Company: MSTR
Filing Date: 2025-03-10
Form Type: 424B5
Source: 0001193125-25-050408
Chunk: 9

Company: Strategy Inc
Filing Date: 2025-03-10
Form: 424B5
Chunk 9
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 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;                                                                        |

S-5

| • |     | We may not have the ability to raise the funds necessary to settle conversions of our existing convertible notes                                                                                                                                       
 in cash or to repurchase the existing convertible notes for cash upon a fundamental change, or to repurchase existing 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 existing 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;             |

Miscellaneous

| • |     | The risks related to the perpetual strike preferred stock and this offering; and |

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

We caution you that the foregoing list of important factors may not contain all of the material factors that are important to you. In addition, in light of these risks and uncertainties, the matters referred to in the forward-looking statements contained in this prospectus supplement may not in fact occur. The forward-looking statements made in this prospectus supplement relate only to events as of the date on which the statements were made. Except as may be required by law, we undertake no obligation to update our forward-looking statements to reflect events and circumstances after the date on which the statements were made or to reflect the occurrence of unanticipated events. S-6

PROSPECTUS SUPPLEMENT SUMMARY

This summary highlights, and is qualified in its entirety by, the more detailed information contained elsewhere in this prospectus supplement and in the documents incorporated by reference in this prospectus. This summary does not contain all of the information that you should consider before making an investment decision. You should read and carefully consider this entire prospectus, including the documents incorporated by reference in this prospectus, especially the information relating to the risks of investing in the perpetual strike preferred stock provided under “Risk Factors” beginning on page S-17of this prospectus supplement and