Company: MSTR
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001193125-25-263900
Chunk: 16

Company: Strategy Inc
Filing Date: 2025-11-04
Form: 424B5
Chunk 16
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 conversion of our 0% 
 Convertible Senior Notes due 2030, subject to adjustment in accordance with the terms of such notes;           |

| • |     | 2,593,931 shares of class A common stock potentially issuable as of October 31, 2025 upon conversion of our 
 0.875% Convertible Senior Notes due 2031, subject to adjustment in accordance with the terms of such notes; |

| • |     | 3,915,200 shares of class A common stock potentially issuable as of October 31, 2025 upon conversion of our 2.25% 
 Convertible Senior Notes due 2032, subject to adjustment in accordance with the terms of such notes; and          |

| • |     | 59,902,388 shares of class A common stock which are available for sale (assuming such shares are sold at                                                                      
 $264.67 per share, the last reported sale price of our class A common stock as reported on The Nasdaq Global Select Market on November 3, 2025), pursuant to Sales Agreement. |

SA-9

RISK FACTORS

An investment in the STRK Stock involves a high degree of risk. Before deciding whether to invest in the STRK Stock, you should carefully consider the risks described below, the risks described under the sections captioned “Risk Factors,” “Risk Factors Related to the ATM Offering Programs” and “Risk Factor Updates” contained in the accompanying base prospectus supplement and prospectus and in our most recent Annual Report on Form 10-K,any of our subsequent Quarterly Reports on Form 10-Q,and any of our Current Reports on Form 8-K,each of which are incorporated by reference herein in their entirety, together with other information in this STRK Stock Annex, in the accompanying base prospectus supplement and prospectus, and in any free writing prospectus that we have authorized for use in connection with this offering. If any of these risks actually occurs, our business, financial condition, results of operations or cash flow could be seriously harmed, resulting in a loss of all or part of your investment. As used in this section, (i) “we,” “us” and “our” refer to Strategy Inc and not to its subsidiaries; and (ii) “preferred stockholder” refers to a registered holder of the STRK Stock.

Risks Relating to the STRK Stock and This Offering

Although the STRK Stock is senior to our class A common stock, class