This isn't the first time Microstrategy has been underwater in the 2022-2023 bear market. Strategy was under water on their Bitcoin buys by close to 50% at points. But in the last 1.5 years Microstrategy has purchased an insane amount of Bitcoin. Bumping their total holdings from around 125k Bitcoin in the beginning of 2022 to 713k Bitcoin as of today. (nearly 3% of the supply)
Bumping their average Bitcoin price from around $31k all the way up to $76k by buying an insane amount of Bitcoin over the last year, we might be broaching unprecedented grounds. Strategy issued a ton of preferred stocks with dividends to investors throughout 2025 and now will have to pay back investors eventually.
How much trouble are they in and how much can they afford to hold underwater Bitcoin before they have to sell?
Microstrategy Stock is currently near a two year low:
And the marketcap appears to be less than the value of their Bitcoin holdings.
Is there any chance they could be forced to sell causing cascading losses for all similar companies acting as Crypto Custodians?
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It should also be noted that Microstrategy outlined a few months ago (after the October 2025 Flash Crash) under what circumstances they would sell Bitcoin. Which was a change from "we will never sell Bitcoin" mantra that they had held for five+ years.
First, the company’s stock must trade below 1x mNAV, meaning the market capitalization falls below the value of its Bitcoin holdings.
Second, MicroStrategy must be unable to raise new capital through equity or debt issuance. This would mean capital markets are closed or too expensive to access.
Source
As far as I can tell the first part has already happened. Now the question is will the second part happen?
