Bitcoin Updates Today: MicroStrategy's Momentum Falters: Bitcoin Purchases Fail to Boost Falling Shares

MicroStrategy's (MSTR) bold

acquisition approach and reliance on leveraged financing have left the company vulnerable, as its shares are pressured by market swings and uncertainty about index inclusion. The firm, which has positioned itself as a leading corporate advocate for Bitcoin, during a market downturn, increasing its total Bitcoin holdings to 649,870 BTC, now worth roughly $48.37 billion. Nevertheless, its share price has , sitting at $186 as of November 17, 2025, amid worries about dilution from equity and convertible bond issuances.

The company's market-implied net asset value (mNAV)—which compares enterprise value to the market value of its Bitcoin—has

, a sharp decline from its historical average of 2.1x. This narrowing has diminished the "flywheel" dynamic that previously enabled MicroStrategy to issue shares at a premium to its Bitcoin per-share value, then use the proceeds to buy more BTC. Recent policy adjustments allowing share issuance at lower mNAV levels have about additional dilution.

Adding to these difficulties, MicroStrategy's core business intelligence software segment is also under pressure. In the first quarter of 2025, revenue declined 3.6% year-over-year to $111.1 million, and adjusted operating income turned negative at -$3.6 million. Although subscription revenue increased by 62% and now makes up 33% of total revenue, the move from traditional licensing to cloud-based offerings has . The company’s $8.1 billion in debt, accumulated to finance Bitcoin acquisitions, increases its exposure if cryptocurrency prices stagnate or fall.

Experts caution that being left out of the S&P 500 could further unsettle MicroStrategy’s stock. Despite CEO Michael Saylor’s efforts to secure a spot, the company’s volatile valuation and heavy Bitcoin exposure make it a risky candidate for major indexes.

that MicroStrategy may once again fail to join the S&P 500, pointing to its leveraged finances and recent share price weakness. Such an outcome could restrict institutional investment and worsen liquidity issues.

At the same time, MicroStrategy’s preferred securities strategy—which aims to cushion Bitcoin volatility while providing tax-advantaged income—has yet to gain significant traction with wealth managers and registered investment advisors. With the stock now trading below its long-term average mNAV, some analysts see a possible buying opportunity, though risks remain high

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As Bitcoin struggles to surpass its October peak of $126,270, MicroStrategy’s long-term commitment to the cryptocurrency is facing a pivotal moment. While its latest purchases at an average price of $102,171 per BTC show strong belief in Bitcoin’s future, the company’s fate depends on its ability to weather market downturns and restore investor trust in its dual focus on innovative treasury management and software expansion.