Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263900
Chunk: 18

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 18
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, whether
voluntarily or involuntarily, then we, as a direct or indirect common equity owner of that subsidiary, will be subject to the prior claims of that subsidiary’s creditors, including trade creditors and preferred equity holders. We may never
receive any amounts from that subsidiary, and, accordingly, the assets of that subsidiary may never be available to make payments on the STRK Stock.

We may not have sufficient funds to pay dividends in cash on the STRK Stock, or we may choose not to pay dividends on the STRK Stock. In addition, regulatory and contractual restrictions may prevent us from declaring or paying dividends.

We expect to fund any dividends paid in cash on the
STRK Stock primarily through additional capital raising activities, including, but not limited to, at-the-market offerings of our class A common stock and our junior

SA-10

preferred stock. However, our ability to declare and pay cash dividends on the STRK Stock will depend on many factors, including the following:

| • |     | our financial condition, including the amount of cash we have on hand; |

| • |     | the amount of cash, if any, generated by our operations and financing activities (including our ability to raise 
 additional capital from the equity capital markets on favorable terms or at all);                                |

| • |     | our anticipated financing needs, including the amounts needed to service our indebtedness or other obligations,                                                                                                                                         
 which may be impacted by our ability to sell equity which is reliant on maintaining effective registration statements, certain market conditions, such as sufficient liquid trading volume for our stock, the market price of our securities, the value 
 of our bitcoin holdings, investor sentiment and the general public perception of bitcoin, our strategy and our value proposition;                                                                                                                       |

| • |     | the degree to which we decide to reinvest any cash generated by our operations or financing activities to fund 
 our future operations;                                                                                         |

| • |     | the ability of our subsidiaries to distribute funds to us; |

| • |     | regulatory restrictions on our ability to pay dividends, including under the Delaware General Corporation Law; |

| • |     | our ability to sell equity securities under existing or new at-the-market offering programs, including this offering; and |

| • |     | contractual restrictions on our ability to pay dividends. |

In addition, subject to a limited exception, as described under the caption “Description of STRK Stock—Regular Dividends,” our board of directors may choose not to declare or pay accumulated dividends