Massachusetts Mutual Variable Annuity Separate Account 4 Sample Contracts

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Participation Agreement • June 4th, 1998 • Massachusetts Mutual Variable Annuity Separate Account 4 • Massachusetts
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AMENDED AND RESTATED PARTICIPATION AGREEMENT Among VARIABLE INSURANCE PRODUCTS FUNDS, VARIABLE INSURANCE PRODUCTS FUND II, VARIABLE INSURANCE PRODUCTS FUND III, VARIABLE INSURANCE PRODUCTS FUND IV, and VARIABLE INSURANCE PRODUCTS FUND V, FIDELITY...
Participation Agreement • April 24th, 2018 • Massachusetts Mutual Variable Annuity Separate Account 4 • Massachusetts

THIS AMENDED AND RESTATED AGREEMENT, made and entered into as of the 22nd day of May, 2017 by and among MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, (hereinafter the “Company”), a Massachusetts corporation, on its own behalf and on behalf of each segregated asset account of the Company set forth on Schedule A hereto as may be amended from time to time (each such account hereinafter referred to as the “Account”); and FIDELITY DISTRIBUTORS CORPORATION (hereinafter the “Underwriter”), a Massachusetts corporation; and each of VARIABLE INSURANCE PRODUCTS FUND, VARIABLE INSURANCE PRODUCTS FUND II, VARIABLE INSURANCE PRODUCTS FUND III and VARIABLE INSURANCE PRODUCTS FUND IV and VARIABLE INSURANCE PRODUCTS FUND V each an unincorporated business trust organized under the laws of the Commonwealth of Massachusetts (each referred to hereinafter as the “Fund”).

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FUND PARTICIPATION AGREEMENT [ABC Insurance Company] Columbia Funds Variable Insurance Trust Columbia Funds Variable Series Trust II Columbia Management Investment Advisers, LLC and Columbia Management Investment Distributors, Inc.
Fund Participation Agreement • April 25th, 2024 • Massachusetts Mutual Variable Annuity Separate Account 4 • Massachusetts

THIS AGREEMENT, made and entered into as of this ___ day of _______, 2021, by and among [ABC INSURANCE COMPANY] (the “Company”), a [__________] life insurance company, on its own behalf and on behalf of its separate accounts (the “Accounts”); COLUMBIA FUNDS VARIABLE INSURANCE TRUST and COLUMBIA FUNDS VARIABLE SERIES TRUST II, both open-end management investment companies organized under the laws of the Commonwealth of Massachusetts (each a “Fund”); COLUMBIA MANAGEMENT INVESTMENT ADVISERS, LLC (the “Adviser”), a Minnesota limited liability company; and COLUMBIA MANAGEMENT INVESTMENT DISTRIBUTORS, INC. (the “Distributor”), a Delaware corporation.

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PARTICIPATION AGREEMENT BY AND AMONG AIM VARIABLE INSURANCE FUNDS, A I M DISTRIBUTORS, INC., AND MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, ON BEHALF OF ITSELF AND ITS SEPARATE ACCOUNTS.
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Delaware

THIS AGREEMENT, made and entered into as of the 30th day of April, 2004 (“Agreement”), by and among AIM VARIABLE INSURANCE FUNDS, a Delaware Trust (“AVIF”), A I M Distributors, Inc., a Delaware corporation (“AIM”), and MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, a Massachusetts life insurance company (“LIFE COMPANY”), on behalf of itself and each of its segregated asset accounts listed in Schedule A hereto, as the parties hereto may amend from time to time (each, an “Account,” and collectively, the “Accounts”); and (collectively, the “Parties”).

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PARTICIPATION AGREEMENT Massachusetts Mutual Life Insurance Company
Participation Agreement • August 24th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Kansas

This Participation Agreement (“Agreement”), dated as of the 25 day of October, 2012, is made by and between MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY (“Company”), on behalf of itself and each of the separate accounts (“Variable Accounts”), WADDELL & REED, INC. (“W&R”), distributor for Ivy Funds Variable Insurance Portfolios, and IVY FUNDS VARIABLE INSURANCE PORTFOLIOS (“Ivy Funds VIP”).

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FORM OF FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 25th, 2023 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AGREEMENT is effective as of ___________ ____, 2023 (the “Effective Date”), by and among World Funds Trust, an open-end management investment company (the “Fund”), Foreside Fund Services, LLC (“DIST” or the “Underwriter”), a broker-dealer registered as such under the Securities Exchange Act of 1934, as amended (the “1934 Act”), Massachusetts Mutual Life Insurance Company, a life insurance company organized under the laws of Massachusetts (“MassMutual”), and C.M. Life Insurance Company, a life insurance company organized under the laws of Connecticut (“C.M. Life” and together with MassMutual, the “Company”), on its own behalf and on behalf of each separate account of the Company set forth on Schedule A, as may be amended from time to time (each separate account hereinafter referred to individually as an “Account” and collectively as the “Accounts”).

