Michael Saylor, founder and executive chairman of Strategy, posted "Working ₿etter" on X on May 31 — and the cryptocurrency market took notice immediately. The short message has traders watching for a new Bitcoin (BTC) acquisition announcement, following a pattern where similar posts from Saylor have preceded formal 8-K purchase disclosures within days.
The Longest Buying Pause in Recent Memory
Strategy has not added to its BTC holdings since May 18. That gap is the longest break in the company's recent run of near-weekly purchases. As of May 31, the firm holds 843,738 BTC, according to StrategyTracker data. The reserve is valued at roughly $62.24 billion, with an average acquisition cost of $75,701 per coin.
The timing of the post also follows a brief scare last week. Strategy deposited 411 BTC to Coinbase Prime, which briefly pushed Polymarket odds of a 2026 BTC sale above 90%. The company then withdrew the funds hours later, cooling the sell-off narrative before it gained real traction.
Capital Structure Under Pressure
Any new purchase would land against a backdrop of growing scrutiny over Strategy's finances. In May, the company spent $1.38 billion buying back $1.5 billion face value of its 2029 convertible notes. That move trimmed its USD reserve from roughly $2 billion down to approximately $871 million.
Arca chief investment officer Jeff Dorman published a pointed warning about the company's capital model, arguing that around $15 billion in outstanding preferred stock and approximately $1.5 billion in annual dividend obligations are putting real strain on Strategy's accumulation flywheel.
"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 himself acknowledged at Q1 2026 earnings that BTC sales remain an option if other capital sources fall short. Gold advocate Peter Schiff has repeatedly cited that comment as part of his ongoing liquidity critique of the firm.
Adding another near-term deadline to the picture: STRC holders are scheduled to vote on June 8 on whether to shift preferred dividends to semi-monthly payments.
What Comes Next
Saylor's post may precede a formal acquisition filing, or it may simply be routine communication. The pattern is well established enough that the market treats these posts as signals worth tracking, but nothing is confirmed until an 8-K hits. The next few days will clarify whether Strategy is extending its buying streak or holding its position while managing the capital pressures building around it.
_webp.webp&w=1920&q=75)
_webp.webp&w=1920&q=75)