Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263746
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Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
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As Filed Pursuant to Rule 424(b)(5)
Registration No. 333-284510

PROSPECTUS SUPPLEMENT

(To Prospectus Supplement Dated November 4, 2025 and Prospectus Dated January 27, 2025)

SERIES A PERPETUAL STRIFE PREFERRED STOCK ANNEX

10.00% Series A Perpetual Strife Preferred Stock

We have entered into an Omnibus Sales Agreement (the “Sales Agreement”) with TD Securities (USA) LLC, Barclays Capital Inc., The Benchmark
Company, LLC, BTIG, LLC, Canaccord Genuity LLC, Cantor Fitzgerald & Co., Clear Street LLC, Compass Point Research & Trading, LLC, H.C. Wainwright & Co., LLC, Keefe, Bruyette & Woods, Inc., Maxim Group LLC, Mizuho Securities USA LLC,
Morgan Stanley & Co. LLC, Santander US Capital Markets LLC, SG Americas Securities, LLC, and TCBI Securities Inc. doing business as Texas Capital Securities (collectively, the “Agents”), dated November 4, 2025, relating to the sale
of shares of our class A common stock, par value $0.001 per share, and shares of several series of our preferred stock, par value $0.001 per share. In accordance with the terms of the Sales Agreement, under this prospectus supplement, relating to
the sale of our 10.00% Series A Perpetual Strife Preferred Stock (the “STRF Stock Annex”), we may offer and sell shares of our 10.00% Series A Perpetual Strife Preferred Stock (“STRF Stock”), having an aggregate offering
price of up to $1,659,967,526.88 from time to time through one or more of the Agents, acting as our sales agents. The shares of STRF Stock offered hereunder are among the securities described in the base prospectus supplement dated November 4, 2025
that we filed with the Securities and Exchange Commission on such date (the “base prospectus supplement”) and an accompanying prospectus dated January 27, 2025. This STRF Stock Annex should be read in conjunction with that base
prospectus supplement and accompanying prospectus and the contents of that base prospectus supplement and accompanying prospectus are incorporated by reference into this Common Stock Annex.

We had previously registered the offer, issuance and sale of up to $2,100,000,000 of our