Michael Saylor’s Strategy has carried out its largest-ever Bitcoin sale, offloading 3,588 BTC worth approximately $216 million to fund preferred stock dividend payments while marking a notable departure from the company’s long-standing commitment to never sell its holdings.

According to a Monday filing with the US Securities and Exchange Commission, the company sold the Bitcoin at an average price of roughly $60,200 per coin, reducing its total holdings to 843,775 BTC. The sale comes just weeks after Strategy formally authorized a framework allowing Bitcoin sales to finance shareholder obligations.

Strategy pivots from Bitcoin-only accumulation

The latest transaction represents Strategy’s first significant Bitcoin sale since the company began accumulating the asset in 2020. Apart from a 704-BTC tax-loss harvesting transaction in 2022 that was quickly reversed and a sale of 32 BTC disclosed in June, Strategy had consistently maintained it would only buy and hold Bitcoin.

Saylor has spent years reinforcing that message publicly, repeatedly encouraging investors to "never sell your Bitcoin" while positioning Strategy as a perpetual Bitcoin accumulator.

The company's latest filing, however, signals a shift toward using its Bitcoin treasury as a financing tool. Strategy sold 1,363 BTC between June 29 and June 30 at an average price of $59,256, followed by another 2,225 BTC between July 2 and July 6 at an average price of $60,773.

The transactions follow Strategy's June 29 announcement that it would permit Bitcoin sales to fund dividend payments on its preferred stock while increasing the annual dividend rate on its STRC preferred shares to 12%.

Although Strategy maintained its $2.55 billion US dollar reserve after the sale, the move suggests the company is increasingly balancing its Bitcoin accumulation strategy with growing shareholder obligations.

STRC, one of Strategy's preferred stock offerings used to finance Bitcoin purchases, traded around $88.70 before Monday's market open, roughly 11% below its intended $100 par value. Trading below par makes it more difficult for Strategy to raise fresh capital through new share issuance and could require the company to offer higher dividend yields to attract investors.

The company's decision to monetize a portion of its Bitcoin holdings therefore reflects a broader capital management strategy rather than an abandonment of its long-term Bitcoin thesis.

Analysts remain bullish despite the sale

Before Strategy disclosed the transaction, research firm Bernstein said the company was unlikely to face forced Bitcoin liquidations because of its strong liquidity position.

Bernstein estimated Strategy has roughly 17 months of cash available to meet dividend and interest obligations, while its debt represents only about 13% of the value of its Bitcoin collateral. The company's next major principal repayment of approximately $1 billion is not due until the third quarter of 2028.

The research firm also described Strategy as an important stabilizing force in the Bitcoin market, noting that it continues to accumulate more Bitcoin overall even as many publicly traded mining companies have become net sellers while redirecting capital toward artificial intelligence infrastructure.

Despite the recent sale, Bernstein maintained its year-end Bitcoin price target of $150,000 and said it remains optimistic about Bitcoin's long-term outlook.

The disclosure nevertheless marks an important milestone for Strategy. After years of presenting itself as a company that would never sell Bitcoin under any circumstances, it has now demonstrated a willingness to tap its digital asset reserves to meet corporate financing needs—underscoring how shareholder obligations can reshape even the industry's most steadfast Bitcoin treasury strategy.