Following a two-month hiatus, Michael Saylor's Strategy, the world's largest corporate holder of Bitcoin, has reignited its buying spree. On Monday, the firm announced the acquisition of $370 million worth of Bitcoin at an average price of approximately $80,300 per coin. Following the news, Strategy shares climbed 4.4% to close at $132.94.

According to a filing with the U.S. Securities and Exchange Commission, the company used a portion of the proceeds from its recent issuance of additional MSTR shares to fund the purchase. The remaining capital was allocated to dividend payments, buybacks of STRC shares—a fixed-income class of stock—and an additional $30 million boost to its corporate cash reserves. This latest acquisition came during a brief Bitcoin rebound, with the cryptocurrency trading around $78,800 on Monday.

Data from CoinGecko shows that after a bearish stretch for most of the past ten months, Bitcoin surged over 23% on August 21, climbing back above the $79,000 mark for the first time since May. The recent price recovery has also pushed the market value of Strategy's Bitcoin holdings back above its aggregate cost basis, reversing a period of substantial unrealized losses on paper.

Controlling roughly 4% of the total Bitcoin supply, Strategy has faced a challenging few months. The company's aggressive accumulation model, traditionally funded through stock issuance and debt, came under significant strain during the market downturn. As Bitcoin's price fell, the value of the company's holdings shrank, and its ability to raise fresh capital for further purchases diminished.

This pressure forced a shift from Strategy's long-held "never sell Bitcoin" stance. In late June, when Bitcoin dropped to $58,500—53% below its all-time high—the company sold a portion of its holdings to meet financial obligations. Over the summer, it executed three more sales, totaling approximately $544 million.

Notably, this time around, Strategy has not relied on debt issuance to fund its Bitcoin purchases. The aggressive strategy has faced mounting shareholder pressure, especially with MSTR shares down more than 60% over the past year. In response, the company has sought alternative funding sources, though some of these initiatives have drawn criticism or underperformed expectations.

In July 2025, Strategy introduced STRC shares, a dividend-paying class designed to attract income-focused investors while creating another funding stream for Bitcoin acquisitions. STRC holders receive regular distributions, whereas MSTR common shareholders benefit primarily from share price appreciation.

When market conditions deteriorated in June, Strategy built a new financial safeguard mechanism. This plan set aside cash for dividend and interest payments and gave the company the option to repurchase shares or sell Bitcoin if necessary. However, the ongoing need to generate cash for STRC distributions means Strategy remains dependent on either issuing more stock or selling its Bitcoin holdings. Recently, the company has focused on rebuilding its cash buffer to ensure it can sustain dividend payments even if Bitcoin's price remains depressed.