
Strategy owes about $1.5 billion annually in preferred-stock dividends but only generated $477 million in software revenue in 2025, creating a significant cash-flow shortfall. Grayscale's research head Zach Pandl highlights this as a financing problem rather than a Bitcoin price issue, since Bitcoin itself produces no yield and dividends must be paid in dollars regardless of BTC price. To cover payouts, Strategy sold 32 BTC in May, its first sale since 2022, but its preferred stock obligations have ballooned to $15.5 billion, raising concerns about sustainability. The core challenge remains that Bitcoin generates no cash flow, making it difficult to meet fixed dividend payments during price downturns or flat periods.