Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263746
Chunk: 20

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 20
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 shares of STRF Stock to adverse consequences” below.

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

An issuance of STRF Stock could have an adverse tax profile, which could subject holders of any other shares of STRF Stock to adverse consequences.

If we issue 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 shares of STRF Stock, since all such shares would trade under the same CUSIP or other identifying number,
your shares of STRF 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 STRF Stock subject to such adverse
treatment.

For example, notwithstanding our intent not to issue any shares of STRF Stock that are fast-pay stock,
the IRS could assert that certain shares of STRF Stock constitute fast-pay stock. See “—The tax rules applicable to “fast-pay stock” could result
in adverse consequences to holders of STRF Stock” above.

Furthermore, if any shares of STRF Stock are issued at a price that exceeds their
liquidation preference, such shares would constitute “disqualified preferred stock” within the meaning of Section 1059(f)(2) of the Code and any corporate U.S. holder generally will be required to reduce its tax basis (but not below
zero) in the STRF Stock by the amount of any dividends-received deduction it receives. The liquidation preference of the STRF Stock is subject to adjustment in the manner described in this STRF Stock Annex, which adjustment may be taken into account
for purposes of disqualified preferred stock determination. If any shares of STRF Stock issued are considered disqualified preferred stock, the other shares of STRF Stock could also be subject to same treatment as a practical matter due to fungible
trading.

SA-11

If any shares of STRF Stock are sold at a discount, such shares may be subject to rules that require the
accrual of such discount (or a greater discount than the discount that applies to any other shares of STRF Stock) currently over the deemed term of the shares as deemed distributions under U.S. tax rules similar to those governing original issue
discount for debt instruments. In that event, the IRS or a withholding