Company: MSTR
Filing Date: 2025-07-07
Form Type: 424B5
Source: 0001193125-25-155880
Chunk: 83

Company: Strategy Inc
Filing Date: 2025-07-07
Form: 424B5
Chunk 83
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 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;                                                                        |

| • |     | the conditional conversion feature of the outstanding convertible notes, if triggered, may adversely affect our 
 financial condition and operating results; and                                                                  |

Other Risks

| • |     | the other risks detailed in the “Risk Factors” sections incorporated by reference in this prospectus or 
 contained or incorporated by reference in any prospectus supplement.                                    |

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 may not in fact occur. The forward-looking statements made in this prospectus 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. -7-

RISK FACTORS

Investing in our securities involves significant risks. Before you make a decision to buy our securities, you should carefully review and
consider the specific risks set forth under (i) the caption “Risk Factors” in any applicable prospectus supplement or free writing prospectus and (ii) under the caption “Risk Factors” in our filings with the SEC
pursuant to Sections 13(a), 13(c), 14 or 15(d) of the Exchange Act, incorporated by reference herein and/or included in any prospectus supplement, as well as the risks and uncertainties discussed above under “Cautionary Note Regarding
Forward-Looking Statements”. Additionally, the risks and uncertainties discussed in this prospectus or in any document incorporated by reference into this prospectus are not the only risks and uncertainties that we face, and our business,
financial condition, cash flows, liquidity and results of operations and the market price of the securities we may sell could be materially adversely affected by other matters that are not known to us or that we currently do not consider to be