffiliated insurance companies, as well as to the Separate Account and

other separate accounts of MassMutual. Although we do not anticipate any disadvantages to this, it is possible that a material conflict may arise between the interests of the Separate Account and one or more of the other separate accounts participating in the Funds. A conflict may occur, for example, as a result of a change in law affecting the operations of variable life and variable annuity separate accounts, differences in the voting instructions of the Owners and payees and those of other insurance companies, or some other reason. In the event of a conflict of interest, we will take steps necessary to protect Owners and payees, including withdrawing the Separate Account from participation in the Funds involved in the conflict or substituting shares of other funds.

We do not recommend or endorse any particular Fund, and we do not provide investment advice. You are responsible for choosing the Funds, and the amounts allocated to each, that are appropriate for your own individual circumstances and your investment goals, financial situation, and risk tolerance. Because many Funds have similar names, be sure to state or write the full name of the Sub-Account when providing your allocation instructions to ensure that your allocation instructions are in Good Order. You bear the risk of any decline in your Contract Value resulting from the performance of the Funds that you choose.

Selection of Funds

When we select the Funds offered through the Contract, we consider various factors, including, but not limited to, asset class coverage, the strength of the adviser’s or sub-adviser’s reputation and tenure, brand recognition, performance, and the capabilities and qualifications of each investment firm. We may also consider whether the Fund, its service providers (e.g., the investment adviser or sub-advisers), or its affiliates will make payments to us or our affiliates in connection with certain administrative, marketing, and support services, or whether affiliates of the Fund can provide marketing and distribution support for sales of the Contracts. (For additional information on these arrangements, see the section below entitled “Compensation We Receive from Funds, Advisers and Sub-Advisers.”) We review the Funds periodically and may remove a Fund, or limit its availability to new Purchase Payments and/or transfers of Contract Value if we determine that a Fund no longer satisfies one or more of the selection criteria, and/or if the Fund has not attracted significant allocations from Owners.

Compensation We Receive from Funds, Advisers and Sub-Advisers

Compensation We Receive from Advisers and Sub-Advisers

We and certain of our insurance affiliates receive compensation from the advisers and sub-advisers to some of the Funds. We may use this compensation to pay expenses that we incur in promoting, issuing, distributing and administering the Contract, and in providing services on behalf of the Funds in our role as intermediary to the Funds. The amount of this compensation is determined by multiplying a specified annual percentage rate by the average net assets held in that Fund that are attributable to the variable annuity and variable life insurance products issued by us and our affiliates that offer the particular Fund (MassMutual’s variable contracts). These percentage rates differ, but currently do not exceed 0.25%. Some advisers and sub-advisers pay us more than others; some do not pay us any such compensation.

The compensation may not be reflected in a Fund’s expenses because this compensation may not be paid directly out of a Fund’s assets. These payments also may be derived, in whole or in part, from the advisory fee deducted from Fund assets. Owners, through their indirect investment in the Funds, bear the costs of these advisory fees (see the Funds’ prospectuses for more information).

In addition, we may receive fixed dollar payments from the advisers and sub-advisers to certain funds so that the adviser and sub-adviser can participate in sales meetings conducted by MassMutual. Attending such meetings provides advisers and sub-advisers with opportunities to discuss and promote their funds. For a list of the Funds whose advisers and sub-advisers currently pay such compensation, visit www.MassMutual.com/legal/compensation-arrangements or call our Service Center at the number shown on the cover page of this prospectus.

Compensation We Receive from Funds

We and certain of our affiliates also receive compensation from certain Funds pursuant to Rule 12b-1 under the 1940 Act. This compensation is paid out of the Fund’s assets and may be as much as 0.25% of the average net assets of an underlying Fund which are attributable to MassMutual’s variable contracts. An investment in a Fund with a 12b-1 fee will increase the cost of your investment in the Contract.

Compensation and Fund Selection

The compensation that we receive may be significant and we may profit from this compensation. Additionally, when selecting the Funds that will be available with MassMutual’s variable contracts, we consider the amount of compensation that we receive from the Funds, their advisers, sub-advisers, or their distributors along with the Funds’ name recognition, asset class, the managers’ reputation, and fund performance. We offer certain Funds through the Contract at least in part because they are managed by us or an affiliate.

Voting Rights

We are the legal owner of the Fund shares. When a Fund solicits proxies in conjunction with a vote of shareholders, we are required to obtain, from you and other Contract Owners, instructions as to how to vote those shares.

When we receive those instructions, we will vote all the shares for which we do not receive voting instructions, in proportion to those instructions. This will also include any shares that we own on our own behalf. This may result in a small number of Owners controlling the outcome of a vote. If we determine that we are no longer required to vote shares in accordance with Contract owner instructions, we will vote the shares in our own right.

During the Accumulation Phase, we determine the number of shares you may vote by dividing your Contract Value in each Fund by $100, including fractional shares. You do not have any voting rights during the Annuity Phase.

We may, when required by state insurance regulatory authorities, disregard voting instructions, if such instructions would require shares to be voted so as to cause a change in the sub-classification or investment objective of a fund or to approve or disapprove an investment advisory contract for the fund. In addition, we may disregard voting instructions that would require a change in the investment policy or investment adviser of one or more of the available funds. Our disapproval of such change must be reasonable and based on a good faith determination that the change would be contrary to state law or otherwise inappropriate, considering the fund’s objectives and purpose. If we disregard Owner voting instructions, we will advise Owners of our action and the reasons for such action.

Fixed Account For Dollar Cost Averaging (DCA Fixed Account)

We offer a fixed account for dollar cost averaging (the DCA Fixed Account) as an investment choice under the Contract. Purchase Payments allocated to the DCA Fixed Account become part of our General Account which supports insurance and annuity obligations.

If you are participating in the DCA Fixed Account, the following other features are not available to you: the Automatic Rebalancing Program and Separate Account Dollar Cost Averaging Program.

You may not participate in the DCA Fixed Account if RetirePay is in effect.

Description

The DCA Fixed Account is a fixed account from which assets are systematically transferred to any Sub-Account(s) you select. No transfers may be made to the DCA Fixed Account from any other Fixed Account(s) or Sub-Account maintained under the Contract.

How to Participate in the DCA Fixed Account

You can elect the DCA Fixed Account at the time your Contract is issued or at a later date by submitting a Written Request and applying a Purchase Payment of at least $5,000 to a DCA Term. We reserve the right to reject subsequent Purchase Payments into the DCA Fixed Account to establish a DCA Fixed Account Term.

You cannot transfer current Contract Value into the DCA Fixed Account.

You may apply additional Purchase Payments to a current DCA Term. Such additional Purchase Payments will be added to the amount in the current DCA Fixed Account term for the remaining period of the current DCA Fixed Account term. No transfers may be made to the DCA Fixed Account term from any other Fixed Account(s) or Sub-Account maintained under the Contract. We reserve the right to reject subsequent Purchase Payments into a current DCA Term.

DCA Term

You may elect a DCA Term for a period of either six or 12 months, beginning with the receipt of a new Purchase Payment allocated to the DCA Fixed Account and a Written Request to establish a DCA Term. Only one DCA Fixed

Account term may be operative at a time. If you elect to make an allocation to a DCA Fixed Account, but your Annuity Date will occur prior to the end of that DCA term, your DCA Term will expire on your Annuity Date.

DCA Fixed Account Value

Unless specified otherwise, the DCA Fixed Account value at any time is equal to:

(1)

any Purchase Payments allocated to the DCA Fixed Account; plus

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(2)

Any interest credited to that portion of the Contract Value allocated to the DCA Fixed Account; less

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(3)

Any Contract Value transferred from the DCA Fixed Account; less

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(4)

Any prior withdrawals of Contract Value from the DCA Fixed Account and any applicable charges; less

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(5)

Applicable charges, fees, or taxes.

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With regard to credited interest that is part of the DCA Fixed Account value, we periodically determine the interest rate at our sole discretion, but guarantee that the rate will not be less than the applicable state nonforfeiture interest rate. Interest will be credited daily on the remaining DCA Fixed Account value. The interest rate credited to each Purchase Payment applied to the DCA Fixed Account will not change for the duration of the DCA Fixed Account Term, except to account for any applicable increase to the applicable state nonforfeiture interest rate. We may apply different interest rates to different portions of the DCA Fixed Account value, based upon the date on which a Purchase Payment is applied to the DCA Fixed Account.

A DCA Term will terminate:

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at the scheduled end of the DCA Term;

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if you withdraw the total Contract Value;

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upon our receipt of due proof of the Owner’s death and election of the payment method by any Beneficiary;

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if you apply your entire Contract Value to an Annuity Option; or

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if we receive a Written Request from you to terminate the DCA Fixed Account at our Service Center prior to the next transfer date.

