Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263900
Chunk: 100

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 100
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 lieu of a fractional share of
common stock will generally be treated as a payment in a taxable exchange for such fractional share, and gain or loss will be recognized on the receipt of cash in an amount equal to the difference between the amount of cash received and the amount
of adjusted tax basis allocable to the fractional share.

If our board of directors does not declare a distribution on the Offered Shares in respect of
any dividend period before the related dividend payment date, such deferred and unpaid dividend may be treated as dividends in arrears in the event of a conversion. Although it is not free from doubt, we intend to treat any such deferred dividend
(and any dividend that has been declared and not yet paid as well as any accrued but unpaid dividend in the then-current dividend period) as dividends in arrears for these purposes (all such dividends hereinafter referred to as “Dividends in
Arrears”). Common stock received upon conversion in respect of Dividends in Arrears on the Offered Shares will be treated as described above under “—Distributions.”

In the event a U.S. holder’s Offered Shares is converted pursuant to certain transactions (including our consolidation or merger into another person),
the tax treatment of such a conversion will depend upon the facts underlying the particular transaction triggering such a conversion. U.S. holders should consult their tax advisors to determine the specific tax treatment of a conversion under such
circumstances.

Because payments of common stock in respect of Dividends in Arrears will not give rise to any cash from which any applicable withholding
tax could be satisfied, if we (or an applicable withholding agent) pay backup withholding (as described below under “Information Reporting and Backup Withholding”) on behalf of a U.S. holder (because such U.S. holder failed to establish
an exemption from backup withholding), we (or an applicable withholding agent) may set off such payments against, or withhold such taxes from, shares of common

SA-63

stock payable to such holder or current or subsequent payments of cash, or require alternative arrangements (e.g., deposit for taxes prior to delivery of conversion consideration).

Exchange in Lieu of Conversion

If a U.S. holder
surrenders Offered Shares for conversion and such Offered Shares are exchanged with a designated financial institution, as described under “Description of STRK Stock—Conversion Rights—Exchange in Lieu of Conversion,” the U.S.
holder will be required to recognize gain or loss as described under “—Sale or