Company: MSTR
Filing Date: 2025-05-22
Form Type: 424B5
Source: 0001193125-25-124554
Chunk: 2

Company: Strategy Inc
Filing Date: 2025-05-22
Form: 424B5
Chunk 2
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 number of shares of perpetual strife preferred stock that have been issued in all offerings we have made of perpetual strife preferred stock as of such date, taken together. In addition, we have the right to redeem all, but not less than all, of the perpetual strife preferred stock if a “tax event” (as defined in this prospectus supplement) occurs. The redemption price for any perpetual strife preferred stock to be redeemed will be a cash amount equal to the liquidation preference of the perpetual strife preferred stock to be redeemed as of the business day before the date we send the related redemption notice, plus accumulated and unpaid regular dividends to, but excluding, the redemption date. If a “fundamental change” (as defined in this prospectus supplement) occurs, then, except as described in this prospectus supplement, preferred stockholders will have the right (which we refer to as the “fundamental change repurchase right”) to require us to repurchase some or all of their shares of perpetual strife preferred stock at a cash repurchase price equal to the stated amount of the perpetual strife preferred stock to be repurchased, plus accumulated and unpaid regular dividends, if any, to, but excluding the fundamental change repurchase date. Our business and an investment in the perpetual strife preferred stock involve significant risks. These risks are described under the caption “ Risk Factors” beginning on page S-16of this prospectus supplement and in the documents incorporated by reference into this prospectus supplement. Neither the Securities and Exchange Commission nor any state or foreign securities commission or regulatory authority has approved or disapproved of the perpetual strife preferred stock or passed upon the adequacy or accuracy of this prospectus supplement or the accompanying prospectus. Any representation to the contrary is a criminal offense. We expect to deliver the perpetual strife preferred stock in book-entry form only through the facilities of The Depository Trust Company on or about the next trading day following the date of purchase.

| TD Cowen |     | Barclays |     | The Benchmark Company |

Prospectus supplement dated May 22, 2025.

TABLE OF CONTENTS PROSPECTUS SUPPLEMENT

| ABOUT THIS PROSPECTUS SUPPLEMENT                                      |     | S-1  |
| FORWARD-LOOKING STATEMENTS                                            |     | S-3  |
| PROSPECTUS SUPPLEMENT SUMMARY                                         |     | S-7  |
| THE OFFERING                                                          |     | S-9  |
| RISK FACTORS                                                          |     | S-16 |
| USE OF PROCEEDS                                                       |     |