Company: MSTR
Filing Date: 2025-05-22
Form Type: 424B5
Source: 0001193125-25-124554
Chunk: 18

Company: Strategy Inc
Filing Date: 2025-05-22
Form: 424B5
Chunk 18
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 parity stock then outstanding. There may be insufficient remaining assets available to pay the liquidation preference and unpaid accumulated dividends on the perpetual strife preferred stock. As of March 31, 2025, excluding intercompany indebtedness, we had approximately $8.22 billion in aggregate principal amount of consolidated indebtedness outstanding, all of which would rank senior to the perpetual strife preferred stock, and no dividend parity stock or liquidation parity stock outstanding. In addition, our subsidiaries have no obligation to pay any amounts on the perpetual strife preferred stock. If any of our subsidiaries liquidates, dissolves or winds up, 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 perpetual strife preferred stock. We may not have sufficient funds to pay dividends in cash on the perpetual strife preferred stock, or we may choose not to pay dividends on the perpetual strife preferred 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 perpetual strife preferred stock primarily through additional capital raising activities, including, but not limited to, at-the-marketofferings of our class A common stock and our preferred stock. However, our ability to declare and pay cash dividends on the perpetual strife preferred 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);                                |

S-16

| • |     | 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;                                                                                         |

| •