Company: MSTR
Filing Date: 2025-05-22
Form Type: 424B5
Source: 0001193125-25-124554
Chunk: 27

Company: Strategy Inc
Filing Date: 2025-05-22
Form: 424B5
Chunk 27
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 subject to such adverse treatment.

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

Furthermore, if any shares of perpetual
strife preferred 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 perpetual strife preferred stock by the amount of any dividends-received deduction it receives. The liquidation preference of the perpetual strife preferred stock is
subject to adjustment in the manner described in this prospectus supplement, which adjustment may be taken into account for purposes of disqualified preferred stock determination. If any shares of perpetual strife preferred stock issued are
considered disqualified preferred stock, the other shares of perpetual strife preferred stock could also be subject to same treatment as a practical matter due to fungible trading.

If any shares of perpetual strife preferred 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 perpetual strife preferred 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 agent may treat any such discount as resulting in deemed taxable distributions with respect to all shares of perpetual strife preferred stock, including those not issued at a discount (or
issued at a lesser discount).

Because the IRS or other parties (such as withholding agents) may not be able to distinguish the shares of perpetual strife
preferred stock offered or resold from time to time, a holder of perpetual strife preferred stock might be subject to adverse tax consequences or might be required to demonstrate to the IRS (or such other parties) that the holder purchased the
perpetual strife preferred stock in a specific offering to which those adverse tax consequences did not apply. Moreover, any adverse tax consequences as described above in connection with the issuance of any Offered Shares or Additional Shares may
adversely affect the trading price of the perpetual strife preferred stock. See “Material United States Federal Income Tax