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Exhibit 8(iii) SHAREHOLDER SERVICES AGREEMENT THIS SHAREHOLDER SERVICES AGREEMENT is made and entered into as of , 1998 by and among MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY ("Mass Mutual") and C.M. LIFE INSURANCE COMPANY ("C.M. Life," and...
Shareholder Services Agreement • June 4th, 1998 • Massachusetts Mutual Variable Annuity Separate Account 4
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PARTICIPATION AGREEMENT Among MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, and and PIMCO VARIABLE INSURANCE TRUST, and ALLIANZ GLOBAL INVESTORS DISTRIBUTORS LLC
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • California

THIS AGREEMENT, dated as of the 21st day of April, 2006, by and among Massachusetts Mutual Life Insurance Company, a Massachusetts Life Insurance Company, and C.M. Life Insurance Company, a Connecticut Life insurance company (the “Companies”), on their own behalf and on behalf of their respective separate accounts set forth on Schedule A hereto as may be amended from time to time (each account thereinafter referred to as the “Account”), PIMCO Variable Insurance Trust (the “Fund”), a Delaware statutory trust, and Allianz Global Investors Distributors LLC ( the “Underwriter”), a Delaware limited liability company.

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SHAREHOLDER INFORMATION AGREEMENT
Shareholder Information Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Massachusetts

SHAREHOLDER INFORMATION AGREEMENT entered into as of March 12, 2007 by and between MML Series Investment Fund I (the “Fund”) and Massachusetts Mutual Life Insurance Company, MML Bay State Life Insurance Company and C.M. Life Insurance Company (each an “Intermediary”) with an effective date of October 16, 2007.

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AMENDMENT TO PARTICIPATION AGREEMENT REGARDING RULES 30e-3 AND 498A (Service Shares)
Participation Agreement • April 28th, 2022 • Massachusetts Mutual Variable Annuity Separate Account 4

Massachusetts Mutual Life Insurance Company (the “Company”) and Janus Aspen Series, an open-end management investment company organized as a Delaware business trust (the “Trust”), entered into a certain fund participation agreement dated March 14, 2002, as amended (the “Participation Agreement”). This Amendment (the “Amendment”) to the Participation Agreement is entered into as of March 25, 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”) and the Trust (collectively, the “Parties”).

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SHAREHOLDER INFORMATION AGREEMENT (VUL Product)
Shareholder Information Agreement • August 24th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Massachusetts

SHAREHOLDER INFORMATION AGREEMENT entered into as of April 10, 2007 by and between Janus Aspen Series (the “Fund”) and Massachusetts Mutual Life Insurance Company, and C.M. Life Insurance Company (each an “Intermediary”) with an effective date of October 16, 2007.

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INSURANCE PRODUCTS DISTRIBUTION AGREEMENT
Insurance Products Distribution Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Massachusetts

Principal Underwriter: MML Strategic Distributors, LLC (“MSD”), principal underwriter for the purpose of contracting with duly licensed and registered broker-dealers to distribute variable life insurance and variable annuities; and

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Amended and Restated Rule 22c-2 Agreement
Rule 22c-2 Agreement • August 24th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

This Amended and Restated Rule 22c-2 Agreement (“Agreement”) dated November _13_, 2012 is entered into by and among Waddell & Reed, Inc. (“Distributor”), as principal underwriter for the Ivy Funds Variable Insurance Portfolios (the “Trust”), and the intermediary firm which is a signatory to this Agreement below (the “Intermediary”), effective as of October 25, 2012.

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FORM OF AMENDMENT NO. 1 TO INVESCO FUNDS INTERMEDIARY AGREEMENT REGARDING COMPLIANCE WITH SEC RULE 22c-2
Invesco Funds Intermediary Agreement Regarding Compliance With Sec Rule 22c-2 • April 28th, 2020 • Massachusetts Mutual Variable Annuity Separate Account 4

This Amendment No. 1 to the Invesco Funds Intermediary Agreement Regarding Compliance with SEC Rule 22c-2 is made as of the ___ day of ______________, 2019 by and among Massachusetts Mutual Life Insurance Company, a Massachusetts mutual life insurance company (“MassMutual”), C.M. Life Insurance Company (“C.M. Life”), MML Bay State Life Insurance Company (“MML Bay State”), each a Connecticut life insurance company (together, the “Intermediaries”), and Invesco Investment Services, Inc., a Delaware corporation (“ Invesco”).

