0001193125-19-222147 Sample Contracts

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Variable Annuity Account • August 15th, 2019

We promise to pay the benefits described by this contract subject to its provisions. We make this promise and issue this contract in consideration of the application for it and the receipt of a Purchase Payment. The Owner and the Beneficiary are as named in the application unless they are changed as provided for in this contract.

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THIRD AMENDMENT to PARTICIPATION AGREEMENT Among MINNESOTA LIFE INSURANCE COMPANY, PIMCO VARIABLE INSURANCE TRUST, and PIMCO INVESTMENTS LLC
Participation Agreement • August 15th, 2019 • Variable Annuity Account

THIS AMENDMENT (“Amendment”) is made as of May 1, 2019 by and among PIMCO Investments LLC (“PI”), PIMCO Variable Insurance Trust (the “Fund”) and Minnesota Life Insurance Company (the “Company”).

FIFTH AMENDMENT TO PARTICIPATION AGREEMENT
Participation Agreement • August 15th, 2019 • Variable Annuity Account

This Fifth Amendment (the “Amendment”) dated May 1, 2019 by and among Putnam Variable Trust (the “Trust”), Putnam Retail Management Limited Partnership (the “Underwriter”), and Minnesota Life Insurance Company (the “Company”).

AMENDMENT NUMBER FOUR TO PARTICIPATION AGREEMENT
Participation Agreement • August 15th, 2019 • Variable Annuity Account

This AMENDMENT NUMBER FOUR TO PARTICIPATION AGREEMENT (the “Amendment”) is made and entered into as of March 28, 2019, by and among MINNESOTA LIFE INSURANCE COMPANY (the “Company”), on its own behalf and on behalf of each separate account of the Company identified in the Participation Agreement (as defined below), THE MORGAN STANLEY VARIABLE INSURANCE FUND, INC. (the “Fund”), formerly, THE UNIVERSAL INSTITUTIONAL FUNDS, INC., MORGAN STANLEY DISTRIBUTION, INC. (the “Underwriter”), and MORGAN STANLEY INVESTMENT MANAGEMENT INC. (the “Adviser”). Capitalized terms used but not defined herein shall have the meanings ascribed to them in the Participation Agreement.

Amendment No. 7 to Fund Participation Agreement
Fund Participation Agreement • August 15th, 2019 • Variable Annuity Account

This Amendment No. 7 to Fund Participation Agreement (the “Amendment”) is dated May 1, 2019, and is entered into by and among Minnesota Life Insurance Company, a Minnesota insurance company (the “Company”), ALPS Variable Investment Trust, a Delaware Statutory Trust (the “Trust” or the “Fund,” and each series of the Trust, as applicable, a “Portfolio” and collectively, the “Portfolios”), ALPS Advisors, Inc. a Colorado corporation, (“AAI”), and ALPS Portfolio Solutions Distributor, Inc. (“APSD”), a Colorado corporation.

AMENDMENT NUMBER THREE TO PARTICIPATION AGREEMENT
Participation Agreement • August 15th, 2019 • Variable Annuity Account

This AMENDMENT NUMBER THREE TO PARTICIPATION AGREEMENT (the “Amendment”) is made and entered into as of this 24 day of April, 2015, by and among MINNESOTA LIFE INSURANCE COMPANY (the “Insurer”), on its own behalf and on behalf of each separate account of the Company (each an “Account”) identified in the Participation Agreement (as defined below), Securian Financial Services, Inc., (“Contracts Distributor”), AllianceBernstein L.P., (“Adviser”), and AllianceBernstein Investments, Inc., (“Distributor”).

AMENDMENT NUMBER FOUR TO PARTICIPATION AGREEMENT
Participation Agreement • August 15th, 2019 • Variable Annuity Account

This AMENDMENT NUMBER FOUR TO PARTICIPATION AGREEMENT (the “Amendment”) is made and entered into as of this 1 day of May, 2019, by and among MINNESOTA LIFE INSURANCE COMPANY (the “Insurer”), on its own behalf and on behalf of each separate account of the Company (each an “Account”) identified in the Participation Agreement (as defined below), Securian Financial Services, Inc., (“Contracts Distributor”), AllianceBernstein L.P., (“Adviser”), and AllianceBernstein Investments, Inc., (“Distributor”).

Enhanced Liquidity Option Rider Minnesota Life Insurance Company [Annuity Services ● A1-9999] ● [400 Robert Street North ● St. Paul, Minnesota 55101-2098] [1-800-362-3141] ● [Fax 651-665-7942] ● [securian.com]
Variable Annuity Account • August 15th, 2019

This rider is attached to and made part of this contract as of the Rider Effective Date. Terms not defined in this rider have the meaning given to them in the contract to which this rider is attached. To the extent any of the provisions contained in this rider are contrary to or inconsistent with those of the contract, the provisions of this rider will control.

Amendment No. 6 to Fund Participation Agreement
Fund Participation Agreement • August 15th, 2019 • Variable Annuity Account

This Amendment No. 6 to Fund Participation Agreement (the “Amendment”) is dated June 14, 2017, and is entered into by and among Minnesota Life Insurance Company, a Minnesota insurance company (the “Company”), ALPS Variable Investment Trust, a Delaware Statutory Trust (the “Trust” or the “Fund,” and each series of the Trust, as applicable, a “Portfolio” and collectively, the “Portfolios”), ALPS Advisors, Inc. a Colorado corporation, (“AAI”), and ALPS Portfolio Solutions Distributor, Inc. (“APSD”), a Colorado corporation.

AMENDMENT No. 1 TO THE FUND PARTICIPATION AGREEMENT
Fund Participation Agreement • August 15th, 2019 • Variable Annuity Account

THIS AMENDMENT No. 1 (the “Amendment”), dated as of May 1, 2019, between Minnesota Life Insurance Company (“Minnesota Life”)), Neuberger Berman Advisers Management Trust (“Trust”) and Neuberger Berman Investment Advisers LLC (“NBIA”) (formerly known as Neuberger Berman Management LLC (“NBM”)), is made to the Fund Participation Agreement, dated September 17, 2007, between Minnesota Life, Trust and NBIA (the “Agreement”). Terms defined in the Agreement are used herein as therein defined.

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