Company: MSTR
Filing Date: 2025-05-22
Form Type: 424B5
Source: 0001193125-25-124554
Chunk: 75

Company: Strategy Inc
Filing Date: 2025-05-22
Form: 424B5
Chunk 75
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 holder (because such non-U.S. holder failed to establish an exemption from dividend withholding), we (or an applicable withholding agent) may set off such payments against, or withhold such taxes from, current or subsequent payments of
cash or sales proceeds received by, or other funds or assets of, such holder, or require alternative arrangements in respect of such withholding taxes.

Multiple Issuances of Perpetual Strife Preferred Stock—Effect of Fungible Trading

We will issue Offered Shares from time to time under this prospectus supplement, and may otherwise issue shares of Perpetual Strife Preferred Stock (or resell
any shares of Perpetual Strife Preferred Stock that we or any of our subsidiaries have purchased or otherwise acquired) from time to time (such issued or resold shares, the “Additional Shares”). If your Offered Shares trade under the same
CUSIP or other identifying number as that of other shares of Perpetual Strife Preferred Stock, those other shares may not be distinguishable from your shares by persons such as subsequent purchasers and withholding agents. If we issue any 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 Offered Shares, such profile or treatment
could adversely impact your Offered Shares because of the inability to distinguish between your Offered Shares and the shares of Perpetual Strife Preferred Stock subject to such adverse treatment. For example, adverse tax treatment of any shares of
Perpetual Strife Preferred Stock could negatively impact the trading price of all shares of Perpetual Strife Preferred Stock in light of fungible trading of all such shares. In addition, the IRS could treat your Offered Shares as subject to the
adverse tax consequences applicable to other shares of Perpetual Strife Preferred Stock unless you are able to demonstrate that you acquired your Offered Shares in a specific offering and did not hold such other shares of the Perpetual Strife
Preferred Stock that are subject to adverse consequences. Prospective investors are urged to consult their tax advisors regarding these tax considerations.

Please also review the discussion below under “Fast-Pay Stock Regulations” for a discussion about the
potential application of those rules to the Perpetual Strife Preferred Stock (including the Offered Shares).

S-53

Extraordinary Dividends

If any shares of Perpetual Strife Preferred Stock are treated as being issued at a price that