Saylor post revives bets MicroStrategy will buy Bitcoin

Michael Saylor posted “Working ₿etter” on X on May 31, prompting renewed speculation that MicroStrategy will restart Bitcoin purchases after halting buys on May 18. Traders and investors watch Saylor’s posts closely because similar updates have often preceded company disclosures of new acquisitions.

MicroStrategy held 843,738 Bitcoin as of May 31, with a reserve valued at about $62.24 billion and an average acquisition cost near $75,701 per coin. The gap from May 18 to May 31 was the longest pause in the company’s recent run of weekly purchases.

The May 31 post followed a brief transfer last week of 411 BTC to Coinbase Prime that was reversed hours later. The short-lived deposit had briefly raised expectations of a sale before the funds were withdrawn.

In May, MicroStrategy spent $1.38 billion to repurchase $1.5 billion face value of its 2029 convertible notes. That operation reduced U.S. dollar cash reserves to roughly $871 million from about $2 billion before the repurchase.

Jeff Dorman, chief investment officer at Arca, warned that roughly $15 billion in outstanding preferred stock and about $1.5 billion in annual dividend obligations could strain the company’s capital structure. He said, “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.”

Michael Saylor acknowledged at MicroStrategy’s first-quarter 2026 earnings that selling Bitcoin remains an option if other capital sources fall short. Commentator Peter Schiff has cited that acknowledgment in his critiques of the company’s liquidity.

Preferred stockholders will vote on June 8 on a proposal to change dividend payments to a semi-monthly schedule, adding a near-term decision that could affect cash flow. The May 31 post may precede a formal 8-K filing disclosing new purchases or be routine shareholder communication; market participants expect developments in the next few days that could clarify MicroStrategy’s plans.