0000930413-21-001239 Sample Contracts

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 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.

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.

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

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.

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.

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:

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:

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.

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”).

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.

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.

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.

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.

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”).

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:

FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Delaware
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”).

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.

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.

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”).

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

THIS AMENDMENT dated December 23, 2014 and effective as of May 1, 2014 (“Amendment”), amends the Participation Agreement, dated April 26, 2006, as amended, (“Agreement”), by and among Massachusetts Mutual Life Insurance Company (“MMLIC” or 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 ( “Account(s)”) as listed on the amended Schedule A of the Agreement, Voya Investors Trust (formerly known as “ING Investors Trust”) (“Trust”), and Voya Investments Distributor, LLC (formerly known as “ING Investments Distributor, LLC”) (“Distributor”).

Rule 22c-2 Shareholder Information Agreement Related to Variable Insurance Products
Shareholder Information Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

SHAREHOLDER INFORMATION AGREEMENT entered into as of April 5, 2007 by and between the Fidelity Distributors Corporation and Massachusetts Mutual Life Insurance Company, MML Bay State Life Insurance Company and C.M. Life Insurance Company on behalf of an insurance company separate account. (collectively, the “Company”) with an effective date of October 16, 2007.

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 II.

ALLIANZ GLOBAL INVESTORS DISTRIBUTORS LLC Stamford, CT 06902 SELLING AGREEMENT FOR ADVISOR CLASS SHARES OF PIMCO VARIABLE INSURANCE TRUST
Selling Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Delaware

We are the distributor of the Advisor Class shares of those series of PIMCO Variable Insurance Trust set forth in Appendix A (collectively, the “Funds”). Shares are offered pursuant to the then-current prospectus, including any supplements or amendments thereto, of each of the Funds (the “Prospectus”). To the extent that a Prospectus contains provisions that are inconsistent with the terms of this Agreement, the terms of the Prospectus shall be controlling. We have the exclusive right to distribute shares of the Funds (the “Shares”). As agent for the Funds, we hereby offer to sell Shares of the Funds to you, upon the following terms and conditions:

SEVENTH 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 August 11, 2015 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”).

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 II (“MML Trust”) is hereby amended as follows:

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 28th day of May, 2007, 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”).

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 II (“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.

NINTH 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 August 11, 2015 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”).

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

THIS AMENDMENT made the 17th day of January, 2014 amends the Participation Agreement dated April 26, 2006, as amended, by and among Massachusetts Mutual Life Insurance Company (“MMLIC”, or the “Company”), ING Investors Trust (“Trust”), and ING Investments Distributor, LLC (formerly known as “ING Funds Distributor, LLC”) (“Distributor”) (the “Agreement”).

UNDERWRITING AND SERVICING AGREEMENT
Underwriting and Servicing Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Massachusetts

This UNDERWRITING AND SERVICING AGREEMENT is made this 16th day of December, 2014, by and between MML Investors Services, LLC (“MMLIS”) and Massachusetts Mutual Life Insurance Company (“MassMutual”), on its own behalf and on behalf of MassMutual’s variable annuity and variable life separate accounts included on Exhibit A (the “Separate Accounts”), as follows:

RULE 22C-2 AMENDMENT TO PARTICIPATION AGREEMENT
Participation Agreement • June 25th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

AMENDMENT entered into as of April 2, 2007, by and between Allianz Global Investors Distributors LLC (“AGID”), the principal underwriter for PIMCO Variable Insurance Trust (a “Trust”) and Massachusetts Mutual Life Insurance Company, and its subsidiary, C.M. Life Insurance Company (collectively, “the Intermediary”).

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 as of 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 II.

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