Company: MSTR
Filing Date: 2025-05-01
Form Type: 424B5
Source: 0001193125-25-109950
Chunk: 1

Company: Strategy Inc
Filing Date: 2025-05-01
Form: 424B5
Chunk 1
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 DESCRIPTION OF DEPOSITARY SHARES                     |     | 29 |
| DESCRIPTION OF WARRANTS                              |     | 32 |
| DESCRIPTION OF UNITS                                 |     | 33 |
| FORMS OF SECURITIES                                  |     | 34 |
| PLAN OF DISTRIBUTION                                 |     | 36 |
| LEGAL MATTERS                                        |     | 38 |
| EXPERTS                                              |     | 38 |

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ABOUT THIS PROSPECTUS SUPPLEMENT

This document is in two parts. The first part is the prospectus supplement, which describes the specific terms of this offering. The second
part is the accompanying prospectus, which provides more general information about securities we may offer from time to time, some of which does not apply to this offering. Generally, when we refer to this prospectus, we are referring to both parts
of this document combined. Before purchasing any of the class A common stock that we are offering, you should carefully read this prospectus supplement, the accompanying prospectus and all of the information contained in the documents incorporated
by reference herein and therein, as well as the additional information described under the heading “Where You Can Find Additional Information; Incorporation by Reference.” These documents contain important information that you should
consider when making your investment decision.

This prospectus supplement is part of a registration statement that we filed with the
Securities and Exchange Commission (the “SEC”) as a “well-known seasoned issuer” as defined in Rule 405 under the Securities Act, utilizing a “shelf” registration process. By using a shelf registration statement, we may
sell an unspecified amount of securities from time to time. Under this prospectus supplement, we may from time to time sell shares of our class A common stock having an aggregate offering price of up to $21,000,000,000, at prices and on terms to be
determined by market conditions at the time of the offering.

This prospectus supplement may add, update or change information contained
in the accompanying prospectus. To the extent there is a conflict between the information contained in this prospectus supplement, on the one hand, and the information contained in the accompanying prospectus or any document incorporated by
reference herein or therein and filed prior to the date of this prospectus supplement, on the other hand, you should rely on the information in this prospectus supplement; provided that, if any statement in one of these documents is inconsistent
with a statement in another document having a later date—for example, a document