Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263746
Chunk: 30

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 30
---
 the manner described above, then the related delay in payment shall be deemed not to constitute a failure to declare or pay regular dividends for purposes of the definition of a “regular dividend non-paymentevent.” Except as described in the next paragraph, the certificate of designations does not require us to declare regular dividends on the STRF Stock, even if funds are legally available for their payment. Accordingly, we may choose not to declare regular dividends on the STRF Stock. See “Risk Factors—Risks Relating to the STRF Stock and This Offering—We may not have sufficient funds to pay dividends in cash on the STRF Stock, or we may choose not to pay dividends on the STRF Stock. In addition, regulatory and contractual restrictions may prevent us from declaring or paying dividends.” If we sell any shares of our class A common stock and/or STRK Stock cash through a registered public offering (including an at-the-marketoffering or follow-onoffering) during the 90 calendar days preceding a regular record date, then we will declare and pay the regular dividend due on the regular dividend payment date immediately after such regular record date (including, for the avoidance of doubt, compounded dividends, if any) to the extent the net proceeds to us of such sale(s) during such 90 calendar days are sufficient to pay such regular dividend. For 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