0001133228-22-002258 Sample Contracts

JANUS ASPEN SERIES FUND PARTICIPATION AGREEMENT (Service Shares)
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • Colorado

THIS AGREEMENT is made this 14 day of March, 2002, between JANUS ASPEN SERIES, an open-end management investment company organized as a Delaware business trust (the “Trust”), and Massachusetts Mutual Life Insurance Company, a life insurance company organized under the laws of the Commonwealth of Massachusetts (the “Company”), on its own behalf and on behalf of each segregated asset account of the Company set forth on Schedule A, as may be amended from time to time (the “Accounts”).

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PARTICIPATION AGREEMENT
Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • Delaware

THIS AGREEMENT, made mad entered into this day of , 1998 by and between GOLDMAN SACHS VARIABLE INSURANCE TRUST, an unincorporated business trust formed under the laws of Delaware (the “Trust”), GOLDMAN, SACHS & CO., a New York limited partnership (the “Distributor”), and MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, a Massachusetts life insurance company (the “Company”), on its own behalf and on behalf of each separate account of the Company identified herein.

JANUS ASPEN SERIES FUND PARTICIPATION AGREEMENT
Janus Aspen Series • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • Colorado

THIS AGREEMENT is made this 30 day of August, 1999, between JANUS ASPEN SERIES, an open-end management investment company organized as a Delaware business trust (the “Trust”), and MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, a life insurance company organized under the laws of the State of Massachusetts (the “Company”), on its own behalf and on behalf of each segregated asset account of the Company set forth on Schedule A, as may be amended from time to time (the “Accounts”).

SHAREHOLDER INFORMATION AGREEMENT
Shareholder Information Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • Massachusetts

SHAREHOLDER INFORMATION AGREEMENT entered into as of March 12, 2007 by and between DWS Scudder Distributors, Inc. (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.

AMENDMENT TO FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This amendment, dated and effective as of May 1, 2011 (the “Amendment”), amends the Fund Participation Agreement dated as of August 30, 1999, as amended to date, by and between Janus Aspen Series, an open-end management investment company organized as a Delaware statutory trust (the “Trust”) and Massachusetts Mutual Life Insurance Company (the “Company”) (the “Agreement”). All capitalized terms used herein and not otherwise defined shall have the meaning ascribed to such term in the Agreement.

SHAREHOLDER INFORMATION AGREEMENT (VUL Product)
Shareholder Information Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • 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.

AMENDMENT TO PARTICIPATION AGREEMENT AMENDMENT NO. 5
Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This AMENDMENT is effective as of this 6th day of April 2011, by and among GOLDMAN SACHS VARIABLE INSURANCE TRUST, a statutory trust formed under the laws of Delaware (the “Trust”), GOLDMAN, SACHS & CO., a New York limited partnership (the “Distributor”), and MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, a life insurance company organized under the laws of the State of Massachusetts (the “Company”), on its own behalf and on behalf of each separate account of the Company identified in the Participation Agreement (as defined below).

AMENDMENT TO PARTICIPATION AGREEMENT AMENDMENT NO. 4
Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

THIS AGREEMENT made the 23rd day of October 1998, and amended on November 1, 1999, May 1, 2000, April 15, 2001, and May 1, 2003 (the “Participation Agreement”), by and between GOLDMAN SACHS VARIABLE INSURANCE TRUST, an unincorporated business trust formed under the laws of Delaware (the “Trust”), GOLDMAN SACHS & CO., a New York limited partnership (the “Distributor”), MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, a life insurance company organized as a corporation under the laws of the State of Massachusetts (hereinafter referred to as the “Company”), on its own behalf and on behalf of each separate account of the Company identified in the Participation Agreement.

AMENDMENT NO. 3 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This Amendment, dated as of April 30, 2010, to the Fund Participation Agreement dated as of the 7th day of March 2003 (“Agreement”), as amended to date, by and between American Funds Insurance Series (the “Series”), Capital Research and Management Company (”CRMC”), and Massachusetts Mutual Life Insurance Company (the “Company”). All capitalized terms used herein and not otherwise defined shall have the meaning ascribed to such term in the Agreement.

AMENDMENT TO PARTICIPATION AGREEMENT AMENDMENT NO. 3
Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

THIS AGREEMENT made the 23rd day of October 1998, and amended on November 1, 1999 and May 1, 2000 (the “Participation Agreement”), by and between GOLDMAN SACHS VARIABLE INSURANCE TRUST, an unincorporated business trust formed under the laws of Delaware (the “Trust”), GOLDMAN SACHS & CO., a New York limited partnership (the “Distributor”), MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, a life insurance company organized as a corporation under the laws of the State of Massachusetts (hereinafter referred to as the “Company”), on its own behalf and on behalf of each separate account of the Company identified in the Participation Agreement.

FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • Massachusetts

THIS AGREEMENT is entered into as of the 7th day of March, 2003 among Massachusetts Mutual Life Insurance Company, a life insurance company organized under the laws of the Commonwealth of Massachusetts (on behalf of itself and certain of its separate accounts, hereinafter referred to as “MassMutual”); AMERICAN FUNDS INSURANCE SERIES (”Series”), an open-end management investment company organized under the laws of the Commonwealth of Massachusetts, and CAPITAL RESEARCH AND MANAGEMENT COMPANY (”CRMC”), a corporation organized under the laws of the State of Delaware.

DISTRIBUTION AND SHAREHOLDER SERVICES AGREEMENT Service Shares of Janus Aspen Series (for Insurance Companies)
Distribution and Shareholder Services Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • Colorado

This Agreement is made as of March 14, 2002, by and between Janus Distributors, Inc. (the “Distributor”), a Colorado corporation, and Massachusetts Mutual Life Insurance Company (the “Company”), a Massachusetts corporation.

FIRST AMENDMENT TO BUSINESS AGREEMENT
Business Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This First Amendment, effective as of May 1, 2013, is by and among Massachusetts Mutual Life Insurance Company (“MassMutual”); MML Distributors, LLC (the “Distributor”); American Funds Distributors, Inc. (“AFD”); and Capital Research and Management Company (“CRMC”). This Amendment amends the Business Agreement (the “Agreement”) dated the 7th day of March, 2003. All capitalized terms used herein and not otherwise defined shall have the meaning ascribed such terms in the Agreement.

SECOND AMENDMENT TO BUSINESS AGREEMENT
Business Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This Second Amendment, dated as of September 1, 2014, is by and among Massachusetts Mutual Life Insurance Company (“MassMutual”), MML Distributors, LLC (“MMLD”), MML Strategic Distributors, LLC (“MSD”), American Fund Distributors, Inc. (“AFD”), and Capital Research and Management Company (“CRMC”). This Amendment amends the Business Agreement dated March 7, 2003 as amended (the “Agreement”). All capitalized terms used herein and not otherwise defined shall have the meaning ascribed such terms in the Agreement.

AMENDMENT NO 7 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This Amendment to the Participation Agreement among DWS Investments VIT Funds (formerly, Scudder Investments VIT Funds, Deutsche Asset Management VIT Funds and BT Insurance Funds Trust) (“Trust”), Deutsche Investment Management Americas Inc. (successor by merger to Deutsche Asset Management, Inc.) (”Adviser”), and Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (collectively, “Company”) dated September 1, 1999, as amended, (“Agreement”) is dated and effective this 12th day of July, 2010. All capitalized terms used herein and not otherwise defined shall have the meaning ascribed to such term in the Agreement.

AMENDMENT NO. 5 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

AMENDMENT, dated as of August 1, 2004, to the Fund Participation Agreement dated as of the 1st day of September, 1999 (the “Agreement”), by and between Scudder Investments VIT Funds (formerly, Deutsche Asset Management VIT Funds ) (“Trust”), Deutsche Asset Management, Inc. (“Adviser”), Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (collectively the “Life Companies”)

FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • New York

THIS AGREEMENT made as of the 1st day of September, 1999 by and among BT Insurance Funds Trust (“TRUST”), a Massachusetts business trust, Bankers Trust Company (“ADVISER”), a New York banking corporation, and Massachusetts Mutual Life Insurance Company, a life insurance company organized under the laws of The Commonwealth of Massachusetts, and C.M. Life Insurance Company, a life insurance company organized under the laws of the state of Connecticut (collectively the “LIFE COMPANIES”).

BUSINESS AGREEMENT
Business Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I • California

THIS AGREEMENT is entered into as of the 7th day of March, 2003 (the “Effective Date”) by and among Massachusetts Mutual Life Insurance Company, a life insurance company organized under the laws of the Commonwealth of Massachusetts (on behalf of itself and certain of its separate accounts and hereinafter referred to as “MassMutual”); MML Distributors, LLC (the “Distributor”), a limited liability company organized under the laws of the State of Connecticut; AMERICAN FUNDS DISTRIBUTORS, INC. (“AFD”), a corporation organized under the laws of the State of the California; and CAPITOL RESEARCH AND MANAGEMENT COMPANY (“CRMC”), a corporation organized under the laws of the State of Delaware.

