Michael Saylor Hints at Resuming Bitcoin Purchases This Week

Strategy's Michael Saylor has dropped another not-so-subtle hint about adding to the company's Bitcoin stash. The executive chairman took to X on Sunday, May 31, with a simple caption: "Working Better." Accompanying the post was the now-famous Orange Dots chart—a signal Saylor has repeatedly deployed whenever Strategy is ready to make a move.

The timing is noteworthy. Strategy had deviated from its aggressive buying cadence, opting instead to tackle some debt management. Last week, the firm repurchased the entire $1.5 billion principal amount of its 0% Convertible Senior Notes due in 2029, paying roughly $1.38 billion in cash—a tidy discount of about $120 million.

While handling that housekeeping, Strategy wasn't sitting idle. The company raised an additional $2 billion notional through its Variable Rate Series A Perpetual Stretch Preferred Stock and pulled in $84 million via MSTR Class A common share sales. All these proceeds went toward acquiring 24,869 BTC, valued at over $2 billion, according to regulatory filings.

As of May 25, Strategy's treasury sits at 843,738 BTC worth approximately $62.24 billion, with cash reserves hovering around $871 million. Not bad for a company that started as a business intelligence software firm.

"These transactions demonstrate the optionality we have built into Strategy's capital structure and our dynamic, multi-variate capital allocation model," Saylor noted. He added that the company maintains flexibility to fund strategic moves using "cash, Digital Equity, Digital Credit, or Digital Capital"—essentially, multiple ways to keep acquiring the orange coin.

On the on-chain front, blockchain trackers spotted some movement. On May 29, Lookonchain reported that Strategy transferred 411.48 BTC (roughly $30.3 million) to Coinbase Prime. Whether this signals a selloff or just some routine wallet reorganization remains to be seen—but Saylor's latest "Working Better" post suggests the buying might resume sooner rather than later.