Michael Saylor, the Executive Chairman of Strategy, sparked renewed speculation of a major Bitcoin acquisition after posting a cryptic “Working Better” message on social media late Sunday morning, May 31. The post, which appeared on X, was accompanied by a bubble chart from the Iceland-registered site StrategyTracker.com, a specific visual signal that has consistently preceded past announcements of fresh Bitcoin buys by the corporation.
This potential move comes as Strategy balances two distinct corporate goals. The firm maintains a long-term target of holding 1,000,000 BTC, and with current holdings at 843,706 BTC, it remains approximately 156,294 tokens short of that milestone. Separately, Michael Saylor has stated his focus is on a seven-year timeline to maximize “Bitcoin per share” by 2033, regardless of short-term price fluctuations.
The market context for this latest hint is mixed. While technical investors noted that Bitcoin’s 200-week moving average recently climbed above $61,000, actual exchange data shows the asset trading at $73,566 at the time of the tweet. This price position remains below Strategy’s average purchase cost, yet the firm has historically purchased even when prices exceeded $100,000, showing a commitment to accumulation over market timing.
Strategy executes first Bitcoin sale in four years
Despite the bullish posturing from the chairman, Strategy recently confirmed its first disposal of Bitcoin since 2022. According to a Form 8-K filing with the U.S. Securities and Exchange Commission (SEC) dated June 1, 2026, the company sold 32 BTC between May 26 and May 31. The tokens were sold at an average price of $77,135 per coin, netting approximately $2.5 million.
This sale is a rare event for the firm, which last sold 704 BTC in December 2022 for tax-loss harvesting purposes. While the recent sale is small relative to the Bitcoin exchange supply, it signals a more active approach to capital allocation. Michael Saylor previously remarked in a May 2026 podcast with Natalie Brunell that it was “not unlikely” the firm would sell some holdings before year-end to optimize performance.
CEO Phong Le has echoed this sentiment, suggesting that “week-to-week” decisions to sell could be made if they prove accretive to shareholders. This internal shift occurs as Bitcoin price analysis reveals a market struggling with resistance, leaving roughly 40% to 50% of the holders in the Strategy ecosystem in a profitable position at current levels.
Aggressive accumulation vs shareholder value
The “Working Better” tweet appears designed to reinforce investor confidence amid these small-scale sell-offs and routine transfers. Rumors of a larger liquidation recently circulated after the firm moved 411.48 BTC to Coinbase Prime, though these were largely dismissed by the community. Proponents of the strategy, such as Adam Livingston, estimate the firm is adding roughly 1,822 BTC per trading day in 2026.
If this aggressive pace is maintained, Strategy would finish 2026 with 1.13 million BTC, surpassing its million-token target ahead of schedule. Such moves are viewed as critical for the firm’s long-term thesis, even as macro warning signs and rising yields occasionally dampen broader market sentiment. For Michael Saylor, the ultimate metric remains the company’s performance relative to its 2033 goals.
The firm appears to be navigating a more complex financial environment than in previous years, where simple accumulation was the primary focus. By balancing the million-coin target with tactical sales to maximize share value, the Virginia-based company is evolving its “Bitcoin standard” model. Whether the recent “Working Better” hint leads to an immediate purchase announcement is yet to be confirmed, but the historical pattern suggests the treasury is likely to expand soon.
