Bitcoin Sold by Strategy for First Time Since 2022 Tax Loss

Strategy Sells Bitcoin for First Time Since Late 2022, Signaling Shift in Asset Use

MicroStrategy, the enterprise software company that has amassed a significant Bitcoin treasury, has sold a small portion of its holdings for the first time since late 2022. The transaction, which occurred between May 26 and May 31, involved the sale of 32 Bitcoin for approximately $2.5 million, at an average price of $77,135 per coin.

This marks a notable shift for the company, as it signals a willingness to utilize its Bitcoin reserves to service the preferred equity structure it has established. The proceeds from the sale are earmarked for funding distributions on preferred stock, according to a filing with the U.S. Securities and Exchange Commission.

A Departure from Tax Maneuvers

The recent sale is distinct from MicroStrategy’s previous disclosed Bitcoin transaction in December 2022. At that time, the company sold 704 Bitcoin for tax-loss harvesting purposes before repurchasing a larger amount just two days later. That earlier sale was widely interpreted as a tax-related maneuver rather than a strategic reduction in its Bitcoin exposure. The current sale, however, appears directly linked to its preferred stock obligations.

Bitcoin Holdings Remain Substantial

Despite this sale, MicroStrategy’s Bitcoin holdings remain substantial. As of May 31, the company held 843,706 Bitcoin, acquired at an aggregate purchase price of $63.87 billion, equating to an average purchase price of $75,699 per Bitcoin. The 32 Bitcoin sold represent a minimal reduction in its overall holdings but break a long-standing pattern where the company’s Bitcoin disclosures primarily focused on accumulation.

Capital Markets Activity Continues

During the same period as the Bitcoin sale, MicroStrategy also continued its capital markets activities. Between May 26 and May 31, the company sold 801,994 shares of its common stock (MSTR) through its at-the-market program, generating $128.3 million in net proceeds. As of May 31, MicroStrategy reported significant remaining issuance capacity for its stock and various series of preferred stock.

Executive Signals Openness to BTC Sales

The Bitcoin sale follows recent comments from Executive Chairman Michael Saylor and CEO Phong Le, who have indicated that MicroStrategy could sell Bitcoin under specific circumstances. Saylor, however, has consistently emphasized that the company anticipates acquiring more Bitcoin than it sells, keeping the market attentive to whether any individual sale is offset by larger purchases.

The question of whether the company bought more Bitcoin than it sold during this latest reporting period remains open. On May 31, Saylor posted “Working ₿etter” on X, a phrase often preceding formal company announcements about Bitcoin purchases. However, no corresponding buy announcement had been made public as of press time.

Dollar Reserve and Dividend Declarations

MicroStrategy also disclosed that its U.S. dollar reserve stood at $900 million as of May 31. This reserve, established in December 2025, is a designated liquidity pool intended to support preferred stock dividends and debt interest payments. This reserve is central to the company’s newer capital structure, which integrates preferred equity, common stock issuance, and Bitcoin holdings into a balance-sheet model reliant on sustained liquidity.

The company’s board declared cash dividends payable on June 30 to shareholders of record as of June 15. These include payments for various preferred stock series, such as $2.50 per share for STRF, $0.958333333 per share for STRC, €2.50 per share for STRE, $2.00 per share for STRK, and $2.50 per share for STRD. The regular dividend rate on its Series A Perpetual Stretch Preferred Stock (STRC) will remain at 11.50% per annum for monthly periods beginning on or after June 1.

At press time, Bitcoin was trading at $71,637.

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