Company: MSTR
Filing Date: 2025-05-22
Form Type: 424B5
Source: 0001193125-25-124554
Chunk: 39

Company: Strategy Inc
Filing Date: 2025-05-22
Form: 424B5
Chunk 39
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 the avoidance of doubt, payments of regular dividends will be applied in accordance with the last sentence of the fourth paragraph under this “—Regular Dividends—Generally” section. For these purposes, and for the avoidance of doubt, but without limitation, none of the following will constitute a sale of shares of our class A common stock:

| • |     | the issuance or sale of any securities that are convertible into, or exchangeable or exercisable for, class A 
 common stock;                                                                                                 |

| • |     | the issuance of any shares of our class A common stock upon the conversion, exchange or exercise of any 
 securities referred to in the preceding bullet point; and                                               |

| • |     | the issuance or sale of any securities pursuant to a registration statement on Form S-8 (or any successor form). |

For the avoidance of doubt, to the extent we fail to pay any portion of such regular dividend in cash due to the limitations described in the preceding paragraph, such portion of such regular dividend will constitute unpaid regular dividends and will accumulate compounded dividends as described under the fourth paragraph under this “—Regular Dividends—Generally” section. Method of Payment Each declared regular dividend on the perpetual strife preferred stock will be paid in cash. Treatment of Dividends Upon Repurchase Upon Fundamental Change or Redemption If the “fundamental change repurchase date” (as defined below under the caption “—Fundamental Change Permits Preferred Stockholders to Require Us to Repurchase Perpetual Strife Preferred Stock”), or redemption S-30

date of any share of perpetual strife preferred stock to be repurchased or redeemed is after a regular record date for a declared regular dividend on the perpetual strife preferred stock and on or before the next regular dividend payment date, then the holder of such share at the close of business on such regular record date will be entitled, notwithstanding such repurchase or redemption, as applicable, to receive, on or, at our election, before such regular dividend payment date, such declared regular dividend on such share. Except as described in the preceding paragraph, regular dividends on any share of perpetual strife preferred stock will cease to accumulate from and after the fundamental change repurchase date or redemption date, as applicable, for such share. Limitations on Our Ability to Pay Dividends We may not have sufficient cash to pay regular dividends on the perpetual strife preferred stock in cash. In addition, applicable law (including the Delaware General Corporation Law), regulatory authorities and the agreements governing our indebtedness may restrict our ability to pay dividends on