Company: MSTR
Filing Date: 2025-03-10
Form Type: 424B5
Source: 0001193125-25-050408
Chunk: 21

Company: Strategy Inc
Filing Date: 2025-03-10
Form: 424B5
Chunk 21
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 we issue
any dividend senior stock in the future, such dividend senior stock could contain provisions that prohibit us from paying accumulated dividends on the perpetual strike preferred stock or purchasing, redeeming or acquiring the perpetual strike
preferred stock until and unless we first pay accumulated dividends in full on such dividend senior stock. As of December 31, 2024, excluding intercompany indebtedness, and on an as-adjusted basis after
giving effect to the conversion of substantially all of the $1.050 billion in principal amount of our 0.0% Convertible Senior Notes due 2027 and the issuance of $2.0 billion of our 0.0% Convertible Senior Notes due 2030, we had
approximately $8.222 billion in aggregate principal amount of consolidated indebtedness outstanding, all of which would rank senior to the perpetual strike preferred stock, and no dividend senior stock or liquidation senior stock outstanding.

In addition, our subsidiaries have no obligation to pay any amounts on the perpetual strike 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 strike preferred stock.

We may not have sufficient funds to pay dividends in cash on the perpetual strike preferred stock, or we may choose not to pay dividends on the perpetual strike 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 strike preferred stock primarily through additional capital raising activities, including, but
not limited to, at-the-market offerings of our class A common stock and

S-17

perpetual strike preferred stock, including pursuant to this offering. However, our ability to declare and pay cash dividends on the perpetual strike 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);                                |

| • |     | our anticipated financing needs, including the amounts needed to