Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263719
Chunk: 5

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 5
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IG                     |
| 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 STRC Stock Annex in conjunction with the base prospectus supplement dated November 4, 2025 and the accompanying prospectus dated
January 27, 2025. This STRC Stock Annex contains the specific terms of the STRC Stock and of our at-the-market offering of up to $4,200,000,000.00 of shares our of
STRC 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 “Risk Factors Related to the ATM Offering Programs” in the base prospectus supplement and “Risk Factors” in this STRC Stock Annex.

You may access the base prospectus supplement and accompanying prospectus on the SEC website at www.sec.gov as follows (or if such address has changed, by
reviewing our filings for the relevant date on the SEC website): https://www.sec.gov/Archives/edgar/data/1050446/000119312525263653/d87896d424b2.htm

TABLE OF CONTENTS PROSPECTUS SUPPLEMENT STRC STOCK ANNEX

| THE OFFERING                                             |     | SA-1  |
| RISK FACTORS                                             |     | SA-8  |
| USE OF PROCEEDS                                          |     | SA-17 |
| DESCRIPTION OF STRC STOCK                                |     | SA-18 |
| MATERIAL UNITED STATES FEDERAL INCOME TAX CONSIDERATIONS |     | SA-38 |
| PLAN OF DISTRIBUTION                                     |     | SA-46 |
| LEGAL MATTERS                                            |     | SA-47 |

THE OFFERING The summary below describes the principal terms of the offering and the STRC Stock. The summary is qualified in its entirety by reference to the more detailed information appearing elsewhere in this STRC Stock Annex and the accompanying base prospectus supplement