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If the DCA Term terminates due to the Owner’s death or upon Written Request, the remaining value in the DCA Fixed Account will be allocated in accordance with your current allocation instructions, unless you indicate otherwise.

DCA Transfers

Except for the scheduled DCA Fixed Account transfers, no transfers may be made from the DCA Fixed Account before the expiration or termination of the DCA Fixed Account term. DCA Fixed Account transfers will be made on the scheduled transfer dates. If a scheduled transfer date is not a Business Day, the transfer will be made on the next Business Day. Transfers from the DCA Fixed Account are calculated on a first-in, first-out basis, which means the oldest Purchase Payments are transferred first. Scheduled transfers will begin five business days after the establishment of the DCA Term and will be made from the DCA Fixed Account monthly. You may elect to have the scheduled transfers made to any available Sub-Accounts, but not to any other fixed accounts.

Withdrawals When Contract Value Allocated To DCA Fixed Account

If you make a partial withdrawal and you have Contract Value allocated to the DCA Fixed Account, such withdrawal will be made from the Sub-Accounts and fixed account(s) in the ratio that your Contract Value in each Sub-Account and fixed account(s) bears to your Contract Value. Partial withdrawals from the DCA Fixed Account are calculated on a first-in, first-out basis, which means the oldest Purchase Payments are withdrawn first.

Suspension or Deferral of Payments

We reserve the right to suspend or postpone payments for a partial or total withdrawal or transfer from the DCA Fixed Account for a period of up to six months, subject to state insurance department approval, if applicable. With regard to transfers, we will disclose to you the specific date on which the transfer will be effective, the reason for the delay, and the value of the transfer as of the date we receive the request.

Charges and Deductions

This section describes the charges and deductions we make under the Contract to compensate us for the services and benefits we provide, costs and expenses we incur and risks we assume. We may profit from the charges deducted and we may use any such profits for any purpose, including payment of marketing and distribution expenses. These charges and deductions reduce the return on your investment in the Contract.

Insurance Charges

Each Business Day we deduct our insurance charges from the assets of the Separate Account. We do this as part of our calculation of the value of the Accumulation Units and the Annuity Units. The insurance charge has two parts: (1) the mortality and expense risk charge and (2) the administrative charge.

Mortality and Expense Risk Charge

The mortality and expense risk charge is for:

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the mortality risk associated with the insurance benefits provided, including our obligation to make Annuity Payments after the Annuity Date regardless of how long all Annuitants live, the death benefits, and the guarantee of rates used to determine your Annuity Payments during the Annuity Phase; and

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the expense risk that the current charges will be insufficient to cover the actual cost of administering the Contract.

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For all Contracts, if the amount of the charge is more than sufficient to cover the mortality and expense risk, we will make a profit on the charge. We may use this profit for any purpose, including the payment of marketing and distribution expenses for the Contract. If the mortality and expense risk charge is not sufficient to cover the mortality and expense risk, we will bear the loss.

Administrative Charge

This charge reimburses us for the expenses associated with the administration of the Contract and the Separate Account. Some of these expenses are: preparation of the Contract, confirmations, annual reports and statements, maintenance of Contract records, personnel costs, legal and accounting fees, filing fees, and computer and systems costs. This charge is calculated based on a percentage of the daily value of the assets invested in each Fund, after Fund expenses are deducted. The table below reflects the current and maximum charge.

Annual Contract Maintenance Charge

This charge reimburses us for the costs of maintaining the Contract. We will deduct the annual contract maintenance charge proportionately from the Sub-Account(s) you have selected.

Contingent Deferred Sales Charge (CDSC)

We do not deduct a sales charge when we receive a Purchase Payment. However, we may assess a CDSC for withdrawals that exceed the Free Withdrawal Amount, but not against earnings that you withdraw. We use this charge to cover certain expenses relating to the sale of the Contract. The charge is a percentage of the Purchase Payments you withdraw that exceed the Free Withdrawal Amount.

If we assess a CDSC, we will deduct it from the amount you withdraw.

Each Purchase Payment has its own CDSC schedule. The amount of the charge depends on the length of time between the date Purchase Payments were applied and the date of withdrawal. To determine if a CDSC applies, we process withdrawals as follows:

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first from earnings (Contract Value less Purchase Payments not previously withdrawn);

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then from Purchase Payments no longer subject to a CDSC according to the CDSC schedule;

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then from the Free Withdrawal Amount or the amounts attributable to any CDSC waivers (taken from Purchase Payments not previously withdrawn in the order they were received with the oldest Purchase Payment first); and

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then from Purchase Payments not previously withdrawn in the order they were received with the oldest Purchase Payment being first.

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*See “Appendix B – Contingent Deferred Sales Charge (CDSC) Example.”

In addition to the free withdrawals described later in this section, we will not impose a CDSC under the following circumstances:

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Upon payment of the death benefit.

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On amounts withdrawn as RMDs to the extent they exceed the Free Withdrawal Amount. In order to qualify for this exception, (a) you must be participating in a Systematic Withdrawal Program established for the payment of RMDs, under which the annual RMD is calculated by us, based solely on the fair market value of the Contract (RMD program) and (b) you must not take any other withdrawals from the Contract in that Contract Year. If you choose to take withdrawals to satisfy your RMD for the Contract outside of our RMD program, or if you choose to take any other withdrawals from the Contract, CDSCs may apply not only to those withdrawals, but also to any subsequent RMD withdrawals taken under the RMD program in the same Contract Year.

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Upon application of the Contract Value to any Annuity Option.

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If you redeem excess contributions from an IRA. We look to the IRC for the definition and description of excess contributions.

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Under a replacement program offered by us, when the Contract is exchanged for another annuity contract issued by us or one of our affiliated insurance companies, of the type and class which we determine is eligible for such an exchange. A contingent deferred sales charge may apply to the Contract received in the exchange. A reduced CDSC schedule may apply under the Contract if another variable annuity contract issued by us or one of our affiliated insurance companies is exchanged for the Contract. Exchange programs may not be available in all states. If you want more information about our current exchange programs, contact your registered representative or us at our Service Center.

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If you are eligible for waiver of the CDSC due to your election of the Nursing Home and Hospital Withdrawal Benefit or the Terminal Illness Withdrawal Benefit described in “Additional Features.”

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On any withdrawals made when you reach the Latest Permitted Annuity Date for your Contract.

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Free Withdrawal Amount

The Free Withdrawal Amount is an amount of your Purchase Payment(s) that you may withdraw that is not subject to the CDSC. During the first Contract Year, your Free Withdrawal Amount is ten percent (10%) of the Initial Purchase Payment applied on the Issue Date, plus ten percent (10%) of any subsequent Purchase Payments received in that Contract Year. Any available Free Withdrawal Amount during the first Contract Year will be reduced by any Free Withdrawal Amount previously taken during that Contract Year.

During each subsequent Contract Year, your Free Withdrawal Amount is ten percent (10%) of your total Purchase Payments still subject to a CDSC as of the last calendar day of the previous Contract Year, plus 10% of any subsequent Purchase Payments received in the current Contract Year. Any available Free Withdrawal Amount during such Contract Year will be reduced by any Free Withdrawal Amount previously taken during that Contract Year.

Any withdrawal taken during a previous Contract Year may impact the available Free Withdrawal Amount if it results in a decrease in the amount of Purchase Payments still subject to a CDSC.

Any unused Free Withdrawal Amount(s) during any particular Contract Year may not be carried over to any succeeding Contract Year.

Premium Taxes

Some states and other governmental entities charge Premium Taxes or similar taxes. We are responsible for the payment of these taxes and may deduct them from the Purchase Payments or Contract Value, or we may adjust the annuity rates for Premium Tax assessed. Some of these taxes are due when your Contract is issued, others are due when Annuity Payments begin. Premium Taxes generally range from 0% to 3.5%, depending on the state.

Income Taxes

We will deduct from the Contract any income taxes which we incur because of the operation of the Separate Account. We will deduct any withholding taxes required by law.

Fund Expenses

The Separate Account purchases shares of the Funds at net asset value. The net asset value of each Fund reflects investment management fees and other expenses already deducted from the assets of the Fund. In addition, one or more of the Funds available as an investment choice may pay a distribution fee out of the Fund’s assets to us, known as a 12b-1 fee. Any investment in one or more of the Funds with a 12b-1 fee will increase the cost of your investment in the Contract. Please refer to the Fund prospectuses for more information regarding these expenses.

RetirePay Charges

We will assess the RetirePay Charge on a quarterly basis in arrears. On the last calendar day of each Contract Quarter, a charge will be assessed against your Contract Value. The amount that is deducted from your Contract Value is equal to the RetirePay Charge multiplied by the Benefit Base on such day (after taking into account any other transactions processed on such day).

