Buy, Sell or Hold MSTR After Strategy’s First Bitcoin Sale in Years?

MicroStrategy, now operating under the name Strategy, sold 32 Bitcoin for $2.5 million last week to fund preferred stock dividends, marking its first sale since 2022. The company, led by CEO Phong Le, has historically followed a strategy of accumulating Bitcoin through equity issuance, holding over 843,000 Bitcoin with an average cost of $75,699 per coin. However, the stock has plummeted 67% over the past year and 31% in the last month, with Bitcoin currently trading at $64,282. The sale represents a tiny fraction (0.0004%) of its total holdings but signals financial strain, as preferred stock trades below par and further equity dilution would be costly. Strategy reported a Q4 2025 net loss driven by a $17.44 billion unrealized loss on digital assets, with full-year EPS of -$15.23. The stock has fallen 72% since July 2025, underperforming the S&P 500’s high single-digit gains. Analysts and investors debate whether the sale is a one-off or a shift in strategy. Polymarket assigns a 63% probability of MSCI index delisting by year-end 2026, which could trigger forced selling. Reddit sentiment remains bearish, with speculation about further Bitcoin sales if dividend coverage tightens. Management insists sales will only occur when advantageous, but the optics of selling under pressure have spooked investors. At a current price of $126, Strategy remains a Hold, balancing the Bitcoin treasury thesis with growing risks. A Bitcoin purchase announcement in early June could signal stability, while further sales or weak preferred stock demand would confirm a strategic shift. Investors are watching preferred prices and dividend timing ahead of the June 8 shareholder vote to gauge whether the treasury strategy remains intact.