Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B2
Source: 0001193125-25-263653
Chunk: 13

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B2
Chunk 13
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 additional convertible debt, convertible preferred stock or other
securities convertible into or exchangeable for our securities, at prices that may not be the same as the price per share that you pay in the offerings of securities under this base prospectus supplement, and investors purchasing shares or other
securities in the future could have rights superior to existing stockholders. Any such future offerings could result in further dilution to you.

S-9

Future sales, or the perception of future sales, of our class A common stock, debt instruments, our convertible or non-convertiblepreferred stock, or other securities could depress the trading price of the securities. We may issue and sell additional notes, shares of class A common stock, convertible debt instruments, convertible or non-convertiblepreferred stock, or other securities in subsequent offerings to raise capital or issue shares for other purposes, including in connection with the acquisition of additional bitcoin. For example, between January 1, 2024 and October 31, 2025, we issued and sold:

| • |     | $1.16 billion of shares of 10.00% Series A Perpetual Strife Preferred Stock, $0.001 par value per share (the 
 “STRF Stock”);                                                                                               |

| • |     | $2.52 billion of shares of Variable Rate Series A Perpetual Stretch Preferred Stock, $0.001 par value per share 
 (the “STRC Stock”);                                                                                             |

| • |     | $1.24 billion of shares of 8.00% Series A Perpetual Strike Preferred Stock, $0.001 par value per share (the 
 “STRK Stock”);                                                                                              |

| • |     | $1.07 billion of shares of 10.00% Series A Perpetual Stride Preferred Stock, $0.001 par value per share (the 
 “STRD Stock”);                                                                                               |

| • |     | $28.28 billion shares of class A common stock through at-the-market equity offering programs; |

| • |     | $800.00 million aggregate principal amount of 0.625% Convertible Senior Notes due 2030 (“2030A 
 Convertible Notes”);                                                                           |

| • |     | $2.00 billion aggregate principal amount of 0% 2030 Convertible Senior Notes due 2030 (“2030B 
 Convertible Notes”);                                                                          |

| • |     | $603.75 million aggregate principal amount