AMENDMENT TO FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This Amendment to the Fund Participation Agreement ("Agreement") dated August 30, 1999, as amended, among Janus Aspen Series, an open-end management investment company organized as a Delaware business trust (the "Trust"), and Massachusetts Mutual Life Insurance Company, a Massachusetts life insurance company (the "Company") is effective as of April 15, 2001.

AMENDMENT TO FUND PARTICIPATION AGREEMENT (Service Shares)
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This Amendment to the Fund Participation Agreement dated March 14, 2002, among Janus Aspen Series, an open-end management investment company organized as a Delaware business trust (the “Trust”), and Massachusetts Mutual Life Insurance Company (the “Company”) is effective as of April 1, 2003.

AMENDMENT NO. 2 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

AMENDMENT, dated as of May 1, 2006, to the Fund Participation Agreement dated as of the 7th day of March 2003 and August 1, 2004 (the “Agreement”), by and between American Funds Insurance Series (“Series”), Capital Research and Management Company (“CRMC”), Massachusetts Mutual Life Insurance Company (“MassMutual”).

AMENDMENT NO. 6 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

AMENDMENT, dated as of October 1, 2006, to the Fund Participation Agreement dated as of the 1st day of September, 1999, as amended from time to time (the “Agreement”), by and among DWS Investments VIT Funds (formerly, Scudder Investments VIT Funds and Deutsche Asset Management VIT Funds and BT Insurance Funds Trust) (“Trust”), Deutsche Asset Management, Inc. (“Adviser”), and Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (collectively, “Life Companies”).

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AMENDMENT NO. 4 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

AMENDMENT, dated as of July 8, 2003, to the Fund Participation Agreement dated as of the 1st day of September, 1999 (the “Agreement”), by and between Scudder Investments VIT Funds (formerly, Deutsche Asset Management VIT Funds ) (“Trust”), Deutsche Asset Management, Inc. (“Adviser”), Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (collectively the “Life Companies”)

AMENDMENT NO. 1 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

AMENDMENT, dated as of August 1, 2004, to the Fund Participation Agreement dated as of the 7th day of March 2003 (the “Agreement”), by and between American Funds Insurance Series (“Series”), Capital Research and Management Company (“CRMC”), Massachusetts Mutual Life Insurance Company (“MassMutual”).

AMENDMENT NO. 5 FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This Amendment, dated as of November 18, 2020, amends the Fund Participation Agreement (the “Agreement”), dated the 7th day of March, 2003, as amended, by and a mong Massachusetts Mutual Life Insurance Company (on behalf of itself and certain of its separate accounts, hereinafter referred to as “MassMutual”); American Funds Insurance Series (“Series”); American Funds Service Company (“Transfer Agent”); American Funds Distributors, Inc. (“AFD”), and Capital Research and Management Company (“CRMC”).

AMENDMENT NO. 2 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

AMENDMENT, dated as of January 16, 2001 to the Fund Participation Agreement dated as of September 1, 1999 (the “Agreement”), by and between Deutsche Asset Management VIT Funds (“Trust”), Bankers Trust Company (“Adviser”), Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (collectively, “Life Companies”)

AMENDMENT NO. 1 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

AMENDMENT, dated as of February 1, 2000, to the Fund Participation Agreement dated as of the 1st day of September, 1999 (the “Agreement”), by and between BT Insurance Funds Trust (“Trust”), Bankers Trust Company (“Adviser”) Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (collectively the “Life Companies”).

AMENDMENT NO. 2 TO FUND PARTICIPATION AGREEMENT (Service Shares)
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

This Amendment to the Fund Participation Agreement dated March 14, 2002, among Janus Aspen Series, (the “Trust”), and Massachusetts Mutual Life Insurance Company (the “Company”) is effective as of August 1, 2004.

AMENDMENT NO. 3 to the FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 21st, 2022 • Massachusetts Mutual Variable Life Separate Account I

AMENDMENT, dated as of April 24, 2001, to the Fund Participation Agreement dated as of the 1st day of September, 1999 (the “Agreement”), by and between Deutsche Asset Management VIT Funds (formerly, BT Insurance Funds Trust) (“Trust”), Bankers Trust Company (“Adviser”) Massachusetts Mutual Life Insurance Company and C.M. Life Insurance Company (collectively the “Life Companies”)

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