Saylor post fuels bets MicroStrategy may buy more Bitcoin

Michael Saylor posted “Working ₿etter” on X on May 31, drawing trader speculation that MicroStrategy could add to its Bitcoin holdings. The company holds 843,738 BTC as of May 31 and last increased its position on May 18.

The post followed a familiar pattern: MicroStrategy has often disclosed new Bitcoin purchases in regulatory filings days after similar messages from Saylor. As of May 31 the company’s Bitcoin reserve was valued at about $62.24 billion, with an average acquisition cost near $75,701 per coin. The pause since May 18 is the longest gap in its recent run of weekly buys.

Last week MicroStrategy briefly transferred 411 BTC to Coinbase Prime and then reversed the transfer hours later. That sequence briefly increased speculation about a sale before the withdrawal reduced that narrative.

MicroStrategy completed a debt repurchase in May, spending $1.38 billion to retire about $1.5 billion in face value of 2029 convertible notes. The transaction reduced the company’s U.S. dollar reserve to roughly $871 million from about $2 billion before the repurchase. Holders of STRC preferred shares will vote on June 8 on a proposal to switch preferred dividends to a semi-monthly schedule.

Jeff Dorman, chief investment officer at Arca, warned about strains on MicroStrategy’s cash position, citing roughly $15 billion in outstanding preferred stock and about $1.5 billion in annual dividend obligations. He wrote: “MSTR, BTC and Pref holders are really in a bind. Someone is going to lose badly here, and it will happen in the next 4 months.”

Saylor acknowledged at MicroStrategy’s first-quarter 2026 earnings that selling Bitcoin remains an option if other capital sources prove insufficient. Any new Bitcoin purchase by the company would typically be disclosed in an 8-K filing within days of the transaction.

The coming days will show whether MicroStrategy files an acquisition notice following the May 31 post or maintains its recent pause in buys.