0001104659-21-062367 Sample Contracts

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Deferred Annuity Contract • May 6th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

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.

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MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY [Springfield, MA 01111-0001] RETURN OF PURCHASE PAYMENT DEATH BENEFIT RIDER
Return of Purchase Payment Death Benefit Rider • May 6th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

This rider is attached to and modifies the Contract to which it is attached on the Issue Date shown on the Contract Schedule. In case of a conflict with any provision in the Contract, the provisions of this rider will control. The Contract is modified as follows:

AMENDMENT TO PARTICIPATION AGREEMENT REGARDING RULES 30e-3 AND 498A
Participation Agreement • May 6th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

Massachusetts Mutual Life Insurance Company (the “Company”), a life insurance company organized under the laws of the Commonwealth of Massachusetts, AIM Variable Insurance Funds (Invesco Variable Insurance Funds) (the “Fund”), a Delaware business trust, and Invesco Distributors, Inc. (the “Underwriter”), a Delaware corporation, entered into a certain participation agreement dated April 30, 2004, as amended (the “Participation Agreement”). This Amendment (the “Amendment”) to the Participation Agreement is entered into as of May 3, 2021, by and among the Company, on its own behalf and on behalf of each separate account of the Company as set forth in the Participation Agreement, as may be amended from time to time (individually and collectively the “Accounts”), the Fund and the Underwriter (collectively, the “Parties”).

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