Strategy has already sold bitcoin before for tax loss harvesting in December 2022

Disclosure: The author of this story owns shares in Strategy (MSTR).

When executive chairman Michael Saylor confirmed on Strategy’s (MSTR) Q1 2026 earnings call on May 6 that the company was prepared to sell bitcoin, it appeared to mark a shift for the world’s largest publicly traded corporate holder of the cryptocurrency. But the move would not be unprecedented. In December 2022, Strategy sold bitcoin for tax-loss harvesting purposes — the same rationale the company now appears to be signaling to the market once again.

On Dec. 22, 2022, Strategy sold 704 bitcoin for approximately $11.8 million at $16,776 per coin, but immediately repurchased 810 bitcoin two days later.
The sale was designed to carry back capital losses against previous gains and generate a tax benefit. A tax loss harvesting event.

“MicroStrategy plans to carry back the capital losses resulting from this transaction against previous capital gains, to the extent such carrybacks are available under the federal income tax laws currently in effect, which may generate a tax benefit”.

Bitcoin fell 23% in Q1 2026, from $87,500 to $67,700. Under FASB fair value accounting rules adopted Jan 1, 2025, Strategy marks its entire bitcoin holdings to market every quarter, in Q1 posted a $12.54 billion loss which pushed unrealized losses directly through the income statement and generating a $2.2 billion deferred tax asset across its higher cost basis holdings.

According to the MSTR earnings call, assuming an $80,000 bitcoin price, Strategy has purchased over 434,000 BTC above $80,000 generating a $7.6 billion unrealized loss and a $2.2 billion deferred tax asset at a 29% tax rate.

If bitcoin recovers and Strategy sells appreciated bitcoins, that $2.2 billion tax can offsets future gains.

The primary goal for the company is to increase “bitcoin per share” which is the ratio of Strategy’s total bitcoin holdings divided by its total diluted shares outstanding.

The use of proceeds from the bitcoin sale is to retire the $8.2 billion in convertible debt, purchase MSTR common stock when the multiple to net asset value falls below 1.22x or fund $1.5 billion in annual dividend obligations from its perpetual preferred stock Stretch (STRC).

MSTR is up 1% in pre-market trading, while bitcoin trades above $81,000.