If RetirePay terminates, a pro-rata portion of the RetirePay Charge will generally be assessed based on the number of days from the first calendar day of the current Contract quarter to the date of termination. If you reach your Latest Permitted Annuity Date, and your Contract Value is applied to an Annuity Option, the RetirePay Charge is waived. Once RetirePay has terminated, there will be no further RetirePay Charges assessed. See “Additional Benefits – MassMutual RetirePaySM.”

We deduct the RetirePay Charge pro-rata from each Sub-Account in which you are invested.

The maximum annualized RetirePay Charge is 2.50%. For current RetirePay Charges, see the applicable Rate Sheet Prospectus Supplement attached to your prospectus.

Ownership

Owner

In this prospectus, “you” and “your” refer to the Owner of the Contract. The Owner is named at the time you apply for a Contract. The Owner can be an individual or a non-natural person (e.g., a corporation, limited liability company partnership or certain other entities). The Owner must be at least the age of majority in the state the Contract is issued, and may not be older than Age 85 on the Issue Date. If you elect RetirePay, the Owner must be at least Age 45 and may not be older than Age 80 when the Contract is issued. The maximum issue age for the Contract and certain additional features may be reduced in connection with the offer of the Contract through certain broker-dealers. You should discuss this with your registered representative.

If your Contract is non-qualified and owned by a non-natural person, the Contract will generally not be treated as an annuity for tax purposes. This means that gain in the Contract will be taxed each year while the Contract is in the Accumulation Phase. This treatment is not generally applied to a Contract held by a trust or other entity as an agent for a natural person. Before purchasing a Contract to be owned by a non-natural person or before changing ownership on an existing Contract that will result in it being owned by a non-natural person, you should consult a tax adviser to determine the tax impact. See “Taxes – Non-Natural Owner.”

As the Owner of the Contract, you exercise all rights under the Contract, unless limited by an assignment or by designation of an irrevocable Beneficiary. On or after the Annuity Date, you continue as the Owner.

You may change the Owner of a Non-Qualified Contract at any time by Written Request, subject to our approval. You may not change the Owner(s) without our approval. We will refuse or accept any requested change on a non-discriminatory basis. You may not change the Owner to an individual who was over the maximum age for purchasing the Contract on the Issue Date of the Contract.

A change of Owner will take effect on the date the Written Request is signed, unless you specify otherwise. We will not be liable for any payment made or action taken prior to our receipt and approval of the Written Request. A change of Owner that we allow will automatically revoke any prior designation of Owner. Changing the Owner may result in tax consequences. See “Taxes – Tax Treatment of Assignments” for more information.

Joint Owner

The Contract can be owned by Joint Owners. However, the Contract cannot be jointly owned if it is a Qualified Contract, if an Owner is a non-natural person, or by more than two individuals. The Joint Owner must be at least the age of majority in the state the Contract is issued, and may not be older than Age 85 on the Issue Date. If you elect RetirePay, the Joint Owner must be at least Age 45 and may not be older than age 80 when the Contract is Issued.

If the Contract is jointly owned, we will use the Age of the oldest Owner to determine certain benefits. If there are Joint Owners, we require authorization from both Owners for all transactions.

Annuitant

The Annuitant is the person(s) on whose life (or lives, in the case of joint Annuitants) we base Annuity Payments, with the exception of the non-lifetime contingent option. You designate the Annuitant(s) at the time of application. A Contract may not have more than two Annuitants. There is no minimum age applicable to the Annuitant or joint Annuitant; however, any Annuitant must be at least 18 on the Annuity Date in order for you to elect a life contingent Annuity Option. Annuitants may not be older than Age 85 on the Issue Date. If you elect RetirePay, Annuitants may not be older than Age 80 on the Issue Date.

You may change the Annuitant(s) before the Annuity Date by Written Request, subject to our approval and restrictions that apply if RetirePay is in effect. However, if the Contract is owned by a non-natural person, the Annuitant may not be changed and we will use the Age of the oldest Annuitant to determine certain benefits. The Annuitant generally cannot be changed if the Contract is an individually owned Qualified Contract. We will use the Age of the oldest Annuitant to determine all applicable benefits under a Contract owned by a non-natural person.

When calculating Annuity Payments, we determine Age based on each Annuitant’s nearest birthday on the Annuity Date. See “The Annuity Phase – Annuity Age.”

Any change of Annuitant must be made by Written Request. An approved change will take effect on the date the Written Request is signed, unless you specify otherwise. We will not be liable for any payment made or action taken prior to our receipt of the Written Request. A change of Annuitant that we allow will automatically revoke any prior designation of Annuitant. The Annuitant may not be changed, nor may an Annuitant be added, after the Annuity Date.

Beneficiary

The Beneficiary is the person(s) or entity(ies) you name to receive any death benefit. You name the Beneficiary at the time of application. If the Owner is a non-natural person, the Owner must be the sole primary Beneficiary unless we allow otherwise.

Unless an irrevocable Beneficiary has been named, you can change the Beneficiary by Written Request at any time before you die subject to the restrictions that apply if RetirePay is in effect. If you name an irrevocable Beneficiary but wish to change the Beneficiary, you must deliver written authorization from the irrevocable Beneficiary to our Service Center on our form in Good Order.

A change of Beneficiary will take effect on the date the Written Request is signed, unless you specify otherwise. We will not be liable for any payment made or action taken prior to our receipt of the Written Request.

If there is a joint Annuitant on an individually owned Qualified Contract, the joint Annuitant must also be the sole primary Beneficiary.

Unless you provide otherwise, the death benefit will be paid as follows:

(1)

In equal shares to the primary Beneficiary(ies) who survives your death and/or any Annuitant’s death, as applicable;

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(2)

If there is no primary Beneficiary who survives your death and/or any Annuitant’s death, as applicable, in equal shares to the contingent Beneficiary(ies) who survives your death and/or any Annuitant’s death, as applicable; or

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(3)

If there is no primary or contingent Beneficiary who survives your death and/or any Annuitant’s death, to you or your estate, as applicable.

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We will treat a surviving Owner as the primary Beneficiary and treat any other Beneficiary designation, on record at the time of death, as a contingent Beneficiary.

If the Owner is a non-natural person, the Owner must be the sole primary Beneficiary unless we allow otherwise.

Purchasing a Contract

To purchase a Contract, you must submit your initial Purchase Payment to your registered representative or to us at our Service Center. Once we receive your initial Purchase Payment and the necessary information at our Service Center, we will credit your initial Purchase Payment to your Contract within two Business Days. If you do not give us all of the information we need, we will notify you. When we receive all of the information we need, we will apply your initial Purchase Payment within two Business Days. If we do not have the necessary information to issue your Contract within five Business Days, then we will either return your Purchase Payment or ask your permission to retain your Purchase Payment until all the necessary information is received.

The date when we credit your initial Purchase Payment to your Contract is the Issue Date. We use the Issue Date to determine Contract Years and Contract Anniversaries.

Contract Delay

Our receipt of your initial Purchase Payment may be delayed because of circumstances outside of our control (for example, delays because of the failure of the selling broker-dealer or your registered representative to forward the Purchase

Payment in Good Order to us promptly or because of delays in determining whether the Contract is suitable for you). Any such delays will affect when we can issue your Contract and when your initial Purchase Payment will be allocated among the investment choices under the Contract.

Purchase Payments

The minimum amount we accept for an initial Purchase Payment is:

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$10,000 if you are buying the Contract as a Non-Qualified Contract; or

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$5,000 if you are buying the Contract as a Qualified Contract.

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You can make additional Purchase Payments to your Contract throughout the Accumulation Phase, subject to the conditions noted below. You can make additional Purchase Payments by sending payments to one of our purchase payment processing service centers:

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by check that clearly indicates your name and Contract number, mailed to:

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by Wire Transfer to:

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JP Morgan Chase Bank
New York, New York
ABA #021000021
Massachusetts Mutual Life Insurance Company
Account #323954820
Reference: Annuity Contract #, Name (Your Name)

Additional Purchase Payments of less than $500 are subject to our approval. The maximum total Purchase Payments we will allow without our approval is $1,500,000. In calculating the maximum, we will take into account the cumulative Purchase Payments on the Contract and multiple purchases of the Contract by the same Owner (whether as the sole Owner or Joint Owner), or with the same Annuitant (whether as the Annuitant or joint Annuitant). If RetirePay is in effect with your Contract, you are subject to the restrictions on additional Purchase Payments under the RetirePay Benefit Base provisions. See “Additional Benefits – MassMutual RetirePaySM – Restrictions on Subsequent Purchase Payments” for more information.

