MicroStrategy’s $1.38B Note Buyback Heightens Eight-Month Cash Runway Risk
MSTR•As of May 25, MicroStrategy holds 843,738 Bitcoin, faces $6.7 billion in convertible notes and $15.5 billion in preferred stock with $871 million cash against $1.5 billion in annual dividend obligations, yielding under eight months of runway if Bitcoin remains flat. The company used $1.38 billion to repurchase zero-coupon 2029 notes, heightening liquidity risk.
1. Balance Sheet Assessment
As of May 25, MicroStrategy holds 843,738 Bitcoin, carries $6.7 billion of aggregate convertible notes and $15.5 billion of preferred stock notional, and retains $871 million in USD reserves. The annual dividend obligation on its preferred stack is approximately $1.5 billion, suggesting less than eight months of cash runway if no new capital is raised and Bitcoin prices stay flat.
2. Convertible Note Buyback
MicroStrategy repurchased $1.5 billion principal amount of its zero-coupon Convertible Senior Notes due 2029 for approximately $1.38 billion in cash, realizing an 8% discount to par. While retiring non-interest-bearing debt can be accretive, the decision has drawn criticism for using scarce cash reserves rather than preserving liquidity for preferred dividends.
3. Potential Liquidity Scenarios
With a shrinking cash buffer, the company may face a choice between liquidating Bitcoin holdings or cutting preferred dividends if Bitcoin fails to rally or fresh capital is not secured. An external analyst warns that Bitcoin holders, common shareholders and preferred investors could all face losses within the next four months unless conditions improve.




