Strategy signals renewed Bitcoin buying plan

Strategy’s Saylor hints at new Bitcoin buy as key dividend vote nears

Strategy signals possible new Bitcoin accumulation

Strategy may be preparing to resume large-scale Bitcoin purchases after chair Michael Saylor posted a new acquisition chart on social media on Sunday, a move that has often preceded formal buy announcements.

The post landed as Bitcoin traded near $73,566, down about 3.65% in May, and just days before a proxy vote on a change to the company’s dividend policy. Market participants read the message as a signal Strategy could soon add to its already sizable holdings.

Company disclosures show Strategy currently holds 843,738 Bitcoin at an average purchase price of $75,701 per coin.

Social media pattern raises expectations

Saylor’s latest post featured a chart summarizing nearly six years of Bitcoin accumulation. Similar charts in the past have typically been followed by filings revealing fresh purchases, prompting traders to watch closely for a repeat.

The apparent restart of the buying program would follow a recent pause, during which Strategy repurchased $1.5 billion of its convertible notes for $1.38 billion in cash, a move aimed at strengthening its balance sheet.

At the same time, chief executive officer Phong Le has recently signaled more flexibility around selling Bitcoin if it would benefit shareholder value, a notable shift from the long-standing “never sell” message that has shaped the firm’s image in digital asset markets.

Technical backdrop: 200-week moving average climbs

On the macro side, Blockstream CEO Adam Back highlighted that Bitcoin’s 200-week moving average has moved above $61,000. Many traders view this long-term trendline as a key gauge of underlying momentum and a potential floor during major market cycles.

The prospect of renewed buying from Strategy is arriving as the market digests conflicting flows. BlackRock’s IBIT fund has sold roughly $2.1 billion in Bitcoin over the past ten days, underscoring divergent positioning among major players.

If Strategy repeats the size of prior acquisitions, any confirmed purchase could remove a significant amount of supply from the market, intensifying focus on upcoming company disclosures.

Dividend policy change heads to June vote

Alongside the Bitcoin signals, Strategy is preparing for a shareholder vote on a proposal to change the payment schedule for dividends on its STRC perpetual preferred stock.

The amendment would shift distributions from monthly to semi-monthly, a change the firm says is intended to improve liquidity and price stability for the securities it uses to raise capital for its Bitcoin-focused treasury strategy.

Company communications list the vote date as June 7 in one notice and June 8 in another, with proxy materials tying the motion to the firm’s broader efforts to fine-tune its capital structure.

Terms of the proposal and turnout challenge

According to Strategy’s filings, the dividend measure needs support from at least 50% of the 85 million shares outstanding as of April 17, 2026.

Le released a short video last week outlining the proposal and urging shareholder participation. An internal notice also reminded employees that proxy links and supporting documents are available via the company portal.

The company’s push reflects a wider turnout gap in corporate governance. Data from a Harvard Law School forum report shows that retail shareholders have voted only about 29% of their eligible shares over the past five proxy seasons, while institutional holders have participated on roughly 77% of their positions.

What traders are watching next

The outcome of the June vote will help determine how flexibly Strategy can manage its capital structure, which in turn may influence how it funds future operations and acquisitions, including potential Bitcoin buys.

In the near term, traders are watching three key elements:

• any regulatory filing confirming new Bitcoin purchases by Strategy
• the result of the dividend policy vote and its impact on the firm’s funding tools
• the behavior of long-term technical indicators such as the 200-week moving average, which many see as a barometer of Bitcoin’s structural trend

Together, these signals will shape market expectations for both Strategy’s next move and Bitcoin’s broader price path.