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Bitcoin is back—and so is Michael Saylor’s Strategy, which made its first buy in two months

August 31, 2026
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Bitcoin is back—and so is Michael Saylor’s Strategy, which made its first buy in two months

After a two-month dry spell, Strategy has resumed its Bitcoin buying spree. On Monday, the world’s largest digital asset treasury announced that it had purchased $370 million worth of Bitcoin at an average price of roughly $80,300 per BTC. Strategy shares rose nearly 3% following the announcement and were trading at about $130.

The company bought Bitcoin using part of the money it raised by selling newly issued MSTR shares, according to the SEC filing. It used the rest to pay dividends and repurchase STRC, a separate class of Strategy shares that pays investors regular income, and add $30 million to its cash balance.

Strategy’s latest purchase comes amid a brief rebound in Bitcoin, which was trading at roughly $78,800 on Monday. After spending much of the previous 10 months in a bear market, the cryptocurrency jumped more than 23% in a single day on Aug. 21, reclaiming $79,000 for the first time since May, according to crypto data aggregator CoinGecko. Bitcoin’s recent rally has also pushed the value of Strategy’s holdings back above what it paid for them, reversing a trend of steep paper losses.

Strategy, which holds 4% of the total Bitcoin supply, has struggled in recent months. The company’s aggressive accumulation model, which was historically funded through sales of new shares and borrowed money, came under pressure during the downturn. As Bitcoin’s value fell, Strategy’s holdings became less valuable, while its ability to raise fresh cash to continue its purchases weakened.

As a result, Strategy shifted from its earlier “never sell your Bitcoin” posture. In late June, when Bitcoin was trading at $58,500, a 53% drop from its all-time high, Strategy sold some of its holdings to meet its financial obligations. Over the summer, the company sold Bitcoin on three additional occasions. In total, the sales amounted to roughly $544 million.

This time around, Strategy has moved away from debt issuance as a Bitcoin-buying instrument. The company has faced growing shareholder pressure over its aggressive buying strategy, particularly as MSTR shares have fallen more than 60% over the past year. In response, Strategy has sought new ways to fund its approach—though several have drawn criticism or produced disappointing results.

In July 2025, Strategy introduced STRC, a dividend-paying share class designed to draw income-focused investors and give the company another source of cash for Bitcoin purchases. STRC investors receive regular payouts, unlike MSTR common shareholders, who mainly benefit if Strategy’s stock rises.

In June, after Bitcoin’s downturn strained the model, Strategy created a new financial backstop. The plan set aside cash for dividend and interest payments and gave the company the option to buy back shares or sell Bitcoin if needed. But Strategy still has to generate cash to make regular payments to STRC investors, leaving it reliant on new share sales or Bitcoin sales.

More recently, Strategy has focused on rebuilding its cash reserves to make sure it can keep paying dividends even if Bitcoin’s price remains weak.

The post Bitcoin is back—and so is Michael Saylor’s Strategy, which made its first buy in two months appeared first on Fortune.

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