Company: MSTR
Filing Date: 2025-05-01
Form Type: 424B5
Source: 0001193125-25-109950
Chunk: 6

Company: Strategy Inc
Filing Date: 2025-05-01
Form: 424B5
Chunk 6
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 class A common stock; |

Risks Related to Our Class A Common Stock

| • |     | The market price of our class A common stock has been and may continue to be volatile; |

| • |     | Because of the rights of our two classes of common stock and because Michael J. Saylor, who beneficially owns the                                                                                                                           
 majority of our class B common stock, controls a significant portion of our total voting power, Mr. Saylor has significant influence over matters that require approval of our stockholders and as a result could impede a third party from 
 acquiring us, or limit the ability of our other stockholders to influence corporate matters;                                                                                                                                                |

| • |     | Future sales of securities by us could depress the price of our class A common stock; |

| • |     | Our outstanding series of preferred stock are senior to our class A common stock with respect to liquidation and                            
 dividends, which could result in lower or no payments to the holders of class A common stock upon a liquidation, dissolution or winding up; |

Risks Related to Our Outstanding and Potential Future Indebtedness

| • |     | Our level and terms of indebtedness could adversely affect our ability to raise additional capital to further                         
 execute on our bitcoin strategy, fund our enterprise analytics software operations, and take advantage of new business opportunities; |

| • |     | We may be unable to service our indebtedness, which could cause us to default on our debt obligations and could 
 force us into bankruptcy or liquidation;                                                                        |

| • |     | We may not have the ability to raise the funds necessary to settle conversions of our outstanding convertible                                                                                                                                             
 notes in cash or to repurchase the convertible notes for cash upon a fundamental change, or to repurchase convertible notes if noteholders exercise their repurchase rights, and any future debt may contain limitations on our ability to engage in cash 
 settled conversions or repurchases of convertible notes;                                                                                                                                                                                                  |

| • |     | Despite our current level of indebtedness, we may incur substantially more indebtedness and enter into other 
 transactions in the future which could further exacerbate the risks related to our indebtedness; and         |

Other Risks

| • |     | the other risks detailed in this prospectus supplement and in the “Risk Factors” and “Risk Factor              
 Updates” sections in the accompanying prospectus or in documents incorporated by reference herein and therein. |

S-5

We caution you that the foregoing list of important factors may not contain all of