If you make additional Purchase Payments, we will credit these amounts to your Contract on the Business Day we receive them and all necessary information, in Good Order, at one of our purchase payment processing service centers. If we receive your Purchase Payment on a Non-Business Day or after the Close of Business, we will credit the amount to your Contract effective the next Business Day.

We reserve the right to reject any application or Purchase Payment. See “Other Information – Reservation of Rights” for more information. Moreover, if RetirePay is in effect with your Contract, we reserve the right to reject any Purchase Payment not conforming to the terms of RetirePay.

Automatic Investment Plan (AIP)

Under the AIP, you may authorize us to periodically draw funds from an account of your choosing (restrictions may apply) for the purpose of making Purchase Payments to your Contract. Contact our Service Center for information regarding setting up an AIP and any restrictions regarding use of the AIP. If you participate in the AIP, the minimum additional Purchase Payment is $100. Additionally, the AIP may not be available for Contracts held as a SEP IRA or SIMPLE IRA.

Allocation of Purchase Payments

When you purchase your Contract, we allocate your Purchase Payment received in Good Order among the investment choices according to the allocation instructions you provide. If you make additional Purchase Payments, we will allocate

them based on your current allocation instructions, unless you request a different allocation by sending us a Written Request. We reserve the right to allocate initial Purchase Payments to a money market Sub-Account, until the expiration of the Right to Examine Contract time period.

Any allocations to the Sub-Accounts that invest in the Funds that you have selected must be in whole percentages and must total 100%.

You may allocate Purchase Payments to the DCA Fixed Account, subject to conditions we may impose on such allocations. See “Transfers and Transfer Programs” for allocation restrictions applicable to that feature.

If you have elected RetirePay, you are subject to restrictions on the allocation of Purchase Payments while RetirePay is in effect. See “Additional Benefits – MassMutual RetirePaySM.” If RetirePay is in effect, changing your current Purchase Payment allocations will change the allocations for any future Purchase Payments as well as transfer Contact Value from your current allocations to your new allocations.

Contract Value

Your Contract Value is the sum of your values in the Sub-Accounts and the DCA Fixed Account.

The value of your investments in the Separate Account will vary depending on the investment performance of the Funds you choose. In order to keep track of your Contract Value in the Separate Account, we use a unit of measure called an Accumulation Unit.

Any Contract Value allocated to the DCA Fixed Account will be credited with a fixed interest rate.

Accumulation Units

Every Business Day we determine the value of an Accumulation Unit for each of the Sub-Accounts. Changes in the Accumulation Unit value reflect the investment performance of the Fund as well as deductions for insurance and other charges. The value of an Accumulation Unit may go up or down from Business Day to Business Day.

When you make a Purchase Payment, we credit your Contract with Accumulation Units. We determine the number of Accumulation Units to credit by dividing the amount of the Purchase Payment allocated to a Sub-Account by the value of the Accumulation Unit for that Sub-Account. When you make a withdrawal, we deduct from your Contract Accumulation Units representing the withdrawal amount.

We calculate the value of an Accumulation Unit for each Sub-Account after the Close of Business each Business Day. Any change in the Accumulation Unit value will be reflected in your Contract Value.

Calculation of Accumulation Unit Value

The Accumulation Unit Value for each Sub-Account was set initially at $10. Subsequently, the Accumulation Unit Values on any Business Day will be those we calculate after the Close of Business on that day. We calculate the Accumulation Unit Values for each Sub-Account by applying the Change in Net Asset Value (NAV) Formula. That formula derives the daily investment rate of return for each Sub-Account net of all Separate Account charges. The Change in NAV Formula is applied to each Sub-Account as follows:

(1)

The daily change in NAV of the Fund is added to the amount of any Fund distribution (income or capital gain distribution) on that Business Day. This sum is then divided by the previous Business Day NAV of the Fund. This is the daily gross investment rate of return for the Fund.

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(2)

The daily accrual for all the Separate Account charges are then subtracted from the daily gross investment rate of return for the Fund.

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(3)

The result is then multiplied by the previous Business Day Accumulation Unit Value to produce the next Accumulation Unit Value.

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We have the right to split or consolidate the number of Accumulation Units credited to your Contract, with a corresponding increase or decrease in the Accumulation Unit Values.

Right to Cancel Your Contract

You have a right to examine your Contract (sometimes referred to as a free look period). If you change your mind about owning your Contract, you can cancel it within ten calendar days after receiving it. This time period may vary by state, but will never be less than ten calendar days.

When you cancel the Contract within this time period, we will not assess a CDSC. Unless your state has other requirements, you will receive back your Contract Value plus any fees or charges previously deducted from your Purchase Payments as of the Business Day we receive your Written Request in Good Order at our Service Center, and your Contract will be terminated. If state law requires us to return the amount of your Purchase Payments, then we will return the greater of: (i) the full amount of any Purchase Payment(s) less any withdrawals, or (ii) your Contract Value plus any fees or charges previously deducted from your Purchase Payments. If you purchase the Contract as an IRA, we will return the greater of your Purchase Payments less any withdrawals, or the Contract Value plus any fees or charges previously deducted from your Purchase Payments. Please see “Appendix G – State Variations of Certain Contract Features” for more information about state variations.

Sending Requests in Good Order

From time to time you may want to submit a request for transfer among investment choices, a withdrawal, a change of Beneficiary, or some other action. We can only act upon your request if we receive it in “Good Order.” To help protect against unauthorized or fraudulent telephone instructions, we will use reasonable procedures to confirm that telephone instructions given to us are genuine. We may record all telephone instructions.

In addition to Written Requests, we may allow requests to our Service Center:

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by fax at (866) 329-4272,

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by e-mail at ANNfax@MassMutual.com,

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by telephone at (800) 272-2216, or

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by internet at www.MassMutual.com.

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Fax, telephone, e-mail, or internet transactions may not always be available. Fax, telephone, and computer systems can experience outages or slowdowns for a variety of reasons. These outages or slowdowns may prevent or delay our receipt of your request. We may make these additional methods available at our discretion. They may be suspended or discontinued at any time without notice. Not all transaction types can be requested by fax, telephone, or the internet.

Transfers and Transfer Programs

General Overview

Generally, you can transfer all or part of your Contract Value among investment choices. However, there are restrictions that are detailed later in this section. You can make transfers by Written Request, e-mail, telephone, fax, or other authorized means. You must clearly indicate the amount and investment choices from and to which you wish to transfer. We reserve the right, at any time, to terminate, suspend, or modify the transfer provisions of the Contract.

Your transfer is effective at the Close of Business on the Business Day we receive your Written Request, in Good Order, at our Service Center. If we receive your transfer request at our Service Center in Good Order on a Non-Business Day or after Close of Business, your transfer request will be effective on the next Business Day.

Transfers During the Accumulation Phase

You may transfer all or part of your Contract Value allocated to a Sub-Account. You can make a transfer to or from any Sub-Account. If your Contract has RetirePay in effect, there are restrictions on available Sub-Accounts. See “Benefits Available Under The Contract – MassMutual RetirePaySM.”

Currently, we do not limit the number of transfers you may make; however, we reserve the right to limit transfers when the transfer privilege is being exercised to the detriment of other Owners. We further reserve the right, upon 30 calendar days advance notice to you, to limit the number of transfers in the future. We will exercise this right should we see a significant increase in transfer activity by Owners that leads to an increase in cost to administer the Contract. If we exercise this right, we will do so in the same manner for all Owners, and we will provide Owners with prior Written Notice of our decision to limit the number of transfers you may make.

Transfers During the Annuity Phase

We do not allow transfers during the Annuity Phase.

Transfer Programs

For detailed rules and restrictions pertaining to these programs and instructions for electing a program contact our Service Center.

Overview

We currently offer the following transfer programs: Separate Account Dollar Cost Averaging Program and Automatic Rebalancing Program. These programs are available only during the Accumulation Phase. You may participate in only one of these programs at any one time.

You may not participate in the Separate Account Dollar Cost Averaging Program or the Automatic Rebalancing Program if you have a current election in the DCA Fixed Account.

You may not participate in the Separate Account Dollar Cost Averaging Program or Automatic Rebalancing Program if RetirePay is in effect.

Separate Account Dollar Cost Averaging Program

This program allows you to systematically transfer a set amount from a Sub-Account to any of the other Sub-Account(s). By allocating amounts on a regular schedule as opposed to allocating the total amount at one particular time, you may be less susceptible to the impact of market fluctuations. Dollar cost averaging does not assure a profit and does not protect you against loss in declining markets. Since dollar cost averaging involves continuous investment in securities regardless of fluctuating price levels of such securities, you should consider your financial ability to continue the program through periods of fluctuating price levels.

