MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY Springfield, MA 01111-0001Annuity Contract • December 3rd, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4
This Contract is issued by the Company at its Home Office, 1295 State Street, Springfield, Massachusetts 01111-0001, on the Issue Date. The Contract is issued in exchange for the payment of the initial Purchase Payment.
MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY Springfield, MA 01111-0001Annuity Contract • December 3rd, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4
This Contract is issued by the Company at its Home Office, 1295 State Street, Springfield, Massachusetts 01111-0001, on the Issue Date. The Contract is issued in exchange for the payment of the initial Purchase Payment.
AMENDMENT NO. 4 TO THE SERVICES AGREEMENT AMONG MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY,Services Agreement • December 3rd, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4
THIS AMENDMENT, made and entered into as of the 20th day of October, 2021, amends the Services Agreement entered into as of the 25h day of October, 2012, as amended (the “Agreement”) by and among MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, a life insurance company organized under the laws of the Commonwealth of Massachusetts (the “Company”), MML DISTRIBUTORS, LLC (“MMLD”), MML INVESTOR SERVICES, LLC (“MMLIS”), MML STRATEGIC DISTRIBUTORS, LLC (“MSD”), and IVY DISTRIBUTORS, INC. (“IDI).
SIXTH AMENDMENT TO PARTICIPATION AGREEMENT REGARDING RULES 30e-3 AND 498AParticipation Agreement • December 3rd, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4
Massachusetts Mutual Life Insurance Company (the “Company”), Delaware Ivy Variable Insurance Portfolios (“Delaware Ivy VIP”), and Delaware Distributors, L.P. (“DDLP”), a Delaware limited partnership, are parties to a participation agreement dated October 25, 2012 (the “Participation Agreement”). This Amendment (the “Amendment”) to the Participation Agreement is effective as of May 1, 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 “Variable Accounts”), Delaware Ivy VIP and DDLP (collectively, the “Parties”).
AMENDMENT NO. 7 TO THE PARTICIPATION AGREEMENT AMONG MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, DELAWARE DISTRIBUTORS, L.P. AND IVY VARIABLE INSURANCE PORTFOLIOSParticipation Agreement • December 3rd, 2021 • Massachusetts Mutual Variable Annuity Separate Account 4
THIS AMENDMENT, made and entered into as of the 20th day of October 2021, amends the Participation Agreement entered into as of the 25h day of October, 2012, as amended (the “Agreement”) by and among MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, a life insurance company organized under the laws of the Commonwealth of Massachusetts (the “Company”), DELAWARE DISTRIBUTORS, L.P. (as the assignee successor to Ivy Distributors, Inc.), distributor for Ivy Variable Insurance Portfolios, and IVY VARIABLE INSURANCE PORTFOLIOS (“Ivy VIP”).
