Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263719
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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 STRETCH PREFERRED STOCK ANNEX

Variable Rate Series A Perpetual Stretch 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 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 Variable Rate Stretch Preferred Stock (the “STRC Stock Annex”), we may offer and sell shares of our Variable Rate Series A Perpetual Stretch Preferred Stock (“STRC Stock”) having an aggregate offering price of up
to $4,200,000,000.00 from time to time through one or more of the Agents, acting as our sales agents. The shares of STRC 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 STRC 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 $4,200,000,000.00 of our STRC Stock under a prospectus supplement dated July 31