Company: MSTR
Filing Date: 2025-03-10
Form Type: 424B5
Source: 0001193125-25-050408
Chunk: 20

Company: Strategy Inc
Filing Date: 2025-03-10
Form: 424B5
Chunk 20
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, Cantor Fitzgerald & Co., Maxim Group LLC, Mizuho Securities USA LLC and SG Americas Securities, LLC.               |

S-16

RISK FACTORS

An investment in the perpetual strike preferred stock involves a high degree of risk. Before deciding whether to invest in the perpetual strike preferred stock, you should carefully consider the risks described below, the risks described under the sections captioned “Risk Factors” contained 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, the other information contained in this prospectus, and the information and documents incorporated by reference in this prospectus, or 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 MicroStrategy Incorporated d/b/a Strategy and not to its subsidiaries; and (ii) “preferred stockholder” refers to a registered holder of the perpetual strike preferred stock.

Risks Relating to the Perpetual Strike Preferred Stock and This Offering

The perpetual strike preferred stock is junior to our existing and future indebtedness, structurally junior to the liabilities of our subsidiaries and subject to the rights and preferences of any other class or series of preferred stock then outstanding.

If we liquidate, dissolve
or wind up, whether voluntarily or involuntarily, then our assets will be available to distribute to our equity holders, including holders of the perpetual strike preferred stock, only if all of our then- outstanding indebtedness is first paid in
full. The remaining assets, if any, would then be allocated among the holders of our equity securities in accordance with their respective liquidation rights. If we issue any liquidation senior stock in the future, then the amounts due upon that
liquidation senior stock must be paid in full before any payments can be made on the perpetual strike preferred stock. If any assets remain after any liquidation senior stock is paid in full, those assets will be distributed pro rata among holders
of the perpetual strike preferred stock and any liquidation parity stock. There may be insufficient remaining assets available to pay the liquidation preference and unpaid accumulated dividends on the perpetual strike preferred stock. If