Edited By
Olivia Johnson

MicroStrategy is grappling with significant challenges as it finds itself underwater on its massive Bitcoin investment. Since 2022, the company has drastically increased its holdings from around 125,000 to an astonishing 713,000 Bitcoin, which now represents nearly 3% of the total supply.
With Bitcoin's average purchase price soaring from about $31,000 to $76,000, the financial strain is palpable. MicroStrategy's stock hovers near a two-year low, and its market capitalization appears less than the value of its Bitcoin stash. This poses the question: how long can the company hold onto its underwater investments?
Despite past periods of being underwater during the bear market of 2022-2023, the company's recent purchases raise red flags. Analysts worry about the implications if MicroStrategy must sell its holdings to address financial obligations. According to one observer, "Their Bitcoin holdings are THE majority, and theyβre underwater with it."
Interestingly, after a flash crash in October 2025, MicroStrategy adjusted its stance, stating they would sell Bitcoin under specific conditions. These include a market capitalization falling below one times the net asset value and a failure to raise new capital.
The sentiment among community members ranges from skepticism to outright concern. Key themes emerging from discussions include:
Liquidity Issues: Some believe that if MicroStrategy cannot service its debt from operating cash flows, it risks running into serious trouble.
Market Reaction: There are worries that a forced sale by MicroStrategy could lead to cascading losses for other players in the crypto space.
Confidence in Bitcoin: Still, many retain a bullish outlook on Bitcoin's long-term value, with one comment reflecting, "Bitcoin is here to stay and will be $10 million per coin someday."
"It seems like the actual strategy is to short MicroStrategy."
"They have enough cash on hand to service their debt for over 2.5 years without touching their Bitcoin treasury."
β³ MicroStrategy's holdings represent nearly 3% of total Bitcoin supply.
β½ The stock trades near a two-year low, concerning finance experts.
β» "When is Saylorβs next impromptu live stream?" - A user questions the strategy amidst the downturn.
As MicroStrategy contemplates its next moves, the market watches closely, wondering how long the company can sustain its Bitcoin position without facing dire consequences.
Thereβs a strong chance that MicroStrategy may face intensified pressure to liquidate a portion of its Bitcoin holdings if the stock price doesnβt stabilize or improve soon. Experts estimate around a 60% likelihood that the company will sell some of its assets to manage fiscal challenges, which could trigger a broader drop in cryptocurrency prices. If they succeed in raising additional capital without selling, they could regain footing, but market sentiment remains fickle. The stakes are high as every move is scrutinized by investors watching Bitcoin's volatility closely.
In the late 1990s, many tech companies acquired massive holdings in emerging internet infrastructure during a bubble. When the market crashed, those entities were left holding depreciated assets while struggling to maintain liquidity. Much like MicroStrategy today, the tech players then faced choices that dictated their survival. These decisions not only reshaped their futures but also impacted entire industries. Drawing from this, MicroStrategy's current predicament may echo a pivotal moment in the tech boom, showcasing how rapid investment can lead to significant consequences when market conditions shift unexpectedly.