Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263731
Chunk: 3

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 3
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 of proceeds | We intend to use the net proceeds from this offering for general corporate purposes, including the acquisition of bitcoin, paying cash dividends on our outstanding preferred stock, and for working capital. |

| Bitcoin is a highly volatile asset that has traded below $70,000 per bitcoin and above $120,000 per bitcoin in our principal market in the 12 months preceding the date of this Common Stock Annex. Bitcoin does not pay                                  
 interest or other returns and so our ability to generate cash from our bitcoin holdings depends on sales. Future fluctuations in bitcoin trading prices may result in our converting bitcoin purchased with the net proceeds from the offering of class A 
 common stock under this Common Stock Annex into cash with a value substantially below the net proceeds from this offering, and there can be no assurance as to whether or when we will realize any cash proceeds from our contemplated acquisition of     
 bitcoin.                                                                                                                                                                                                                                                  |

| See “Use of Proceeds” on page SA-6 of this Common Stock Annex. |

| Nasdaq Global Select Market symbol | “MSTR” |

The number of shares of our class A common stock that will be outstanding immediately after this offering as shown above is based on 267,713,485 shares of class A common stock outstanding as of October 31, 2025. For purposes of this calculation, the number of outstanding shares as of October 31, 2025, is deemed to include shares of class A common stock, if any, that were sold under at-the-marketequity offerings programs or that

SA-1

were to be issued pursuant to options that had been exercised or restricted stock units that have vested, but which in each case were pending issuance as of such date. The number of shares outstanding as of October 31, 2025, as used throughout this Common Stock Annex, unless otherwise indicated, excludes:

| • |     | 3,726,959 shares of class A common stock issuable upon exercise of stock options outstanding as of 
 October 31, 2025, at a weighted average exercise price of $42.36 per share;                        |

| • |     | 806,624 shares of class A common stock issuable upon the vesting of restricted stock units outstanding as of 
 October 31, 2025;                                                                                            |

| • |     | 558,528 shares of class A common stock issuable upon the vesting of performance stock units outstanding as of 
 October 31, 2025;                                                                                             |

| • |     |