Company: MSTR
Filing Date: 2025-05-01
Form Type: 424B5
Source: 0001193125-25-109950
Chunk: 9

Company: Strategy Inc
Filing Date: 2025-05-01
Form: 424B5
Chunk 9
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 into, this prospectus.

Strategy, MicroStrategy, Strategy One,
Strategy Auto, Intelligence Everywhere, HyperIntelligence, Strategy Consulting, Strategy Education, Strategy Cloud, Enterprise Semantic Graph, Strategy Services, Strategy Professional Services, Strategy Support, and Intelligent Enterprise are either
trademarks or registered trademarks of MicroStrategy Incorporated d/b/a Strategy and its subsidiaries in the United States and certain other countries. Other product and company names mentioned herein may be the trademarks of their respective
owners.

S-8

THE OFFERING

| Class A common stock offered by us | Shares of our class A common stock having an aggregate offering price of up to $21,000,000,000. |

| Class A common stock to be outstanding immediately after this offering | Up to 308,814,639 shares, assuming sales of $21,000,000,000 shares of our class A common stock in this offering at a price of $381.45 per share, which was the last reported sale price of our class A common stock on The Nasdaq Global Select 
 Market on April 29, 2025. The actual number of shares issued will vary depending on the sales price under this offering.                                                                                                                        |

| As of the date hereof, we have 10,330,000,000 shares of class A common stock authorized for issuance under our Second Restated Certificate of Incorporation (as amended and supplemented to date, the “Certificate of 
 Incorporation”).                                                                                                                                                                                                      |

| Manner of offering | “At the market” offering that may be made from time to time through the Agents. See “Plan of Distribution” beginning on page S-16 of this prospectus supplement. |

| Use of proceeds | We intend to use the net proceeds from this offering for general corporate purposes, including the acquisition of bitcoin, paying cash dividends on our outstanding preferred stock, and for working capital. See “Use of Proceeds” on page 
 S-14 of this prospectus supplement.                                                                                                                                                                                                         |

| Bitcoin is a highly volatile asset that has traded below $50,000 per bitcoin and above $105,000 per bitcoin in our principal market in the 12 months preceding the date of this prospectus supplement. Bitcoin does not pay                               
 interest or other returns and so our ability to generate cash from our bitcoin holdings depends on sales. Future fluctuations in bitcoin trading prices may result in our converting bitcoin purchased with the net proceeds from this offering into cash 
 with a value substantially below the net proceeds from this offering, and there can be no assurance as to