Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263900
Chunk: 33

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 33
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 parties (such as withholding agents)
may not be able to distinguish the shares of STRK Stock offered or resold from time to time, a holder of STRK 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 STRK 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 STRK Stock. See “Material United States Federal Income Tax Considerations” for further discussion.

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

Certain provisions in the STRK 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 STRK Stock Annex, preferred stockholders will have the right to require us to repurchase their STRK Stock for cash. See “Description of STRK Stock—Fundamental Change Permits Preferred
Stockholders to Require Us to Repurchase STRK 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 or holders of our class A common stock may view as favorable.

Your investment in the STRK Stock may be harmed if we redeem the STRK Stock.

We have the right to redeem the STRK Stock in certain circumstances. See “Description of STRK
Stock—Redemption at Our Option.” If we redeem your STRK Stock, then you may not be entitled to benefit from potential future appreciation in the trading price of our class A common stock, and you may be unable to reinvest any proceeds
from the redemption in comparable investments at favorable dividend or interest rates.

You will not be compensated for the lost option value and lost dividends as a result of conversion upon a fundamental change.

If a “fundamental change” (as defined under the caption
“Description of STRK Stock—Definitions”) occurs, a preferred stockholder may convert its STRK Stock at any time before the close of business on the business day

SA-19

immediately before the related fundamental change repurchase date to receive a number of shares of our class A common stock based on the conversion rate then in effect, as described under the
caption “Description of STRK Stock—Conversion Rights