Company: MSTR
Filing Date: 2025-05-01
Form Type: 424B5
Source: 0001193125-25-109950
Chunk: 10

Company: Strategy Inc
Filing Date: 2025-05-01
Form: 424B5
Chunk 10
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 whether or when we will realize any cash proceeds from our contemplated acquisition of bitcoin.                                                 |

| Nasdaq Global Select Market symbol | “MSTR” |

| Risk factors | You should read the “Risk Factors” section of this prospectus supplement beginning on page S-11, the “Risk Factors” and “Risk Factor Updates” sections contained in documents incorporated by reference in this          
 prospectus, and the other information included in, or incorporated by reference into, this prospectus for a discussion of factors to consider carefully before deciding to invest in shares of our class A common stock. |

The number of shares of our class A common stock that will be outstanding immediately after this offering as shown above is based on 253,761,553 shares outstanding as of April 29, 2025. For purposes of this calculation, the number of outstanding shares as of April 29, 2025 is deemed to include shares of class A common stock, if any, that were sold under at-the-marketequity offerings programs or that were to be issued pursuant to options that had been exercised or restricted stock units that have vested, but which in each case were

S-9

pending issuance as of such date. The number of shares outstanding as of April 29, 2025 as used throughout this prospectus supplement, unless otherwise indicated, excludes:

| • |     | 4,411,698 shares of class A common stock issuable upon exercise of stock options outstanding as of April 29, 
 2025 at a weighted average exercise price of $41.00 per share;                                               |

| • |     | 1,134,170 shares of class A common stock issuable upon the vesting of restricted stock units outstanding as of 
 April 29, 2025;                                                                                                |

| • |     | 564,644 shares of class A common stock issuable upon the vesting of performance stock units outstanding as of 
 April 29, 2025;                                                                                               |

| • |     | 2,812,927 and 476,404 additional shares of class A common stock available as of April 29, 2025 for future       
 issuance under our 2023 Equity Incentive Plan, as amended, and 2021 Employee Stock Purchase Plan, respectively; |

| • |     | 19,640,250 shares of class A common stock issuable upon conversion of shares of class B common stock issued and 
 outstanding as of April 29, 2025;                                                                               |