Woofun AI reports that Zach Pandl, head of research at Grayscale, has urged Strategy to liquidate at least $3 billion in Bitcoin to cover cash obligations for the next two years, a move he argues is essential to restore confidence in the firm's capital structure. Pandl contrasts this with a potential 50-basis-point increase in the dividend rate on Strategy's preferred stock, STRC, which would generate an additional $100 million in annual obligations over two years and further erode market trust.

Strategy currently faces an annual preferred dividend obligation of approximately $1.2 billion, primarily driven by STRC, its flagship "digital credit" preferred stock designed to trade near its $100 par value. The security has been sliding for weeks, hitting a low of $71.25 on Friday, representing a 28.75% discount to par, while Strategy's common stock MSTR closed at $82.31, marking a 26.86% decline for the trading week.

As the world's largest publicly-listed corporate Bitcoin holder, Strategy maintains a position of 847,363 BTC. A recent 8-K filing with the US Securities and Exchange Commission disclosed that the company acquired 520 Bitcoin for $34.9 million between June 15 and June 21, even as it increased its US dollar reserve by $300 million to $1.4 billion. This adjustment leaves the company with roughly 14 months of dividend coverage, a sharp contraction from a previous seven-year cushion.

Woofun AI data shows that blockchain analytics firm CryptoQuant recommends Strategy pause Bitcoin purchases to replenish its cash reserve, which has fallen 38% in 2026. CryptoQuant emphasizes that Strategy holds no obligation to sell Bitcoin to support STRC's price and could instead utilize methods like raising the current 11.5% dividend yield. Conversely, Bitcoin advocate Samson Mow contends that STRC possesses a built-in "self-repairing mechanism" where falling below the $100 reference price halts new ATM issuance, mechanically boosting yields for new buyers to attract demand and pull the price back toward par. This divergence in strategy highlights a critical tension between immediate liquidity preservation and long-term structural mechanics.