Company: MSTR
Filing Date: 2025-03-10
Form Type: 424B5
Source: 0001193125-25-050408
Chunk: 113

Company: Strategy Inc
Filing Date: 2025-03-10
Form: 424B5
Chunk 113
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 rules that require the accrual of
such discount (or a greater discount that applies to any other shares of Perpetual Strike Preferred Stock) currently over the deemed term of the Perpetual Strike Preferred Stock as deemed distributions

S-76

under U.S. tax rules similar to those governing original issue discount for debt instruments. Due to fungible trading of the Perpetual Strike Preferred Stock, the IRS or a withholding agent may
treat any such discount as resulting in deemed distributions with respect to all shares of Perpetual Strike Preferred Stock, including those not issued at a discount (or issued at a lesser discount). Because any such deemed distributions received by
a holder would not give rise to any cash from which any applicable withholding could be satisfied, an applicable withholding agent may withhold such taxes from payments of cash or shares of common stock payable to the holder or require alternative
arrangements (e.g., deposit for taxes prior to delivery of conversion consideration).

Fast-PayStock Regulations

Under Treasury Regulations promulgated under Section 7701(l) of the Code (the “Fast-Pay
Stock Regulations”), if stock of a corporation is structured such that dividends paid with respect to the stock are economically (in whole or in part) a return of the stockholder’s investment (rather than a return on the stockholder’s
investment), then the stock is characterized as “fast-pay stock” and is subject to adverse tax reporting requirements and potentially penalties, as described below. In addition, under the Fast-Pay Stock Regulations, unless clearly demonstrated otherwise, stock is presumed to be fast-pay stock if it is structured to have a dividend that is reasonably expected to
decline (as opposed to a dividend rate that is reasonably expected to fluctuate or remain constant) (for such purpose, the dividend rate may be viewed as reasonably expected to decline if we are reasonably expected to stop paying regular dividends
on the Perpetual Strike Preferred Stock) or is issued for an amount that exceeds (by more than a de minimis amount, as determined under applicable Treasury Regulations) the amount at which the stockholder can be compelled to dispose of the stock. It
is not clear what amount would constitute “de minimis” in the case of stock with a perpetual term.

We do not intend to issue any shares of
Perpetual Strike Preferred Stock that would be treated as fast-pay stock, and we do not believe that we structured any Offered Shares, or will structure any Additional Shares, such that dividends paid by us
with