Variable Annuity Account Sample Contracts

Among
Participation Agreement • April 29th, 2003 • Variable Annuity Account • New York

THIS AGREEMENT (the "Agreement"), made and entered into as of the 1st day of May, 2002 by and among Minnesota Life Insurance Company (hereinafter the "Company"), on its own behalf and on behalf of each separate account of the Company named in Schedule 1 to this Agreement, as may be amended from time to time by mutual consent (hereinafter collectively the "Accounts"), Oppenheimer Variable Account Funds (hereinafter the "Fund") and OppenheimerFunds, Inc. (hereinafter the "Adviser").

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FOURTH AMENDMENT TO PARTICIPATION AGREEMENT
Participation Agreement • April 27th, 2015 • Variable Annuity Account
Among
Participation Agreement • April 29th, 2003 • Variable Annuity Account • New York
RECITALS
Shareholder Services Agreement • October 4th, 2007 • Variable Annuity Account
AMONG
Participation Agreement • April 27th, 2015 • Variable Annuity Account • Delaware
Ex.99-8b(vii) AMENDMENT NUMBER SEVEN TO THE
Fund Participation Agreement • October 4th, 2007 • Variable Annuity Account
PARTICIPATION AGREEMENT Among and MINNESOTA LIFE INSURANCE COMPANY
Participation Agreement • April 27th, 2023 • Variable Annuity Account • Maryland

THIS AGREEMENT, made and entered into as of this 6 day of April, 2022 by and among Minnesota Life Insurance Company (hereinafter, the “Company”), an insurance company, on its own behalf and on behalf of each segregated asset account of the Company (each account hereinafter referred to as the “Account”), and the undersigned funds, each, a corporation organized under the laws of Maryland (each hereinafter referred to as the “Fund”) and T. Rowe Price Investment Services, Inc. (hereinafter the “Underwriter”), a Maryland corporation.

AMONG
Participation Agreement • April 25th, 2011 • Variable Annuity Account • California
WITNESSETH:
Shareholder Information Agreement • September 6th, 2007 • Variable Annuity Account
AMONG
Participation Agreement • September 30th, 2014 • Variable Annuity Account • Minnesota
MINNESOTA LIFE ENDORSEMENT _______________________________________________________________________________ This endorsement, when attached to the contract, modifies certain contract provisions so as to change the contract to a Single Payment Immediate...
Endorsement • May 21st, 1999 • Variable Annuity Account

This endorsement, when attached to the contract, modifies certain contract provisions so as to change the contract to a Single Payment Immediate Annuity.

AMONG
Participation Agreement • October 4th, 2007 • Variable Annuity Account • Delaware
WITNESSETH:
Investment Accounting Agreement • February 26th, 2003 • Variable Annuity Account • Massachusetts
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CITY, STATE, ZIP -------------------------------------------------------------- --------------------------------------------------------------------- BENEFICIARY CLASS NAME RELATIONSHIP DATE OF BIRTH SEX SOCIAL SECURITY NUMBER / /M / /F...
Variable Annuity Application • May 21st, 1999 • Variable Annuity Account

---------------------------------------------------------------------------------------------------------------- # of Dependents RISK TOLERANCE: (CHECK ONE) TIME HORIZON / / 9-11yrs / / Conservative / / Moderate / / Aggressive / / < 3 yrs / / 4-8 yrs / / 12+ yrs ---------------------------------------------------------------------------------------------------------------- PRIOR INVESTMENT EXPERIENCE / / Mutual Funds / / Limited Partnerships / / Bonds / / Years of Experience / / Annuities / / Stocks / / Options/Futures ----------------------------------------------------------------------------------------------------------------------------------- OWNER/ANNUITANT - I/we represent that the statements and answers in this application are full, complete and true to the SIGNATURES best of my/our knowledge. I/we agree that they are to be considered the basis of any contract issued to me/us. I/we have read and agree with applicable statements.

FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • April 28th, 2021 • Variable Annuity Account • Delaware

THIS AGREEMENT is effective as of 05/01/2021 (the “Effective Date”), by and among each of BLACKROCK VARIABLE SERIES FUNDS, INC. AND BLACKROCK VARIABLE SERIES FUNDS II, Inc., each an open-end management investment company (each, the “Fund”), BLACKROCK INVESTMENTS, LLC (“BRIL” or the “Underwriter”), a broker-dealer registered as such under the Securities Exchange Act of 1934, as amended (the “1934 Act”), and MINNESOTA LIFE INSURANCE COMPANY, a life insurance company organized under the laws of the state of Minnesota (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”).

WITNESSETH:
Business Agreement • April 25th, 2011 • Variable Annuity Account • New York
MFS Fund Distributors, Inc. 500 Boylston Street, Boston, MA 02116-3741 800.343.2829 mfs.com September 1, 2010
Participation Agreement • April 25th, 2011 • Variable Annuity Account

Reference is hereby made to the Participation Agreement by and among the Trust, Minnesota Life Insurance Company (the "Company"), and Massachusetts Financial Services Company dated March 28, 2002 (the "Participation Agreement"). The purpose of this Letter Agreement is to confirm certain financial arrangements between MFS Fund Distributors, Inc. ("MFD"), the underwriter to the Trust, and the Company in connection with the Company's investment in the Trust on behalf of certain separate accounts, as listed in Schedule A of the Participation Agreement.

AMONG
Participation Agreement • September 7th, 2011 • Variable Annuity Account

THIS JOINDER TO PARTICIPATION AGREEMENT ("Joinder") is entered into by MFS Variable Insurance Trust II, a Massachusetts business trust ("Trust II"), MFS Variable Insurance Trust, a Massachusetts business trust ("Trust I"), Massachusetts Financial Services Company, a Delaware corporation ("MFS"), and Minnesota Life Insurance Company, a Minnesota corporation (the "Company"), for the purpose of amending the Participation Agreement dated March 28, 2002 by and among the Company, Trust I, and MFS (the "Agreement"), as amended, to add Trust II as a party thereto as of the date hereof. All references in the Agreement to the "Trust" shall be deemed to refer severally to Trust I and Trust II.

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