On May 15, Strategy Inc. (Nasdaq: MSTR) announced on X that it had entered privately negotiated agreements to repurchase about $1.5 billion principal amount of its 0% Convertible Senior Notes due 2029. The company also filed a Form 8-K with the Securities and Exchange Commission (SEC), estimating the cash repurchase price at about $1.38 billion.

The final cash amount will partly reflect Strategy’s Class A common stock trading price during an agreed measurement period. Selected noteholders joined the transactions, which are expected to settle on or about May 19. After settlement, Strategy intends to cancel the repurchased notes, removing them from its outstanding debt base rather than leaving them available for resale or future conversion. The filing stated:

“The actual amount of cash paid in the repurchases could vary from the estimated aggregate repurchase price.”

Strategy issued the 2029 notes in November 2024, when it still operated as Microstrategy, to raise capital for bitcoin purchases and general corporate purposes. The offering reached $3 billion after purchasers exercised an additional allocation option. The repurchase follows a first quarter in which Strategy reported a $12.54 billion net loss, driven by $14.46 billion in unrealized losses tied to bitcoin holdings. As of writing, Strategy holds 818,869 BTC.

Strategy’s wider capital structure includes its $2 billion offering of 0% Convertible Senior Notes due 2030 in February 2025. It has also introduced Strategy Strike (Nasdaq: STRK), an 8% convertible preferred stock; Strategy Strife (Nasdaq: STRF), a 10% perpetual preferred security; Strategy Stride (Nasdaq: STRD), a junior perpetual preferred instrument; and Strategy Stretch (Nasdaq: STRC), a variable-rate perpetual preferred stock. Together, those instruments show how Strategy has layered convertible debt, preferred equity, and market-based issuance programs around its bitcoin treasury position.

That financing mix has brought Strategy’s bitcoin-sale language into sharper focus. During a first-quarter earnings call, Executive Chairman Michael Saylor said Strategy may sell some bitcoin to pay dividends. Chief Executive Phong Le stated that bitcoin sales could be considered if they were accretive to bitcoin per share. Those remarks differed from Saylor’s long-running public emphasis on retaining bitcoin, while still leaving any sale tied to specific capital needs and shareholder metrics. Strategy wrote:

“Strategy expects to fund the repurchases with available cash reserves, proceeds from sales of securities under its at-the-market offering program, and/or proceeds from the sale of bitcoin.”

The filing identifies bitcoin sales as one possible funding source, alongside cash reserves and securities-sale proceeds, without confirming any sale. Strategy also cited forward-looking risks tied to pricing, funding, settlement, cancellation, and remaining debt balances. That framing keeps the transaction linked to market conditions, equity pricing, and treasury flexibility rather than a single committed funding path.

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