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PARTICIPATION AGREEMENT among and MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY and and
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Massachusetts

THIS AGREEMENT, made and entered into as of this 17th day of November, 2005, by and among Massachusetts Mutual Life Insurance Company (“MassMutual”), MML Bay State Life Insurance Company and C.M. Life Insurance Company (each a “Company” and together, the “Companies”), each on their own behalf and on behalf of each segregated asset account of each Company set forth on Schedule A hereto as may be amended from time to time (each such account hereinafter referred to as the “Account”); and MML Series Investment Fund (“MML Trust”), an unincorporated business trust organized under the laws of the Commonwealth of Massachusetts.

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SIXTH AMENDMENT TO PARTICIPATION AGREEMENT Among And MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY And And
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT dated August 28, 2012 amends the Participation Agreement entered into as of the 17th day of November, 2005, as amended to date, (the “Agreement”) by and among Massachusetts Mutual Life Insurance Company, MML Bay State Life Insurance Company, C.M. Life Insurance Company, each on their own behalf and on behalf of each segregated asset account of each insurance company, and MML Series Investment Fund II.

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AMENDMENT NO. 2 TO PARTICIPATION AGREEMENT
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

The Participation Agreement (the “Agreement”), dated as of April 30, 2004, as amended, by and among AIM Variable Insurance Funds, a Delaware trust; Invesco Aim Distributors, Inc., a Delaware corporation; and Massachusetts Mutual Life Insurance Company, a Massachusetts life insurance company, is hereby amended as follows:

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FIRST AMENDMENT TO PARTICIPATION AGREEMENT among and MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY and and AND C.M. LIFE INSURANCE COMPANY
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

The Participation Agreement made and entered into as of the 17th day of November, 2005 by and among Massachusetts Mutual life Insurance Company (“MassMutual”), MML Bay State Life Insurance Company and C.M. Life Insurance Company, each on their own behalf and on behalf of each segregated asset account of each Company, and MML Series Investment Fund (“MML Trust”) is hereby amended as follows:

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FIFTH AMENDMENT TO PARTICIPATION AGREEMENT Among And MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY And And
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT dated August 1, 2011 amends the Participation Agreement entered into as of the 17th day of November, 2005, as amended to date, (the “Agreement”) by and among Massachusetts Mutual Life Insurance Company, MML Bay State Life Insurance Company, C.M. Life Insurance Company, each on their own behalf and on behalf of each segregated asset account of each insurance company, and MML Series Investment Fund II.

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SIXTH AMENDMENT TO PARTICIPATION AGREEMENT Among And And MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY And And
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT dated April 1, 2014 amends the Participation Agreement entered into as of the 17th day of November, 2005, as amended to date, (the “Agreement”) by and among Massachusetts Mutual Life Insurance Company (“MassMutual”), MML Bay State Life Insurance Company, C.M. Life Insurance Company, each on their own behalf and on behalf of each segregated asset account of each insurance company, and MML Series Investment Fund (“MML Trust”).

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SECOND AMENDMENT TO PARTICIPATION AGREEMENT Among And MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY And And
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT dated August 26, 2008 amends the Participation Agreement entered into as of 17th day of November, 2005, as amended to date, (the “Agreement”) by and among Massachusetts Mutual Life Insurance Company, MML Bay State Life Insurance Company, C.M. Life Insurance Company, each on their own behalf and on behalf of each segregated asset account of each insurance company, and MML Series Investment Fund.

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AMENDMENT TO PARTICIPATION AGREEMENT
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

This Amendment to the Participation Agreement dated April 26, 2006, as amended, between ING Investors Trust (“Trust”), ING Funds Distributor, LLC (“Distributor”) and Massachusetts Mutual Life Insurance Company (“Company”) (“Agreement”), is made and entered into this 27th day of May, 2010. All capitalized terms used herein and not otherwise defined shall have the meaning ascribed to such term in the Agreement.

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THIRD AMENDMENT TO PARTICIPATION AGREEMENT Among And MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY And And
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT dated April 9, 2010 amends the Participation Agreement entered into as of 17th day of November, 2005, as amended to date, (the “Agreement”) by and among Massachusetts Mutual Life Insurance Company, MML Bay State Life Insurance Company, C.M. Life Insurance Company, each on their own behalf and on behalf of each segregated asset account of each insurance company, and MML Series Investment Fund.

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AMENDMENT NO. 1 TO PARTICIPATION AGREEMENT
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT is effective as of June 30, 2008. It amends the Participation Agreement dated as of the 21st day of April, 2006 (the “Agreement”) by and among Massachusetts Mutual Life Insurance Company on its own behalf and on behalf of its segregated asset accounts, C.M. Life Insurance Company on its own behalf and on behalf of its segregated asset accounts, PIMCO Variable Insurance Trust, and Allianz Global Investors Distributors LLC.

