ANALYSIS • BEARISH • 2026-02-08

MicroStrategy Under Pressure as Bitcoin Falls: An In-Depth Analysis

This article examines the financial pressures facing MicroStrategy (MSTR) as Bitcoin's value declines, focusing on its preferred shares, liquidity, and the reflexive relationship with Bitcoin prices.
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MicroStrategy Under Pressure as Bitcoin Falls: An In-Depth Analysis

Since the start of 2026, Bitcoin's value has dropped nearly a quarter, placing significant pressure on MicroStrategy (MSTR), which holds a substantial amount of Bitcoin on its balance sheet. This article delves into the mechanics of MicroStrategy's financial situation, including preferred shares, liquidity runway, convertible debt, and the inherent risks associated with Bitcoin's price fluctuations.

Bitcoin Holdings and Financial Position

MicroStrategy currently holds 713,502 Bitcoins, financed partly through debt. In 2025, the company raised approximately $25.3 billion through its Bitcoin treasury. However, the market value of these Bitcoins has fluctuated around $48 billion, indicating a significant discount to intrinsic value as Bitcoin prices decline. This situation raises questions about the sustainability of MicroStrategy's financial strategy, often described as financial alchemy by its CEO, Michael Saylor.

Dividend Pressure from Preferred Shares

To finance its operations, MicroStrategy has issued new shares, including preferred shares that pay a monthly dividend. In 2025, the company raised about $5.5 billion through these preferred shares, which currently have an implied dividend rate of 9.6%. However, as the price of these preferred shares falls below the issue price of $100, the dividend rate increases, currently standing at approximately 11.25%. This situation creates a challenging environment for MicroStrategy, as it must maintain liquidity to meet these dividend obligations.

Liquidity Runway and Reserve Pot

MicroStrategy has reported a liquidity reserve of $2.25 billion, which is expected to cover approximately 2.5 years of dividend payments, according to Saylor. However, this reserve is contingent on Bitcoin's price stability. If Bitcoin were to drop significantly, for instance, to $40,000, MicroStrategy could face immense pressure to liquidate some of its Bitcoin holdings to meet financial obligations. Saylor has publicly expressed a desire to avoid such a scenario, advocating for a 'HODL' strategy—holding onto Bitcoin for dear life.

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Convertible Debt and Refinancing Risks

In the past, MicroStrategy has also raised over $8 billion through convertible bonds, which allow bondholders to convert their debt into equity if the stock price exceeds a certain threshold. Currently, these bonds are trading below the conversion price, posing a risk to bondholders. As noted by Tom Simonts, a senior economist at KBC, the immediate risk lies not with MicroStrategy but with the bondholders. If the bonds remain 'underwater,' MicroStrategy may need to repay them in cash within a few years or restructure the debt, further complicating its financial landscape.

The Reflexivity of Bitcoin Prices

The relationship between MicroStrategy's financial health and Bitcoin's price is highly reflexive. A significant decline in Bitcoin prices not only affects the market value of MicroStrategy's holdings but also puts pressure on its liquidity and ability to meet dividend obligations. As Bitcoin's value decreases, the risk of having to sell off assets increases, which could lead to a downward spiral in both Bitcoin and MicroStrategy's stock price.

Conclusion

Given the current market dynamics and the pressures outlined, MicroStrategy appears to be in a bearish position. The company's reliance on Bitcoin for its financial strategy, combined with the increasing dividend obligations and potential liquidity issues, suggests that it may struggle to maintain its current trajectory. The risks are twofold: a further decline in Bitcoin could exacerbate financial pressures, while a recovery could provide some relief. However, the uncertainty surrounding Bitcoin's price makes it challenging to predict a stable future for MicroStrategy.

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