Company: MSTR
Filing Date: 2025-07-07
Form Type: 424B5
Source: 0001193125-25-155880
Chunk: 68

Company: Strategy Inc
Filing Date: 2025-07-07
Form: 424B5
Chunk 68
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 adversely impact your
Offered Shares because of the inability to distinguish between your Offered Shares and the shares of STRD Stock subject to such adverse treatment. For example, adverse tax treatment of any shares of STRD Stock could negatively impact the trading
price of all shares of STRD 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 STRD 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 STRD 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 STRD Stock (including the Offered Shares).

Extraordinary Dividends

If any shares of STRD Stock are treated as being issued at a price that exceeds their liquidation preference, such shares of STRD Stock would constitute
“disqualified preferred stock” for purposes of the extraordinary dividend rules. The liquidation preference of the STRD Stock is subject to adjustment in the manner described in this

S-47

prospectus supplement. 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 STRD Stock, your Offered Shares may be considered disqualified preferred stock unless you can clearly demonstrate that you purchased the Offered Shares in an offering other than one in which shares of STRD Stock are issued at such a price. If
the Offered Shares held by a corporate U.S. holder were considered disqualified preferred stock (including because such shares are indistinguishable from other shares of STRD Stock that are disqualified preferred stock) for any dividend received,
the holder generally will be required to reduce its tax basis (but not below zero) in the Offered Shares with respect to which the dividend is received by the non-taxed portion of the dividend. Please also
review the discussion above under “U.S. Holders—Distributions” for a discussion of extraordinary dividends.

Sales at a Discount

As discussed above under “U.S