Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263900
Chunk: 4

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 4
---
 on which we send the related redemption notice), plus accumulated and unpaid regular dividends to, but excluding, the redemption date.

If a “fundamental change” (as defined in this STRK Stock Annex) occurs, then, except as described in this STRK Stock Annex, preferred stockholders
will have the right (which we refer to as the “fundamental change repurchase right”) to require us to repurchase some or all of their shares of STRK Stock at a cash repurchase

price equal to the liquidation preference (or, upon ratification of the STRK Amendment, the stated amount) of the STRK Stock to be repurchased, plus accumulated and unpaid regular dividends, if any, to, but excluding the fundamental change repurchase date. Our business and an investment in the STRK Stock involve significant risks. These risks are described under the caption “ Risk Factors” beginning on page SA-10of this STRK Stock Annex, under the caption “Risk Factors,” “Risk Factors Related to the ATM Offering Programs” and “Risk Factor Updates” in the accompanying base prospectus supplement dated November 4, 2025 and prospectus and in the documents incorporated by reference into the accompanying base prospectus supplement dated November 4, 2025 and prospectus. Neither the Securities and Exchange Commission nor any state or foreign securities commission or regulatory authority has approved or disapproved of these securities or passed upon the adequacy or accuracy of this STRK Stock Annex, the accompanying base prospectus supplement dated November 4, 2025 or the prospectus. Any representation to the contrary is a criminal offense. We expect to deliver the STRK Stock in book-entry form only through the facilities of The Depository Trust Company on or about the next trading day following the date of purchase.

| TD Securities         |     | Barclays                |     | The Benchmark Company |     | BTIG                     |
| Canaccord Genuity     |     | Cantor                  |     | Clear Street          |     | Compass Point            |
| H.C. Wainwright & Co. |     | Keefe, Bruyette & Woods 
 A Stifel Company        |     | Maxim Group LLC       |     | Mizuho                   |
| Morgan Stanley        |     | Santander               |     | SOCIETE GENERALE      |     | Texas Capital Securities |

November 4, 2025

ADDITIONAL DOCUMENTS RELATED TO THE OFFERING

You should read this STRK Stock Annex in conjunction with the base