Your Separate Account Dollar Cost Averaging Program will terminate:

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if you withdraw the total Contract Value;

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upon our receipt of due proof of the Owner’s death and election of the payment method by any Beneficiary;

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if the last transfer you selected has been made;

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if there is insufficient Contract Value in the selected Sub-Account to make the transfer; or

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if we receive from you a Written Request or a request over the telephone to terminate the program at our Service Center prior to the next transfer date.

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Automatic Rebalancing Program

Over time, the performance of each Sub-Account may cause your allocation to shift from your original allocation. You can direct us to automatically rebalance your Contract Value allocated to the Sub-Accounts in order to return to your original percentage allocations by selecting our Automatic Rebalancing Program.

This program will terminate:

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if you withdraw the total Contract Value;

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upon our receipt of due proof of the Owner’s death and election of the payment method by any Beneficiary;

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if we receive any unscheduled transfer request; or

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if we receive from you a Written Request or request over the telephone to terminate the program at our Service Center prior to the next transfer date.

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Limits on Frequent Trading and Market Timing Activity

The Contract and its investment choices are not designed to serve as vehicles for what we have determined to be frequent trading or market timing trading activity. We consider these activities to be abusive trading practices that can disrupt the management of a Fund in the following ways:

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by requiring the Fund to keep more of its assets liquid rather than investing them for long-term growth, resulting in lost investment opportunity; and

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by causing unplanned portfolio turnover.

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These disruptions, in turn, can result in increased expenses and can have an adverse effect on Fund performance that could impact all Owners and Beneficiaries under the Contract, including long-term Owners who do not engage in these activities. Therefore, we discourage frequent trading and market timing trading activity and will not accommodate frequent transfers of Contract Value among the Funds. Organizations and individuals that intend to trade frequently and/or use market timing investment strategies should not purchase the Contract.

We have adopted policies and procedures to help us identify those individuals or entities that we determine may be engaging in frequent trading and/or market timing trading activities. We monitor trading activity to uniformly enforce those procedures. However, those who engage in such activities may employ a variety of techniques to avoid detection. Our ability to detect frequent trading or market timing may be limited by operational or technological systems, as well as by our ability to predict strategies employed by Owners (or those acting on their behalf) to avoid detection. Therefore, despite our efforts to prevent frequent trading and the market timing of Funds among the Sub-Accounts, there can be no assurance that we will be able to identify and curtail every instance of trading of those who trade frequently or those who employ a market timing strategy or those who act as intermediaries on behalf of such persons. Moreover, our ability to discourage and restrict frequent trading or market timing may be limited by decisions of state regulatory bodies and court orders that we cannot predict.

In addition, some of the Funds are available with variable products issued by other insurance companies. We do not know the effectiveness of the policies and procedures used by these other insurance companies to detect frequent trading and/or market timing. As a result of these factors, the Funds may reflect lower performance and higher expenses across all Contracts as a result of undetected abusive trading practices.

If we, or any investment adviser to any of the Funds available with the Contract, determine that an Owner’s transfer patterns reflect frequent trading or employment of a market timing strategy, we will allow the Owner to submit transfer requests by regular mail only. We will not accept other Owner transfer requests if submitted by overnight mail, fax, the telephone, our website, or any other type of electronic medium. Additionally, we may reject any single trade that we determine to be abusive or harmful to the Fund. Orders for the purchase of Fund shares may be subject to acceptance by the Fund. Therefore, we reserve the right to reject, without prior notice, any Fund transfer request if the investment in the Fund is not accepted for any reason.

The Funds may assess a redemption fee (which we reserve the right to collect) on shares held for a relatively short period. The prospectuses for the Funds describe the Funds’ frequent trading and market timing policies and procedures, which may be more or less restrictive than the policies and procedures we have adopted. We have entered into a written agreement, as required by SEC regulation, with each Fund or its principal underwriter that obligates us to provide to the Fund promptly upon request certain information about the trading activity of individual Owners, and to execute instructions from the Fund to restrict or prohibit further purchases or transfers by specific Owners who violate the frequent trading or market timing policies established by the Fund.

Owners and other persons with interests in the Contracts should be aware that the purchase and redemption orders received by the Funds generally are “omnibus” orders from intermediaries, such as retirement plans or separate accounts funding variable insurance contracts. The omnibus orders reflect the aggregation and netting of multiple orders from individual owners of variable contracts and/or individual retirement plan participants. The omnibus nature of these orders

may limit the Funds in their ability to apply their frequent trading or market timing policies and procedures. It may also require that we restrict or prohibit further purchases or transfers as requested by a Fund on all contracts owned by an Owner whose trading activity under one variable contract has violated a Fund’s frequent trading or market timing policy. If a Fund believes that an omnibus order reflects one or more transfer requests from Owners engaged in frequent trading or market timing activity, the Fund may reject the entire omnibus order.

We will notify you in writing if we reject a transfer or if we implement a restriction due to frequent trading or the use of market timing investment strategies. If we do not accept a transfer request, no change will be made to your allocations per that request. We will then allow you to resubmit the rejected transfer by regular mail only.

Additionally, we may in the future take any of the following restrictive actions that are designed to prevent the employment of a frequent trading or market timing strategy:

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not accept transfer instructions from an Owner or other person authorized to conduct a transfer;

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limit the number of transfer requests that can be made during a Contract Year; and

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require the value transferred into a Fund to remain in that Fund for a particular period of time before it can be transferred out of the Fund.

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We will apply any restrictive action we take uniformly to all Owners we believe are employing a frequent trading or market timing strategy. These restrictive actions may not work to deter frequent trading or market timing activity.

We reserve the right to revise our procedures for detecting frequent trading and/or market timing at any time without prior notice if we determine it is necessary to do so in order to better detect frequent trading and/or market timing, to comply with state or federal regulatory requirements, or to impose different restrictions on frequent traders and/or market timers. If we modify our procedures, we will apply the new procedure uniformly to all Owners.

The Annuity Phase

Overview

If you want to receive regular income from your Annuity, you can elect to apply your Contract Value so that you can receive Fixed Annuity Payments under one of the Annuity Options described in this section. If you have reached your Annuity Date and you have not chosen an Annuity Option, we will assume you elected a Single Life Annuity with Period Certain Annuity Option with fixed payments and ten years of payments guaranteed. If the Contract has joint Annuitants, we will assume you elected the Joint and Survivor Life Annuity Option with fixed payments and ten years of payments guaranteed. If your Contract is a Qualified Contract, additional requirements may apply. We may base Annuity Payments on the Age and sex of the Annuitant under all options except the Non-Lifetime Contingent Annuity Option. We consider a Non-Lifetime Contingent Annuity Option to be an Annuity Option which provides an Annuity Payment for a fixed period of time only. See “The Annuity Phase – Non-Lifetime Contingent Option – Period Certain Annuity Option.” We may require proof of Age and sex before Annuity Payments begin.

You may only apply your full Contract Value to an Annuity Option. If the amount to be applied under an Annuity Option results in an Annuity Payment of less than $20 monthly (or the equivalent amount based on the selected frequency), we will pay the amount in a lump sum. If any Annuity Payment is less than $100, we will change the payment basis to equivalent quarterly, semi-annual or annual payments.

Annuity Payment Start Date

You can choose the day, month and year in which Annuity Payments begin; however, the day must be between the 1st and 28th day of the month. We call that date the Annuity Date. According to your Contract, your Annuity Date cannot be earlier than five years after you buy the Contract (unless state law requires a shorter waiting period).

When you purchase the Contract, your Annuity Date is the Latest Permitted Annuity Date. After you purchase your Contract you can request an earlier Annuity Date by Written Request. If you have elected an Annuity Date earlier than your Latest Permitted Annuity Date, you can request that we delay your Annuity Date by Written Request or by telephone any time before the Annuity Date.

Latest Permitted Annuity Date

Unless the laws or regulations of the state in which your Contract was issued requires an earlier date, Annuity Payments must begin by the Contract Anniversary after the 95th birthday of the oldest Annuitant or the oldest Owner (whichever is sooner).

Annuity Payments

On the Annuity Date, you will begin receiving Annuity Payments under the Annuity Option that you elected. Your Annuity Payments will be fixed, meaning that the payments will not vary unless you elect either of the Joint and 2/3 Survivor Annuity Options that reduce payments upon the death of the first Annuitant. The amount of your Annuity Payments will depend upon the following:

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the value of your Contract on the Annuity Date;

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the Annuity Option you elect;

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the Age and sex of the Annuitant or joint Annuitants, if applicable;

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the minimum guaranteed payout rates associated with your Contract; and

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the deduction of Premium Taxes, if applicable.

