Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263746
Chunk: 21

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 21
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 agent may treat any such discount as resulting in deemed taxable distributions with respect to all shares of STRF 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 STRF Stock offered or resold
from time to time, a holder of STRF 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 STRF 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 STRF Stock. See “Material United
States Federal Income Tax Considerations” for further discussion.

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

Certain provisions in the STRF 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 STRF Stock Annex, preferred stockholders will have the right to require us to repurchase their STRF Stock for cash. See “Description of STRF Stock—Fundamental
Change Permits Preferred Stockholders to Require Us to Repurchase STRF 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.

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

We have the right to redeem the STRF Stock in certain circumstances. See “Description of STRF Stock—Redemption
at Our Option.” If we redeem your STRF Stock, then you may be unable to reinvest any proceeds from the redemption in comparable investments at favorable dividend or interest rates.

Because the STRF Stock is held in book-entry form, holders of the STRF Stock must rely on DTC’s procedures to exercise their rights and remedies.

We initially issued the STRF Stock, and the STRF Stock sold in this offering will be initially issued, in the form of “global
certificates” registered in the name of Cede & Co., as nominee of DTC. Beneficial interests in global certificates are shown on, and transfers of global certificates are effected only through, the records maintained by DTC. Except in