Strategy Inc., the company formerly known as MicroStrategy, has a cash problem. JPMorgan analysts flagged concerns that the firm’s dollar reserves have thinned to the point where rebuilding them is no longer optional, it’s necessary to keep investors from heading for the exits.
The trigger: Strategy sold 32 BTC between May 26 and May 31. That’s a tiny amount relative to the company’s massive Bitcoin holdings, but the signal it sent was anything but small. When the largest corporate holder of Bitcoin starts selling, even in modest quantities, people notice.
The math behind the worry
Here’s the thing. Strategy carries roughly $1.7 billion in annual dividend obligations. Its current dollar reserves cover approximately 6.3 months of those payments. For a company that has built its entire identity around never selling Bitcoin, having less than seven months of dividend runway is, well, uncomfortable.
Back in December 2025, Strategy established a $1.44 billion USD reserve. The fund was built through equity offerings and designed to cover between 12 and 24 months of dividend payments. The whole point was to create a buffer large enough that the company would never need to liquidate Bitcoin to meet its obligations to preferred shareholders.
