0001104659-21-108882 Sample Contracts

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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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.

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.

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.

NINTH AMENDMENT TO PARTICIPATION AGREEMENT REGARDING RULES 30e-3 AND 498A
Participation Agreement • August 24th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

Massachusetts Mutual Life Insurance Company, C.M. Life Insurance Company, and MML Bay State Life Insurance Company (individually and collectively, the “Company”), MML Series Investment Fund (“MML Trust”), a business trust organized under the laws of the Commonwealth of Massachusetts, and MML Investment Advisers, LLC (the “Adviser”), a Delaware limited liability company, entered into a certain participation agreement dated November 17, 2005 (the “Participation Agreement”). This Amendment (the “Amendment”) to the Participation Agreement is entered into as of June 2, 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”), MML Trust, and the Adviser (collectively, the “Parties”).

JANUS ASPEN SERIES FUND PARTICIPATION AGREEMENT (Service Shares)
Fund Participation Agreement • August 24th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Colorado

THIS AGREEMENT is made this 12th day of July, 2021 between Janus Aspen Series, an open-end management investment company organized as a Delaware statutory 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”).

FIRST AMENDMENT TO
Participation Agreement • August 24th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4

WHEREAS, Massachusetts Mutual Life Insurance Company (“Company”), Waddell & Reed, Inc. (“W&R”), distributor for Ivy Funds Variable Insurance Portfolios, and Ivy Funds Variable Insurance Portfolios (the “Ivy Funds VIP”) entered into said Participation Agreement dated October 25, 2012, (the “Agreement”) ; and

July 12, 2021 Massachusetts Mutual Life Insurance Company Springfield, MA 01111 Attention: Office of the General Counsel Dear Mr. Michalowski:
Administrative Services Agreement • August 24th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Colorado

This letter sets forth the agreement between Massachusetts Mutual Life Insurance Company (the “Company”) and Janus Capital Management LLC (the “Adviser”) concerning certain administrative services.

DISTRIBUTION AND SHAREHOLDER SERVICES AGREEMENT Service Shares of Janus Aspen Series (for Insurance Companies)
Distribution and Shareholder Services Agreement • August 24th, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4 • Colorado

This Distribution and Shareholder Services Agreement (this “Agreement”) is made as of July 12, 2021 by and between Janus Distributors LLC (the “Distributor”), a Delaware limited liability company, Massachusetts Mutual Life Insurance Company, a life insurance company organized under the laws of the Commonwealth of Massachusetts (the “Company”), and MML Strategic Distributors (“MSD”), a Delaware limited liability company.

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