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

Company: Strategy Inc
Filing Date: 2025-05-22
Form: 424B5
Chunk 25
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 terms of the
stock or the related agreements or a significant change in the

S-20

relevant facts and circumstances. The relevant tax regulations do not indicate the types of significant changes in facts and circumstances that are intended to give rise to such a determination,
and therefore it is possible that such a change could arise when, for example, a compounded dividend rate becomes in effect.

We will issue shares of
perpetual strife preferred stock from time to time under this prospectus supplement (the “Offered Shares”) and may otherwise issue shares of perpetual strife preferred stock (or resell any shares that we or any of our subsidiaries have
purchased or otherwise acquired) from time to time (such issued or resold shares, the “Additional Shares”). We do not intend to issue any shares of perpetual strife preferred stock that would be treated as
fast-pay stock, and we do not believe that we structured any Offered Shares, or will structure any Additional Shares, such that dividends paid by us with respect to the perpetual strife preferred stock will be
economically a return of a stockholder’s investment. Moreover, we have obtained, and we intend to obtain in the future, advice of counsel in connection with offerings of perpetual strife preferred stock for the purpose of analyzing the
consequences of issuing such shares, including in light of any legal developments regarding the definition of fast-pay stock. As the liquidation preference of the perpetual strife preferred stock is subject to
adjustment in the manner described in this prospectus supplement, it is generally not expected that any Offered Shares or Additional Shares would be issued at such a level of premium above their liquidation preference at the time of sale of the
Offered Shares or Additional Shares so as to implicate the fast-pay stock rules. Nonetheless, there may be increased risk that the IRS could assert that such Offered Shares or Additional Shares constitute fast-pay stock.

Transactions involving fast-pay stock arrangements are treated
as “listed transactions” for U.S. federal income tax purposes. Issuers and holders of any shares of fast-pay stock would be required to report their participation in the transaction on IRS Form 8886
on an annual basis with their U.S. federal income tax returns and would also be required to mail a copy of that form to the IRS Office of Tax Shelter Analysis. Failure to comply with those disclosure requirements could result in the assessment by
the IRS of interest, additions to tax and onerous penalties. In addition, an accuracy-related penalty applies under the Code to any reportable