Michael Saylor's Strategy resumes Bitcoin buying

Michael Saylor stopped buying Bitcoin for 10 weeks. That's the longest pause since he turned his software company into a Bitcoin-buying machine years ago. On Aug. 30, he posted "We're ₿ack." The company, now called Strategy, bought 4,603 coins for about $370 million, lifting its total holdings past 845,000 Bitcoin.

The timing says a lot. Strategy's stock has been under pressure. Its "buy Bitcoin with borrowed money" model has drawn more skepticism than it used to. Bitcoin itself just flashed a "death cross." That's a technical signal where a short-term price average drops below a long-term one. Traders often read it as bearish. Yet Strategy came back buying anyway, funding part of the purchase through share sales rather than new debt. Saylor is betting the pause was temporary, not a retreat.

Keep reading — what to watch

Is this the bottom, or a company doubling down at the wrong time? Strategy's buying has worked as a signal for years. When it buys, other treasury companies often follow. Bitcoin is closing out its best month since 2024, and Strategy's return lands right in the middle of that. The market will read it as a vote of confidence. Whether that vote turns out to be right is the thing to watch next.