The MassMutual Envision VA, offered by Massachusetts Mutual Life Insurance Company (MassMutual), is designed to help individuals accumulate assets for retirement. MassMutual RetirePay is an optional guaranteed lifetime withdrawal benefit offered with MassMutual Envision VA for an additional cost. It is designed for individuals seeking predictable retirement income that can be counted on regardless of market conditions.

Just like the stability of retirement income offered by RetirePay, the Cboe Vest US Large Cap 10% Buffer Strategies VI fund, offered by Cboe Vest Financial, gives individuals access to an investment tool to potentially hedge equity risk.

“In recent years as market volatility, inflation, interest rates, and overall uncertainty have risen, many near retirees and retirees have become increasingly concerned about their retirement portfolios and want to make sure their retirement assets grow and are protected at the same time,” said Phil Michalowski, head of annuity product with MassMutual. “This buffer fund helps individuals manage portfolio risk with the potential for growth.”

The fund seeks to cushion — or buffer — equity losses in down markets, while allowing participation in potential upside gains to a cap. To do so, the fund invests in a laddered portfolio of one-year buffer strategies, with 10% downside buffers and caps that recalibrate to prevailing levels of the S&P 500 each month.

“We are thrilled to make the buffer fund available in MassMutual’s VA lineup,” said J. Steven Neamtz, head of strategic development with Cboe Vest. “We offer many variations of the buffer strategy to give agents and advisors in insurance, wealth and retirement powerful risk management tools they can use to target specific investment outcomes for their clients. We believe our buffer fund, with its core ‘all-weather’ risk-management strategy, will be a valuable option for MassMutual Envision contract owners.”

About MassMutual

MassMutual is a leading mutual life insurance company that is run for the benefit of its members and participating policy owners. Founded in 1851, the company has been continually guided by one consistent purpose: we help people secure their future and protect the ones they love. With a focus on delivering long-term value, MassMutual offers a wide range of protection, accumulation, wealth management and retirement products and services. For more information, visit www.massmutual.com.

About Cboe Vest

Cboe Vest Financial LLC, a wholly owned subsidiary of Cboe Vest Group Inc., offers institutional-quality Target Outcome Investments® built on the backbone of its unique investment philosophy, that strive to buffer losses, amplify gains, manage volatility, or provide consistent income. In 2012 the Cboe Vest team began designing the methodology (see patent application) and developing the trading infrastructure for buffer strategy-based registered funds, and introduced the first buffer strategy in a registered fund in 2016. For more information, visit cboevest.com.

MassMutual Envision Disclosures:

• MassMutual Envision is not available in New York and certain features and funds may not be available in all states. MassMutual Envision (Contract Form FPVDA21 and ICC21-FPVDA in certain states, including North Carolina) is a flexible premium deferred variable annuity contract issued by Massachusetts Mutual Life Insurance Company, Springfield, MA 01111-0001.

• MassMutual does not recommend or endorse any particular fund, and MassMutual does not provide investment advice. MassMutual Envision contract owners are responsible for choosing the funds, and the amounts allocated to each, that are appropriate for their own individual circumstances and their investment goals, financial situation, and risk tolerance.

• For more information on MassMutual Envision, the optional RetirePay feature, and the risks associated with buffer funds, visit www.massmutual.com/envision and see the “Principal Risks of Investing in the Contract – Defined Outcome Funds Risk” section of the prospectus. For more information on other retirement income options from MassMutual, visit www.massmutual.com/retirement.

• Any guarantees explicitly referenced herein regarding MassMutual Envision are based on the claims paying ability of the issuing insurance company.

• Principal Underwriters: MML Investors Services, LLC, and MML Strategic Distributors, LLC, subsidiaries of Massachusetts Mutual Life Insurance Company, Springfield, MA 01111-0001.

• Variable annuities offered through registered representatives of MML Investors Services, LLC, Springfield, MA 01111-0001 or a broker-dealer that has a selling agreement with MML Strategic Distributors, LLC, Springfield, MA 01111-0001.

Cboe Vest U.S. Large Cap 10% Buffer Strategies VI Fund Disclosures:

• The Cboe Vest U.S. Large Cap 10% Buffer Strategies VI Fund is only available to insurance company separate accounts and qualified retirement plans. It is not available for purchase directly by the general public, and is not the same as other mutual fund portfolios with very similar or nearly identical names and investment goals and policies that are sold directly to the public.

• For more information on Cboe Vest U.S. Large Cap 10% Buffer Strategies VI Fund, visit https://www.cboevest.com/insurance-funds/buffer-10-fund.

• Investors should consider the investment objectives, potential risks, management fees and charges and expenses carefully before investing. This and other information is contained in the Fund’s prospectus, which may be obtained online, or by calling 855-505-VEST (8378). Please read the prospectus carefully before investing. Distributed by Foreside Fund Services, LLC, Portland, ME. Member FINRA/SIPC.

• Investing involves risk. Loss of principal is possible. While Cboe Vest Financial LLC seeks to deliver the returns of the 10% Buffer Strategy for each of the 12 strategies in the laddered portfolio, the strategy may not work as intended. The protection intended by the strategy is not guaranteed, and it is possible to lose more than the targeted 10% buffer. The Fund’s investment strategy is not designed to achieve a specific outcome over a specific holding period. Derivative Securities Risk. The Fund may invest in derivative securities. The Fund could experience a loss if derivatives do not perform as anticipated, or are not correlated with the performance of other investments which are used to hedge, or if the Fund is unable to liquidate a position because of an illiquid secondary market. FLEX Options Risk. The Fund bears the risk that the Options Clearing Corporation (OCC) will be unable or unwilling to perform its obligations under the FLEX Options contracts. Additionally, FLEX Options may be less liquid. Furthermore, the values of FLEX Options do not increase or decrease at the same rate as the Index, which may cause the Fund’s NAV to fluctuate. Please see the prospectus for more information regarding these and other risks associated with the Fund.

• Cboe Vest U.S. Large Cap 10% Buffer Strategies VI Fund is a Target Outcome Fund®. Target Outcome Funds and Target Outcome Investments are registered trademarks of Cboe Vest Financial LLC. Cboe® is a registered trademark of Cboe Exchange, Inc. Cboe Vest^SM is a service mark of Cboe Exchange, Inc.

• S&P 500 Index: The index includes 500 leading companies and captures approximately 80% of available U.S. equity market capitalization.