Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263759
Chunk: 3

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 3
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 regular dividends, if any, that will have accrued to, but excluding the fundamental change repurchase date. For the avoidance of doubt, the fundamental change repurchase price will not include payment of any undeclared regular dividends. Our business and an investment in the STRD Stock involve significant risks. These risks are described under the caption “ Risk Factors” beginning on page SA-6of this STRD 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 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 STRD 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 STRD 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 STRD Stock Annex in conjunction with the base prospectus supplement dated November 4, 2025 and the accompanying prospectus dated
January 27, 2025. This STRD Stock Annex contains the specific terms of the STRD Stock and of our at-the-market offering of up to $4,133,799,112.67 of shares our of
STRD Stock and the base prospectus supplement describes the terms applicable to our at-the-market offerings of class A common stock and preferred stock in general. You
should carefully consider, among other things, the matters set forth under “