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Generally, the more frequently the Annuity Payments will be made or the longer the Annuity Period will last, the lower the amount of your Annuity Payments will be.

See “Fixed Annuity Payout Rates” section in the SAI for more information.

Annuity Age

When calculating Annuity Payments, we determine Age based on each Annuitant’s nearest birthday on the Annuity Date. For example, we consider age 80 to be the period of time between age 79 years, 6 months, and 1 day and age 80 years and 6 months.

Annuity Options

The available fixed Annuity Options are listed in this section in the Annuity Options table. We may consent to other plans of payment in addition to those listed. After Annuity Payments begin, you cannot change the Annuity Option or the frequency of Annuity Payments. Generally, you cannot make withdrawals during the Annuity Phase; however, certain Annuity Options may allow for commuted value withdrawals. See “The Annuity Phase – Annuity Payment Commutation.” For all lifetime contingent Annuity Options, the Annuitant(s) must be at least age 18 as of the Annuity Date.

RMDs for Qualified Contracts

In order to avoid adverse tax consequences, you should begin to take distributions from your Contract no later than the beginning date required by the IRC. These distributions can be withdrawals or Annuity Payments. The distributions should be at least equal to the minimum amount required by the IRC or paid through an Annuity Option that complies with the RMD rules of IRC Section 401(a)(9). If your Contract is an individual retirement annuity, the required beginning date is no later than April 1 of the calendar year: (1) after you reach age 72, if you were born after June 30, 1949 or (2) after you reach age 701∕2, if you were born before July 1, 1949.

Contingent Deferred Sales Charge (CDSC)

We will not deduct a CDSC if you apply your Contract Value to any Annuity Option.

Limitations on Payment Options

If you purchased the Contract as a Qualified Contract, the RMD rules that apply to annuitized Contracts during your lifetime may impose restrictions on the types of payment options that you may elect. In addition, in order to ensure that the Contract will comply with the RMD requirements that apply upon your death, you may not elect a joint and survivor annuity option with a non-spouse Joint Annuitant who is more than 10 years younger than you.

For Qualified Contracts, if, upon the death of the owner (annuitant if the contract is held as a Custodial IRA), there are annuity payments remaining, we may shorten the remaining payment period in order to ensure that payments do not continue beyond the 10 year post-death distribution period provided under IRC section 401(a)(9), or beyond the beneficiary’s life or life expectancy for certain classes of beneficiaries, such as a spouse or an individual who is not more than 10 years younger than the decedent. In such a case, the adjusted payment stream will be calculated by first calculating the commuted value of the remaining payments, and then calculating an actuarially equivalent payment stream over the revised period, using the same rate used in the commutation calculation.

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(1)

We consider this Annuity Option to be a non-lifetime contingent Annuity Option.

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Annuity Payment Commutation

Once during lifetime of the Contract, you may, upon Written Request, withdraw all or a portion of the Commuted Value of any remaining Period Certain Annuity Payments, subject to the following conditions:

This commutation right is only available for use with the following Annuity Options:

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Single Life Annuity – Period Certain for 10 or 20 years; or

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Joint and Survivor Life Annuity – Period Certain for 10 or 20 years, with or without a reduction; or

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Period Certain Annuity Only – 10 years or greater.

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A commuted value withdrawal:

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may not be taken any earlier than one year following the date you apply your Contract Value to an Annuity Option;

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may not be taken after the end of the Period Certain portion of the Annuity Phase;

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may not be taken if the requested withdrawal would cause the remaining Annuity Payment to be less than the Minimum Annuity Payment payable under the Contract at the existing Annuity Payment frequency; and

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must be at least $10,000.

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The Commuted Value of the remaining Period Certain Annuity Payments is calculated using the Commuted Value Formula specified on the Contract Schedule. All Commuted Values will be determined upon our receipt of a Written Request at our Service Center. Upon receipt of such Written Request, we will provide you with a notice of the amount payable, how the amount was determined and the impact on remaining Annuity Payments, if applicable.

For Period Certain Only Annuity Options, future Annuity Payments will be proportionally reduced by the ratio of the amount of the withdrawal to the Commuted Value. If the full Commuted Value is withdrawn, no future Annuity Payments will be made, and the Contract will terminate.

For Life Contingent Period Certain Annuity Options, future Annuity Payments during the remaining Period Certain will be proportionally reduced by the ratio of the amount of the withdrawal to the Commuted Value. Any future life contingent Annuity Payments will revert to the scheduled payment amount at the end of the Period Certain as long as an Annuitant is alive.

Benefits Available Under the Contract

The following table summarizes information about the benefits available under the Contract. 

Some of the benefits identified in the Table of Benefits Available Under the Contract are described in more detail following the table and other benefits are disclosed in more detail in other sections of the prospectus.

Death Benefit

Death of Owner During the Accumulation Phase

If you, or any Joint Owner, die during the Accumulation Phase, we will pay a death benefit to the primary Beneficiary. If any Owner dies, we will treat the surviving Owner as the primary Beneficiary and treat any other Beneficiary designation, on record at the time of death, as a contingent Beneficiary.

The Beneficiary may request that the death benefit be paid under one of the death benefit options. If the sole primary Beneficiary is your spouse and your Contract is a Non-Qualified Contract or is held as a traditional IRA (including SEP and SIMPLE IRAs) or Roth IRA, he or she may elect to become the Owner of the Contract by continuing the Contract at the death benefit amount payable. Generally, if the Contract is continued then:

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the initial Contract Value will equal the death benefit amount;

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all applicable Contract features and benefits will be in the surviving spouse’s name; and

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the surviving spouse will exercise all of the Owner’s rights under the Contract.

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Restrictions are as follows:

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if, at the time the Owner purchased the Contract, the surviving spouse was over the maximum contract issue age, then the Contract cannot be continued;

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if the surviving spouse is not a Covered Person, RetirePay will be terminated.

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If the sole primary Beneficiary is a domestic partner or civil union partner, as defined under applicable state laws, we will treat him or her as a spouse for this provision, and he or she may elect to continue the Contract as described herein. However, a domestic partner or civil union partner cannot elect to continue the Contract if it is a traditional IRA or Roth IRA. Since current federal tax law does not define a spouse to include a domestic partner or civil union partner, such domestic partner or civil union partner who elects to continue the Contract must still meet the distribution requirements of IRC Section 72(s). In order to meet these requirements, the amount of any gain in the Contract will become subject to income tax at the time the election to continue the Contract is made.

The right to continue the Contract by a surviving spouse, a domestic partner, or a civil union partner can only be exercised once while the Contract is in effect.

See “Taxes – Civil Unions and Domestic Partnerships” if you are in a domestic partnership or civil union.

Death Benefit Amount During the Accumulation Phase

Return of Purchase Payment Death Benefit

The death benefit during the Accumulation Phase will be the greater of 1 and 2 below.

(1)

The total Purchase Payments, reduced by an adjustment for each withdrawal. The adjustment is equal to A divided by B, with the result multiplied by C, where:

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A = the Contract Value withdrawn, including any applicable CDSC;

B = the Contract Value immediately prior to the withdrawal; and

C = the total Purchase Payments adjusted for any prior withdrawals.

(2)

The Contract Value.

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A withdrawal will reduce the death benefit amount in direct proportion to the Contract Value reduction, including withdrawals of the Annual Lifetime Benefit Amount if RetirePay is in effect. For example, if you take a 20% withdrawal from your Contract Value, the death benefit will be reduced by 20%. Since withdrawals result in a pro rata adjustment to the death benefit amount, the death benefit amount will be reduced by more than the actual dollar amount of the withdrawals when the death benefit is greater than the Contract Value. See “Appendix D – Return of Purchase Payment Death Benefit Examples.”

The death benefit that is payable during the Accumulation Phase is determined as of the Close of Business on the Business Day on which we receive both due proof of death and an election of a payment method at our Service Center in Good Order. Where there is more than one Beneficiary, we will determine the death benefit as of the Close of Business on the first Business Day that any Beneficiary submits due proof of death and election of a payment method in Good Order. If the death benefit payable is greater than the Contract Value, we will apply an amount equal to the difference between the death benefit and Contract Value to each Sub-Account and/or the DCA Fixed Account, if applicable, in the ratio that your value bears to your Contract Value. Any current DCA Term will then terminate. Each Beneficiary’s portion of the death benefit will be applied to their chosen death benefit payout option on the Business Day we receive their election of a payment method at our Service Center in Good Order, and will be paid from the Sub-Accounts on a pro rata basis. The balance of the death benefit will remain in the Sub-Accounts based on the current allocation until each of the other Beneficiaries submits their election of a payment method to our Service Center in Good Order. From the time the death benefit is determined until complete distribution is made, any amount in a Sub-Account will be subject to investment risk. This risk is borne by the Beneficiary(ies).