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EIGHTH AMENDMENT TO PARTICIPATION AGREEMENT Among And And MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY And And
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT dated April 1, 2014 amends the Participation Agreement entered into as of the 17th day of November, 2005, as amended to date, (the “Agreement”) by and among Massachusetts Mutual Life Insurance Company (“MassMutual”), MML Bay State Life Insurance Company, C.M. Life Insurance Company, each on their own behalf and on behalf of each segregated asset account of each insurance company, and MML Series Investment Fund II (“MML II Trust”).

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MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY Springfield, MA 01111-0001
Annuity Contract • September 8th, 2015 • Massachusetts Mutual Variable Annuity Separate Account 4

This Contract was approved under the authority of the Interstate Insurance Product Regulation Commission, hereafter referred to as “Commission” and issued under the Commission’s standards. Any Contract provision that on the provision’s effective date is in conflict with the applicable Commission standards for this product type in effect as of the provision’s effective date of Commission contract approval is hereby amended to conform to the Commission standards in effect as of the provision’s effective date of Commission contract approval.

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AMENDMENT NO. 1 TO PARTICIPATION AGREEMENT
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

The Participation Agreement (the “Agreement”), dated as of April 30, 2004, as amended, by and among AIM Variable Insurance Funds, a Delaware trust; A I M Distributors, Inc., a Delaware corporation; and Massachusetts Mutual Life Insurance Company, a Massachusetts life insurance company, is hereby amended as follows:

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FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Delaware
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TERMINATION, NEW AGREEMENTS AND AMENDMENTS RELATING TO INTERMEDIARY AGREEMENTS FOR PIMCO VARIABLE INSURANCE TRUST
Termination, New Agreements and Amendments • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS TERMINATION, AGREEMENT AND AMENDMENT is made this 10th day of November, 2010, and effective as of the Effective Date (as defined below), by and among Allianz Global Investors Distributors LLC (“AGID”), PIMCO Investments LLC (“PI”) and Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (together, the “Intermediary”).

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Amendment to Participation Agreement
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

This Amendment (“Amendment”) to that certain Participation Agreement (“Agreement”), dated April 21, 2006, as amended, by and among PIMCO Variable Insurance Trust (the “Fund”), PIMCO Investments LLC (the “Underwriter”) and Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (together, the “Company”) is effective this 1st day of May, 2011.

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FOURTH AMENDMENT TO PARTICIPATION AGREEMENT Among And MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY And And
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

This Amendment dated and effective this 23rd day of July, 2010, amends the Participation Agreement among MML Series Investment Fund (“Trust”) and Massachusetts Mutual Life Insurance Company, MML Bay State Life Insurance Company and C.M. Life Insurance Company (collectively referred to as “Companies”) dated November 17, 2005, as amended,(“Agreement”). All capitalized terms used herein and not otherwise defined shall have the meanings ascribed to such terms in the Agreement.

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AMENDMENT TO PARTICIPATION AGREEMENT ING VARIABLE PRODUCTS TRUST
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT is made the 6th day of September, 2008, by and among Massachusetts Mutual Life Insurance Company (the “Company”), a life insurance company organized under the laws of the Commonwealth of Massachusetts, on its own behalf and on behalf of its Separate Accounts (the “Account(s)”) as listed on the amended Schedule A hereto; ING Variable Products Trust (the “Trust”), an open-end management investment company and business trust organized under the laws of the Commonwealth of Massachusetts, and ING Funds Distributor, LLC (hereinafter the “Distributor”), a Delaware limited liability company (collectively, “the Parties”).

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MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY [1295 State Street Springfield, MA 01111-0001]
Annuity Contract • November 3rd, 2006 • Massachusetts Mutual Variable Annuity Separate Account 4

Massachusetts Mutual Life Insurance Company (referred to as “We, Us and Our”) issued this Contract to the Owner (referred to as “You and Your”) at Our Home Office, [1295 State Street, Springfield, Massachusetts 01111-0001,] on the Issue Date. We issued this Contract in exchange for the Purchase Payment. We will make Annuity Payments in accordance with the provisions of this Contract.

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SEVENTH AMENDMENT TO PARTICIPATION AGREEMENT
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

THIS AMENDMENT dated November 12th, 2012 amends the Participation Agreement entered into as of the 17th day of November, 2005, as amended to date, (the “Agreement”) by and among Massachusetts Mutual Life Insurance Company, MML Bay State Life Insurance Company, C.M. Life Insurance Company, each on their own behalf and on behalf of each segregated asset account of each insurance company, and MML Series Investment Fund II.

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THIS IS A LEGAL CONTRACT BETWEEN YOU AND US READ YOUR CONTRACT CAREFULLY
Deferred Annuity Contract • August 24th, 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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