Strategy is moving to repurchase $1.5 billion worth of convertible notes while signaling that Bitcoin sales could be used to help fund the transaction.
Key Takeaways
- Strategy announced plans to repurchase around $1.5 billion of its 2029 convertible senior notes.
- The company may use cash reserves, share sales, and possible Bitcoin sales to fund the deal.
- The repurchase comes as Strategy continues expanding its massive Bitcoin treasury holdings.
- STRC preferred stock recently recorded a record $1.53 billion daily trading volume.
What Happened?
Strategy, the Bitcoin treasury company led by Michael Saylor and formerly known as MicroStrategy, revealed in a recent filing that it has entered into privately negotiated agreements with holders of its outstanding 0% Convertible Senior Notes due 2029.
The company plans to repurchase approximately $1.5 billion in aggregate principal amount of the notes for an estimated cash payment of around $1.38 billion. The final amount may still change depending on the volume weighted average price of Strategy’s Class A common stock during a designated measurement period.
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 Restructure Debt
The 2029 convertible notes were originally issued in November 2024 as part of a $3 billion offering carrying a 0% coupon rate. The debt matures on December 2, 2029, with a conversion price of $672.40 per share.
However, with Strategy shares currently trading far below that conversion price, the company appears to be taking advantage of market conditions to retire a portion of the debt at a discount.
Following completion of the transaction, Strategy said the repurchased notes will be canceled, leaving roughly $1.5 billion of the 2029 notes still outstanding.
The deal is expected to close around May 19, subject to customary closing conditions.
Bitcoin Sales Remain On The Table
One of the biggest talking points from the filing was Strategy’s acknowledgment that Bitcoin sales could potentially be used to help fund the repurchase.
The company stated that funding may come from a mix of existing cash reserves, proceeds from its at the market equity offering program, and possibly Bitcoin sales.
While Strategy has built its reputation around aggressively accumulating Bitcoin, the inclusion of possible Bitcoin sales signals the company is keeping financial flexibility open as it manages its balance sheet.
The announcement comes shortly after Strategy reported a massive $12.5 billion first quarter loss, largely tied to Bitcoin’s recent price decline.
Despite that loss, the company has continued purchasing more Bitcoin. Earlier this week, Strategy acquired another 535 BTC for approximately $43 million.
Strategy now holds 818,869 Bitcoin purchased for roughly $61.81 billion at an average acquisition price of $75,537 per coin.
STRC Trading Volume Hits Record High
The debt repurchase filing also arrived just one day after Strategy’s STRC preferred stock product posted record trading activity.
STRC, formally known as Strategy’s Variable Rate Series A Perpetual Stretch Preferred Stock, recorded an all time high daily trading volume of $1.53 billion. That surpassed the previous record of $1.1 billion set in April.
Michael Saylor highlighted the milestone on X, calling it an “all time high volume” event and framing it as a sign of growing institutional demand.
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
STRC currently offers investors an annualized dividend yield of 11.5% without diluting Strategy’s common equity. Since launching less than nine months ago, the instrument has reportedly grown to around $8.5 billion in market capitalization.
Reports also noted that Thursday’s trading activity could theoretically allow Strategy to raise more than $735 million through its at the market issuance structure, potentially enough to purchase over 9,000 additional Bitcoin at current market prices.
Strategy Continues Aggressive Bitcoin Expansion
Strategy’s latest move highlights the company’s ongoing effort to restructure its capital stack while continuing to expand its Bitcoin treasury strategy.
The company has previously stated plans to convert nearly $6 billion of convertible debt into equity over the next three to six years.
At the same time, Strategy continues deploying capital into Bitcoin at a rapid pace. The company has accumulated more than 101,000 BTC since March alone, including over 56,000 Bitcoin acquired after April.
CoinLaw’s Takeaway
In my experience, this move shows Strategy is becoming far more sophisticated in how it manages both debt and Bitcoin exposure. The company is no longer simply buying Bitcoin aggressively. It is now actively reshaping its balance sheet while using multiple financial instruments to support long term growth.
I found the mention of possible Bitcoin sales especially important because it shows Strategy is willing to stay flexible instead of treating Bitcoin holdings as untouchable assets. That could help reassure investors worried about liquidity and debt obligations during periods of market volatility.