The Return of Purchase Payment Death Benefit will terminate if the Contract terminates, once the Contract enters the Annuity Phase, or upon our receipt of due proof of the Owner’s death and election of the payment method unless the Contract is continued by the surviving spouse.

Death Benefit Payment Options During the Accumulation Phase

The availability of certain death benefit options may be limited for tax-qualified contracts in order to comply with RMD rules.

For Non-Qualified Contracts, each Beneficiary must elect the death benefit to be paid under one of the following options in the event that a death benefit becomes payable during the Accumulation Phase:

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Option 1 – Lump sum payment of the death benefit.

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Option 2 – Payment of the entire death benefit within five years of the date of any Owner’s death. This option may not be available if there are multiple Beneficiaries.

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Option 3 – Payment of the death benefit under an Annuity Option over the lifetime of the Beneficiary or over a period not extending beyond the life expectancy of the Beneficiary. Distribution must begin within one year of the date of any Owner’s death. This option is not available for a Beneficiary that is a non-natural person.

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For Qualified Contracts, each Beneficiary must elect the death benefit to be paid under one of the following options in the event that a death benefit becomes payable during the Accumulation Phase:

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Option 1 – Lump sum payment of the death benefit.

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Option 2 – Payment of the entire death benefit by the end of the calendar year that contains the tenth anniversary of your death. This option may not be available if there are multiple Beneficiaries.

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Option 3 – If the Beneficiary is your surviving spouse, or is not more than ten years younger than you, payment of the death benefit under an Annuity Option over the lifetime of the Beneficiary or over a period not extending beyond the life expectancy of the Beneficiary. Distribution must generally begin by the end of the calendar year following the year of your death. Additional deferral may be available for a spouse Beneficiary.

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Option 4 – If the Beneficiary is your surviving spouse, or is not more than ten years younger than you, payment of the death benefit from a deferred annuity Contract over the life expectancy of the Beneficiary through a series of non-annuitized withdrawals made at least annually. Distribution must generally begin by the end of the calendar year following the year of your death. Additional deferral may be available for a spouse Beneficiary. Additional withdrawals, including full withdrawals, are available. This option may not be available if there are multiple Beneficiaries. See “Death Benefit – Death Benefit Payment Options During the Accumulation Phase – Beneficiary IRA” for rules and restrictions.

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If the sole primary Beneficiary is a spouse, continuation of the Contract in his or her own name is described previously in this section under “Death Benefit – Death of Owner During the Accumulation Phase.”

For Non-Qualified Contracts, any portion of the death benefit not applied to Option 3 within the time period specified must be distributed within five years of the date of the Owner’s death under Option 1 or Option 2. For Qualified Contracts, any portion of the death benefit not applied to Option 3 or Option 4 within the time period specified must be distributed by the end of the calendar year that contains the tenth anniversary of your death under Option 1 or Option 2. This is true even if you have restricted the Beneficiary’s payout option. You may restrict a Beneficiary’s right to elect a death benefit payout option. If you do so, such rights or options will not be available to the Beneficiary.

We may also consent to other death benefit payout options in addition to those described in this section as long as they comply with IRC Section 72(s) or Section 401(a)(9), as applicable.

If a Beneficiary chooses to receive payment of the Death Benefit other than as a lump sum, their successor beneficiary will only receive any remaining Contract Value in the event of death before full distribution has been made. The ROP Death Benefit will not apply upon the death of the Beneficiary.

Lump Sum Payments

If a lump sum payment is requested, we will pay the amount within seven calendar days after we receive proof of death and election of the payment method in Good Order at our Service Center, unless we are required to suspend or delay payment.

Beneficiary IRA

Beneficiary, Inherited, Legacy or “Stretch” IRAs are all terms used to describe an IRA that is used exclusively to distribute death proceeds of an IRA or other qualified investment to the Beneficiary over that Beneficiary’s life expectancy in order to meet the required minimum distribution (RMD) rules. Upon the Contract Owner’s death under an IRA or other qualified Contract, an “eligible designated beneficiary(ies)” may generally establish a Beneficiary IRA by either purchasing a new annuity Contract or, in some circumstances, by electing the Beneficiary IRA payout option under the current Contract. Until withdrawn, amounts in a Beneficiary IRA continue to be tax-deferred. Amounts withdrawn each year, including amounts that are required to be withdrawn under the RMD rules, are subject to tax.

If the Contract Owner died on or before December 31, 2019 (on or before December 31, 2021 for participants of a governmental plan or a plan maintained pursuant to a collective bargaining agreement), an individual designated Beneficiary, and certain trusts as Beneficiary, are treated as eligible designated Beneficiaries, and can elect to take distributions over their life expectancy (life expectancy of the oldest trust Beneficiary).

However, if the Contract Owner dies on or after January 1, 2020 (on or after January 1, 2022 for participants of a governmental plan or a plan maintained pursuant to a collective bargaining agreement), only certain designated Beneficiaries are treated as eligible designated Beneficiaries, and we will only offer the Beneficiary IRA payout option to a designated Beneficiary who either (1) is the surviving spouse of the deceased qualified plan participant or IRA owner or, (2) is not more than 10 years younger than the deceased qualified plan participant or IRA owner. In the future, we may allow additional classes of eligible designated Beneficiaries to elect the Beneficiary IRA payout option. See “Death Benefit – Death Benefit Payment Options During the Accumulation Phase” for more information.

See “Taxes – Required Minimum Distributions for Qualified Contracts” for more information.

Eligibility Requirements/Restrictions:

If a Beneficiary(ies) elects payment under Option 4 as a Beneficiary IRA after the death of the Owner, the following rules apply:

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The annuity Contract will be titled in the Beneficiary’s name as Beneficiary for the deceased Owner. The Beneficiary must be the Annuitant, and the Annuitant cannot be changed.

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For non-spousal Beneficiary IRAs, RMDs must begin by December 31st of the year following the year of the date of the Owner’s death. For spousal Beneficiary IRAs, RMDs may be deferred until the year for which the original Owner would have been required to begin RMDs. The RMD amount will generally be calculated based on the Beneficiary’s life expectancy and will be withdrawn from each Sub-Account and/or the DCA Fixed Account, if applicable, in the ratio that your value in each bears to your Contract Value.

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We will not offer a Beneficiary IRA to a trust.

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RMDs must be made at least annually through a SWP that we administer. The SWP cannot be terminated.

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Withdrawals will not be subject to a CDSC.

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The Beneficiary’s initial Contract Value will be equal to the death benefit that would have been payable to the Beneficiary if a lump sum distribution had been elected.

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Additional contributions cannot be applied to the Contract.

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Upon the death of the Annuitant, any remaining Contract Value will be paid to the succeeding Beneficiary in a lump sum or over the Annuitant’s remaining life expectancy as determined by the applicable IRS table, but in no case may payments extend beyond the end of the calendar year that contains the tenth anniversary of the Annuitant’s death.

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A Beneficiary IRA may only be established by the Beneficiary of the IRA owner/qualified plan participant whose death triggered the RMD requirements of IRC Section 401(a)(9). A Beneficiary IRA may not be established as a “second generation” Beneficiary IRA by a successor Beneficiary.

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Joint ownership of a Beneficiary IRA is not allowed.

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If RetirePay is in effect, it will be terminated.

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Beneficiaries should consult a qualified tax adviser for advice prior to establishing a Beneficiary IRA.

Death of Owner During the Annuity Phase

Upon any Owner’s death during the Annuity Phase, if the Annuitant is still alive, the surviving Owner will retain the ownership of the Contract. If there is no surviving Owner, the Beneficiary will become the Owner. Any remaining Annuity Payments under the Annuity Option elected will continue to be paid at least as rapidly as under the method of distribution in effect at such Owner’s death. For Qualified Contracts, the Beneficiary(ies) may be required to receive an adjusted payment stream in order to comply with RMD rules that apply upon the Owner/Annuitant’s death. If the Beneficiary is not an “Eligible Designated Beneficiary” as defined by IRC Section 401(a)(9), Annuity Payments may only continue through the end of the calendar year that contains the tenth anniversary of the Owner/Annuitant’s death, even if a longer Annuity Payment option was elected, including a Joint and Last Survivor Annuity Option where the Joint Annuitant is still living.

Death of Annuitant

If an Annuitant, who is not the Owner or Joint Owner, dies during the Accumulation Phase, you can name a new Annuitant subject to our approval. If there is no surviving Annuitant, the oldest Owner will become the Annuitant. If the Owner is a non-natural person and an Annuitant dies, you may not name a new Annuitant. In this case we will treat the death of the Annuitant as the death of the Owner and pay the death benefit as described in “Death Benefit – Death of Owner During the Accumulation Phase.”

