Michael Saylor, founder and executive chairman of Strategy, posted “Working ₿etter” on X on May 31, drawing immediate speculation from traders and market watchers about another Bitcoin (BTC) acquisition.
The message echoes a familiar pattern that market watchers have learned to follow. Strategy has historically disclosed new Bitcoin purchases within days of similar posts, turning each update from Saylor’s account into a closely followed signal for a potential 8-K filing.
Longest Purchase Pause in Recent Months
Strategy has not added to its holdings since May 18, the longest gap in its recent weekly buying run. The company holds 843,738 Bitcoin as of May 31, per StrategyTracker data.
The reserve value stands at approximately $62.24 billion, with an average acquisition cost of $75,701 per coin.
The post also follows Strategy’s brief Coinbase Prime move last week. The company deposited 411 BTC there, which pushed Polymarket odds of a 2026 Bitcoin sale above 90%, then withdrew the funds hours later in a reversal that cooled the sell-off narrative.
Bitcoin Balance Sheet Scrutiny Grows
A new purchase would come amid rising concern over MicroStrategy’s capital position. The company spent $1.38 billion in May buying back $1.5 billion face value of its 2029 convertible notes, trimming its USD reserve to approximately $871 million from around $2 billion before the transaction.
Arca chief investment officer Jeff Dorman published a direct warning about the capital flywheel, arguing that roughly $15 billion in outstanding preferred stock and approximately $1.5 billion in annual dividend obligations now put real strain on the accumulation model.
“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,” Dorman stated.
Saylor acknowledged at Q1 2026 earnings that Bitcoin sales remain an option if other capital sources run short. Gold advocate Peter Schiff has repeatedly cited that comment in his ongoing liquidity critique of the firm.
A June 8 vote by STRC holders on shifting preferred dividends to semi-monthly payments adds another near-term capital deadline to the mix.
The post may precede a formal acquisition filing or simply be routine communication. Either way, the next few days will indicate where Strategy’s treasury playbook is headed.