Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263759
Chunk: 17

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 17
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 Stock are not treated as being made out of our
current or accumulated earnings and profits. For the avoidance of doubt, our expectation on earnings and profits could change, therefore the U.S. federal income tax treatment of the distributions on STRD Stock could change. Holders of STRD Stock are
encouraged to consult with their tax advisors regarding the implications of our current or accumulated earnings and profits for U.S. federal income tax purposes.

The tax rules applicable to “fast-paystock” could result in adverse consequences to holders of STRD Stock.

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

SA-9

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 STRD 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.

The determination of whether stock is fast-pay stock is based on all the facts and circumstances. To determine if it
is fast-pay stock, stock is examined when issued, and, for stock that is not fast-pay stock when issued, when there is a significant modification in the terms of the
stock or the related agreements or a significant change in the relevant facts and circumstances. The relevant tax regulations do not indicate the types of significant changes in facts and circumstances that are intended to give rise to such a
determination.

We may issue shares of STRD Stock from time to time under this STRD Stock Annex (the “Offered Shares”) and may otherwise issue
shares of STRD Stock (or