Upon the death of the last surviving Annuitant on or after the Annuity Date, the death benefit, if any, is as specified in the Annuity Option elected. Upon the death of the last surviving Annuitant during the Annuity Phase, any remaining payment under the elected Annuity Option will be paid to the Beneficiary. For Qualified Contracts, the Beneficiary(ies) may be required to receive an adjusted payment stream in order to comply with RMD rules that apply upon the Owner/​Annuitant’s death. If the Beneficiary is not an “Eligible Designated Beneficiary” as defined by IRC Section 401(a)(9), Annuity Payments may only continue through the end of the calendar year that contains the tenth anniversary of the Owner/ Annuitant’s death, even if a longer Annuity Payment option was elected, including a Joint and Last Survivor Annuity Option where the Joint Annuitant is still living. We will treat a surviving Owner as the primary Beneficiary and treat any other Beneficiary designation on record at the time of death as a contingent Beneficiary.

Due Proof of Death

For purposes of determining due proof of death, we require:

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a certified death certificate; or

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a certified decree of a court of competent jurisdiction as to the finding of death; or

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any other proof satisfactory to us.

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Additional Benefits

Terminal Illness Withdrawal Benefit

With this benefit, you may withdraw all or a portion of your Contract Value without incurring a CDSC if we receive a Written Request in Good Order at our Service Center that you (or an Annuitant, if the Owner is a non-natural person) have met the following conditions:

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For purposes of this benefit, you (or an Annuitant, if the Owner is a non-natural person) were not diagnosed with a terminal illness or a terminal condition resulting from bodily injury or disease or both as of the Issue Date.

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Each withdrawal request is made on or after the “Eligibility Date for Waiver of Contingent Deferred Sales Charge,” which is one year after the Issue Date.

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We will require proof that you (or an Annuitant, if the Owner is a non-natural person) are terminally ill, as described above, and not expected to live more than 12 months. This proof will include, but is not limited to, certification by a state licensed medical practitioner performing within the scope of his/her license. The state licensed medical practitioner must not be you or your parent, sibling, spouse or child (or an Annuitant or an Annuitant’s parent, sibling, spouse or child if the Owner is a non-natural person).

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If we determine that your Written Request for a withdrawal free of CDSC does not meet the qualifying conditions, we will provide a Written Notice of such determination. We will not proceed with your Written Request for a withdrawal until

we receive notification from you that you accept or reject the withdrawal including the CDSC assessed. If you do not accept the withdrawal including the CDSC, the withdrawal request will not be processed. If you do accept the withdrawal including the CDSC, we will process it on the Business Day you notify us of your acceptance.

There is no charge for the Terminal Illness Withdrawal Benefit. The Terminal Illness Withdrawal Benefit may not be available in all states. See “Appendix G – State Variations of Certain Contract Features.” Please contact your registered representative or call the Service Center for more information.

Nursing Home and Hospital Withdrawal Benefit

With this benefit, you may withdraw all or a portion of your Contract Value without incurring a CDSC if we receive a Written Request in Good Order at our Service Center that you (or an Annuitant, if the Owner is a non-natural person) have been admitted to a licensed nursing care facility or accredited hospital or its successor, subject to the following requirements:

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For purposes of this benefit, you (or the Annuitant, if the Owner is a non-natural person) are not confined in a licensed nursing care facility or accredited hospital or its successor on the Issue Date.

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Each withdrawal request is made on or after the “Eligibility Date for Waiver of Contingent Deferred Sales Charge,” which is one year after the Issue Date.

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Each withdrawal request is made within 120 calendar days after services were provided to you (or the Annuitant, if the Owner is a non-natural person). You must have been confined at a licensed nursing care facility and/or accredited hospital or its successor for a consecutive period of at least 90 consecutive calendar days.

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The confinement must be prescribed by a state licensed medical practitioner performing within the scope of his/her license.

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Each withdrawal is accompanied by proof satisfactory to us that you (or the Annuitant, if the Owner is a non-natural person) meet the qualifying conditions above.

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You may not participate in the Systematic Withdrawal Program if we are currently waiving the CDSC in accordance with this benefit.

A licensed nursing care facility is an institution licensed by the state in which it is located to provide skilled nursing care, intermediate nursing care, or custodial nursing care. An accredited hospital is a hospital licensed, or recognized as a general hospital, by the state in which it is located or by the Joint Commission on the Accreditation of Hospitals, or its successors.

If we determine that your Written Request for a withdrawal free of CDSC does not meet the qualifying conditions, we will provide a Written Notice of such determination. We will not proceed with your Written Request for a withdrawal until we receive notification from you that you accept or reject the withdrawal including the CDSC assessed. If you do not accept the withdrawal including the CDSC, the withdrawal request will not be processed. If you do accept the withdrawal including the CDSC, we will process it on the Business Day you notify us of your acceptance.

There is no charge for the Nursing Home and Hospital Withdrawal Benefit. The Nursing Home and Hospital Withdrawal Benefit may not be available in all states. See “Appendix G – State Variations of Certain Contract Features.” Please contact your registered representative or call the Service Center for more information.

MassMutual RetirePaySM

We offer an optional guaranteed lifetime withdrawal benefit (“RetirePay”) under the Contract. RetirePay guarantees that each Contract Year beginning with the Guaranteed Lifetime Withdrawal Date, you can receive guaranteed lifetime income equal to the Annual Lifetime Benefit Amount even if your Contract Value is reduced to zero as long as there is a positive Benefit Base. However, you will not receive that guaranteed lifetime income if your Contract Value is reduced to zero due to a withdrawal prior to the Guaranteed Lifetime Withdrawal Date or due to an Excess Withdrawal.

There are two versions of RetirePay: a single life version and a joint life version. For each version, there are two Automatic Step-Up options.

Rate Sheet Prospectus Supplement Information

We use the Rate Sheet Prospectus Supplement (“Rate Sheet”) to provide current information about the RetirePay Guaranteed Lifetime Withdrawal Benefit as of a certain effective date. The Rate Sheet updates the following information regarding RetirePay:

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Withdrawal Rates,

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Lifetime Guarantee Rates,

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RetirePay Charges, and

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Investment Allocation Restrictions

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(collectively, referred to as the “RetirePay Terms”).

A Rate Sheet that supersedes a prior Rate Sheet will not become effective unless Written Notice of the effective date of the new Rate Sheet is given at least 10 Business Days in advance. The relevant information from all superseded Rate Sheets can be found in Appendix H to this prospectus.

Rate Sheet Eligibility Conditions

Certain Rate Sheet eligibility conditions apply when we have issued a subsequent Rate Sheet after you apply for your contract and prior to your issue date.

In order for the RetirePay Terms in any particular Rate Sheet to apply to your Contract, your necessary application information, including any applicable transfer form(s), must be submitted to an order entry system utilized to issue the Contract (“application submit date”) on or after the effective date of that Rate Sheet and prior to the effective date of the subsequent Rate Sheet. For purposes of this process, the application submit date is also defined to include the date the application is signed if a paper application is necessary.

Application Information Submitted with a Purchase Payment

In addition to the submission of your necessary application information, we also require payment of at least the minimum initial Purchase Payment and the application information to be in Good Order within 10 Business Days after the application submit date.

If these Rate Sheet Eligibility Conditions are met, and the Contract is issued, the RetirePay Terms in the Rate Sheet in effect on the application submit date will apply, unless a beneficial superseding rate sheet applies, as described under “Rate Sheet Comparison Process.”

If these Rate Sheet Eligibility Conditions are not met, we will cancel the application and return your Purchase Payment.

Application Information Submitted without a Purchase Payment

If you plan to pay the initial Purchase Payment with proceeds from a IRC Section 1035 exchange or direct transfer, your transfer form(s) and application information must be in Good Order within 10 Business Days after the application submit date. In addition, the initial purchase payment necessary to issue the Contract must be received within 90 calendar days after the application submit date.

If these Rate Sheet Eligibility Conditions are met, and the Contract is issued, the RetirePay Terms in the Rate Sheet on the application submit date will apply, unless a beneficial superseding rate sheet applies, as described under “Rate Sheet Comparison Process.”

If these Rate Sheet Eligibility Conditions are not met, we will inform you and request instructions regarding whether to issue the Contract with the RetirePay Terms in effect under the superseding Rate Sheet or cancel the application.

If you have not provided us with the requested instructions within 2 Business Days after we have received your Purchase Payment, we will return your Purchase Payment to the original source.

The requirement to have the necessary application information in Good Order within 10 Business Days for application information received with a Purchase Payment or without a Purchase Payment includes completion of the broker-dealer suitability review.

Rate Sheet Comparison Process