Company: MSTR
Filing Date: 2025-05-22
Form Type: 424B5
Source: 0001193125-25-124554
Chunk: 21

Company: Strategy Inc
Filing Date: 2025-05-22
Form: 424B5
Chunk 21
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 of Perpetual Strife
Preferred Stock—Regular Dividends—Priority of Dividends; Limitation on Junior Payments; No Participation Rights— Limitation on Dividends on Parity Stock”).

A liquid trading market for the perpetual strife preferred stock may not be maintained.

Although we have listed the perpetual strife preferred stock on The Nasdaq Global Select Market, a liquid trading market for the perpetual strife preferred
stock may not continue to develop or be maintained, and the listing may be subsequently withdrawn. Accordingly, you may not be able to sell your perpetual strife preferred stock at the times you wish to or at favorable prices, if at all.

The liquidity of the trading market, if any, and future trading prices of the perpetual strife preferred stock will depend on many factors, including, among
other things, prevailing interest rates, our dividend yield, financial condition, results of operations, business, prospects and credit quality relative to our competitors, the market for similar securities and the overall securities market. Many of
these factors are beyond our control.

Market volatility could significantly harm the market for the perpetual strife preferred stock, regardless of our
financial condition, results of operations, business, prospects or credit quality.

The condition of the financial markets, prevailing interest rates and other factors could significantly affect the trading price of the perpetual strife preferred stock.

The condition of
the financial markets and changes in prevailing interest rates can have an adverse effect on the trading price of the perpetual strife preferred stock. For example, prevailing interest rates have fluctuated in the past and are likely to fluctuate in
the future, and we would expect an increase in prevailing interest rates to depress the trading price of the perpetual strife preferred stock. An increase in short- or long-term interest rates, including as a result of a rise in actual or expected
inflation, could cause the trading price of the perpetual strife preferred stock to fall significantly.

S-18

Future sales, or the perception of future sales, of our debt instruments, perpetual strife preferred stock, or other classes or series of liquidation parity or dividend parity preferred stock could depress the trading price of the perpetual strife preferred stock We may issue and sell additional notes, shares of perpetual strife preferred stock, or other classes or series of liquidation parity or dividend parity preferred stock in subsequent offerings to raise capital, or may issue such securities for other purposes, including in connection with the acquisition of additional bitcoin. For example, between January 1, 2024 and May 21, 2025, we issued and