Strategy Plans $1.5B Note Buyback While Leaving Door Open to Bitcoin Sales

Highlights:

• Strategy will retire about half of its 2029 convertible notes after settlement.
• The company expects a $1.38 billion cash bill, below face value.
• Bitcoin sales remain a possible funding source alongside cash and share proceeds.

Strategy Inc. has moved to cut part of its 2029 convertible debt through private deals with selected noteholders. The company said on Friday that it agreed to repurchase about $1.5 billion in principal amount. However, it expects to pay roughly $1.38 billion in cash, below the full face value. After the settlement, Strategy plans to cancel the repurchased notes and leave about $1.5 billion outstanding.

The transaction covers half of the 0% Convertible Senior Notes due 2029. The notes were issued in November 2024 through a $3 billion private placement. The debt carried no coupon, enabling the company to acquire Bitcoin cheaply. Moreover, the immediate common equity dilution was delayed as Bitcoin remained a central part of its treasury plan.

Strategy to repurchase $1.5 billion principal amount of 2029 convertible notes. $MSTR $STRC https://t.co/enRuc7PBkY

— Michael Saylor (@saylor) May 15, 2026

Strategy Moves to Trim Near-term Balance Sheet Pressure

The firm’s move aims to reduce future liabilities tied to its Bitcoin strategy. The company said the final cash payment could change during the agreed measurement period. This adjustment will partly follow the daily volume-weighted average price of its Class A stock. The notes mature on December 2, 2029, and carry a $672.40 conversion price.

By retiring the notes at a discount, Strategy reduces the size of a large maturity. Moreover, the move may improve flexibility across its capital structure. Investors have watched the company closely because its balance sheet depends heavily on Bitcoin prices. Therefore, debt management now sits beside accumulation as a core part of its public strategy.

The filing follows a difficult first quarter for the company. Strategy reported a $12.5 billion quarterly loss, driven largely by Bitcoin’s price decline. The company added 535 BTC earlier this week for about $43 million. Its total holdings now stand at 818,869 BTC, bought for nearly $62 billion.

Bitcoin Sales Remain Part of the Funding Mix

Strategy said it may fund the repurchase through cash reserves and securities sales. In addition, the company may use proceeds from Bitcoin sales if needed. This option marks a notable shift for a firm long known for nonstop accumulation. However, Saylor has already signaled that sales could support the balance sheet when useful.

During the May 5 earnings call, Michael Saylor described a model built around STRC preferred stock. The company can issue STRC, buy Bitcoin, and cover obligations through a mix of capital sources. He said the firm needs an annual Bitcoin appreciation of about 2.3% to break even. Above this rate, fresh capital could offset Bitcoin sales used for dividends or debt.

STRC recently posted a record daily trading volume of $1.53 billion on Thursday. Saylor highlighted the milestone on X and linked it to institutional interest. STRC pays an 11.5% annualized dividend and avoids common-equity dilution. In addition, its market value has grown near $8.5 billion in less than nine months.

All-time high volume. $1.53B of liquidity. Two cents of volatility. Closed at par. $STRC pic.twitter.com/aS0dSlkm7d

— Michael Saylor (@saylor) May 14, 2026

Meanwhile, MSTR stock has slipped to $174.82 in pre-market trading as Bitcoin pulled back below $80K. The decline came after the shares gained more than 5% in the previous session, after the crypto market structure bill advanced in Washington.