Company: MSTR
Filing Date: 2025-05-22
Form Type: 424B5
Source: 0001193125-25-124554
Chunk: 26

Company: Strategy Inc
Filing Date: 2025-05-22
Form: 424B5
Chunk 26
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 transaction understatement attributable to a listed transaction if a significant purpose of the
transaction is the avoidance or evasion of U.S. federal income tax. Furthermore, certain material advisors would also be required to file a disclosure statement with the IRS. If we determine that we are required to file an IRS Form 8886 (including a
protective filing) in connection with the potential issuance of fast-pay stock with respect to any perpetual strife preferred stock, we intend to provide public notice to the applicable holders of the
perpetual strife preferred stock, which notice may be by a press release, by publication on our investor relations website, or by filing a current report on Form 8-K with the Securities and Exchange
Commission.

Notwithstanding our intent not to issue perpetual strife preferred stock that would be fast-pay
stock, the rules regarding the definition of fast-pay stock are unclear in certain respects and, therefore, the IRS could disagree with our determination and treat Offered Shares or Additional Shares as fast-pay stock. In addition, even if a particular issuance of Offered Shares or Additional Shares is not fast-pay stock, the treatment of any other shares of perpetual strife
preferred stock—including other Offered Shares or any Additional Shares—as fast-pay stock (for example, as a result of a determination by the IRS) could result in adverse consequences to holders of
all shares of perpetual strife preferred stock because the shares may be indistinguishable from each other. See “—An issuance of perpetual strife preferred stock could have an adverse tax profile, which could subject holders of any other
shares of perpetual strife preferred stock to adverse consequences” below.

Accordingly, holders of perpetual strife preferred stock are strongly
urged to consult their tax advisors regarding the Fast-Pay Stock Regulations and their potential consequences to an investment in the perpetual strife preferred stock.

An issuance of perpetual strife preferred stock could have an adverse tax profile, which could subject holders of any other shares of perpetual strife preferred stock to adverse consequences.

If we issue shares of perpetual strife preferred stock—whether Offered Shares or
Additional Shares—that have a different, and potentially adverse, tax profile or treatment for U.S. federal income tax purposes from your shares

S-21

of perpetual strife preferred stock, since all such shares would trade under the same CUSIP or other identifying number, your shares of perpetual strife preferred stock may be treated by
subsequent purchasers, withholding agents and potentially the IRS as having the same adverse tax profile or treatment if they are not otherwise distinguishable from the perpetual strife preferred stock