Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263746
Chunk: 66

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 66
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 under this STRF Stock Annex, and may otherwise issue shares of STRF Stock (or resell any shares
of STRF 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 STRF 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 STRF 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 STRF Stock subject to such adverse treatment. For example, adverse tax treatment of any shares of STRF Stock could negatively impact the trading price of all shares of STRF 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 STRF 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 STRF 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 STRF Stock (including the Offered Shares).

Extraordinary Dividends

If any shares of STRF Stock are treated as being issued at a price that exceeds their liquidation preference, such shares of STRF Stock would constitute
“disqualified preferred stock” for purposes of the extraordinary dividend

SA-40

rules. The liquidation preference of the STRF Stock is subject to adjustment in the manner described in this STRF Stock Annex. It is not entirely clear how such an adjustable liquidation
preference would be treated for purposes of applying the rules governing disqualified preferred stock and extraordinary dividends. However, it is possible that such adjustment may be taken into account for purposes of the disqualified preferred
stock determination. Even if your Offered Shares are not issued at such a price, due to fungible trading of the STRF Stock, your Offered Shares may be considered disqualified preferred stock unless you can