Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263759
Chunk: 20

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 20
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 any dividends-received deduction it receives. The liquidation preference of the STRD Stock is subject to adjustment in the manner
described in this STRD Stock Annex, which adjustment may be taken into account for purposes of disqualified preferred stock determination. If any shares of STRD Stock issued are considered disqualified preferred stock, the other shares of STRD Stock
could also be subject to the same treatment as a practical matter due to fungible trading.

If any shares of STRD 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 STRD 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 STRD 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 STRD Stock offered or resold from time to time, a holder of STRD 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 STRD
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 STRD Stock. See “Material United States Federal Income Tax Considerations” for further discussion.

Provisions of the STRD Stock could delay or prevent an otherwise beneficial takeover of us.

Certain provisions in the STRD Stock could make a third-party attempt to
acquire us more difficult or expensive. For example, if a takeover constitutes a fundamental change, then, except as described in this STRD Stock Annex, preferred stockholders will have the right to require us to repurchase their STRD Stock for
cash. See “Description of STRD Stock —Fundamental Change Permits Preferred Stockholders to Require Us to Repurchase STRD Stock.” These fundamental change provisions could increase the cost of acquiring us or otherwise discourage a
third party from acquiring us or removing incumbent management, including in a transaction that preferred stockholders may view as favorable.

SA-11

Your investment in the STRD Stock may be