Updating Summary Prospectus (Form 497VPU)

Supplement dated June 16, 2026

to the Prospectus and Updating Summary Prospectus, each dated April 27, 2026, for:

MassMutual Transitions Select^SM

Issued by Massachusetts Mutual Life Insurance Company

THIS SUPPLEMENT MUST BE READ IN CONJUNCTION WITH YOUR PROSPECTUS.

PLEASE RETAIN THIS SUPPLEMENT FOR FUTURE REFERENCE.

This supplement amends certain information in the above-referenced prospectuses:

Fund Reorganization

On November 13, 2025, the Board of Trustees of Voya Investors Trust approved a proposal to reorganize the VY^® CBRE Global Real Estate Portfolio with and into the VY^® Columbia Real Estate Portfolio (the "Reorganization"). The Reorganization is subject to approval by shareholders of the VY^® CBRE Global Real Estate Portfolio. If approved, the Reorganization is expected to occur on or about July 24, 2026 (the "Reorganization Date"). Upon completion of the Reorganization, shareholders of the VY^® CBRE Global Real Estate Portfolio will receive shares of the corresponding class of the VY^® Columbia Real Estate Portfolio that are equal in value to the shares of the corresponding class of the VY^® CBRE Global Real Estate Portfolio held immediately before the Reorganization, and the VY^® CBRE Global Real Estate Portfolio will be liquidated and cease operations.

At any time before the Reorganization, and subject to the terms of your Contract, you may change your Purchase Payment allocation instructions or transfer Contract Value out of the VY^® CBRE Global Real Estate Sub-Account to another investment option available under your Contract.

After the close of the New York Stock Exchange on the Reorganization Date, we will automatically transfer all Contract Value in the VY^® CBRE Global Real Estate Sub-Account to the VY^® Columbia Real Estate Sub-Account. Your Contract Value in the VY^® Columbia Real Estate Sub-Account immediately after the transfer will equal your Contract Value in the VY^® CBRE Global Real Estate Sub-Account immediately before the transfer. The Reorganization is not expected to be a taxable event for Contract Owners. You are not required to take any action in connection with the Reorganization.

Once the Reorganization occurs, the VY^® CBRE Global Real Estate Sub-Account will no longer be available as an investment option. After the Reorganization, any transaction request received in Good Order that refers to the VY^® CBRE Global Real Estate Sub-Account will be treated as referring to the VY^® Columbia Real Estate Sub-Account.

After the Reorganization, if you have any automatic program elections or purchase payment allocation instructions on file for the VY^® CBRE Global Real Estate Sub-Account, we will treat those elections and instructions as applying to the VY^® Columbia Real Estate Sub-Account.

Appendix B

The following Appendix B replaces the existing Appendix B in your Prospectus:

Appendix B

Custom Allocation Choice

For Contracts applied for on or after May 1, 2009 and issued prior to May 1, 2010 with GMAB, GMIB, or MassMutual Lifetime Payment Plus in effect. If you participate in Custom Allocation Choice you must allocate your Purchase Payments within the minimum and maximum range listed for the Sub-Accounts below. No allocation greater than 25% is allowed in any one Sub-Account.

If you applied for your Contract before May 1, 2009, contact our Service Center or your registered representative for details about ranges, asset classes and investment options.

Custom Allocation Choice is unavailable to Contracts issued on or after May 1, 2010 (see "Transfers and Transfer Programs - Asset Allocation Programs").

If you have questions about this supplement, or other product questions, you may contact your registered representative, visit us online at www.MassMutual.com/contact-us, or call our Service Center at (800) 272-2216 8 a.m.-8 p.m. Eastern Time.

For more information about the funds, read each fund prospectus. Fund prospectuses are available on our website at www.MassMutual.com.