MicroStrategy Flags Possible Bitcoin Sales to Finance $1.5B Bond Buyback

MicroStrategy said Friday it plans to repurchase about $1.5 billion of its 0% Convertible Senior Notes due 2029 for roughly $1.38 billion in cash, retiring the debt below par. In a Form 8-K filing, the company said the buyback will be financed through cash on hand, proceeds from its at-the-market equity program and, notably, "potentially the sale of Bitcoin." The language marks a shift from CEO Michael Saylor's recent stance. Speaking at Bitcoin 2026, Saylor said any sale would be outweighed by additional purchases: "Even if we were to sell one Bitcoin, we'd be buying 10 to 20 more Bitcoin." MicroStrategy reported Bitcoin holdings of 818,869 BTC, acquired at an average cost of about $75,537 per coin. The 2029 notes were issued in November 2024 with $3 billion in notional value and a conversion price of $672.40 per MSTR share. With shares trading near $183, conversion appears unlikely, contributing to bondholders tendering at a discount. The company last disclosed adding 535 BTC on May 10. JPMorgan has estimated MicroStrategy's total Bitcoin purchases in 2026 could reach $30 billion. Saylor has described the buyback as part of a multi-year effort to "equitize" the company's roughly $8.2 billion debt stack. MicroStrategy said it has recorded 63,410 BTC in "Bitcoin Gain" so far in 2026, valued at about $5.1 billion at current prices. In premarket trading, MSTR shares fell about 2% as Bitcoin slipped to roughly $80,400. The explicit inclusion of potential Bitcoin sales introduces a new variable for investors. Selling BTC to retire discounted debt could strengthen the balance sheet without equity dilution, but it also raises the possibility of additional supply from one of Bitcoin's largest holders. Markets will be watching future filings and on-chain activity for signs the disclosure becomes action.