Company: MSTR
Filing Date: 2025-03-10
Form Type: 424B5
Source: 0001193125-25-050408
Chunk: 106

Company: Strategy Inc
Filing Date: 2025-03-10
Form: 424B5
Chunk 106
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 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

S-72

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 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 Perpetual Strike Preferred 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 Redemption of Offered Shares or
Common Stock.” In such case, the U.S. holder’s tax basis in the common stock received will equal the fair market value of the stock on the date of the exchange, and the U.S. holder’s holding period in the common stock received will
begin on the day after the date of the exchange.

Adjustment of Conversion Rate

The conversion rate of Perpetual Strike Preferred Stock is subject to adjustment under certain circumstances. Treasury Regulations promulgated under
Section 305 of the Code would treat a U.S. holder of Offered Shares as having received a deemed distribution includable in such U.S. holder’s income in the manner described under “—Distributions,” above, if and to the extent
that certain adjustments in the conversion rate (or failures to adjust the conversion rate) increase the proportionate interest of the U.S. holder in our assets or earnings and profits. For example, an increase in the conversion rate to reflect a
taxable dividend to holders of common stock will generally give rise to a deemed taxable dividend to the holders of Perpetual Strike Preferred Stock to the extent of any such holder’s allocable portion of our current or accumulated earnings and
profits. Thus, under certain circumstances, U.S. holders may recognize income in the