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Buyback at a Discount
Strategy announced it will repurchase approximately $1.5 billion of its 0% convertible notes due in 2029, retiring about half of the 2029 convertible note tranche’s total outstanding debt.
“agreeing to repurchase the debt for an estimated $1.38 billion”
In privately negotiated transactions with certain noteholders, Strategy agreed to repurchase the debt for an estimated $1.38 billion, according to the company’s Securities and Exchange Commission (SEC) filing.
The company said the transaction is set to settle on Tuesday of the week following the publication of the article, and that the final repurchase amount could "vary" from the estimated amount based on market conditions.
Strategy said it 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.
Strategy also said it plans to swap its convertible debt for equity over the next 3-6 years, gradually turning holders of its credit instruments into equity holders.
Bitcoin as Funding Lever
The buyback plan explicitly includes bitcoin as a potential funding source, with Cointelegraph quoting Strategy’s expectation to fund the repurchases with "and/or proceeds from the sale of bitcoin."
Michael Saylor’s prior comments in May 2026 were cited by TradingView as signaling Strategy could sell a portion of its Bitcoin holdings to fund dividend payments.
TradingView also reported that Strategy plans to equitize its debt in the coming years, while the company’s SEC filing described the repurchase as part of a broader shift toward turning convertible debt into equity.
Cryptonews.net added that the 2029 convertible notes were originally issued in November 2024 with a 0% coupon and $3 billion notional size, and that the debt matures on Dec. 2, 2029.
Cryptonews.net further stated the conversion price is $672.40 per share, while the current share price sits at $183.
Settlement, Cancellation, Dilution
Multiple outlets tied the deal’s timing to a May 19 settlement expectation, with TradingView saying the transaction is set to settle on Tuesday of the week following publication and Cryptonews.net stating settlement is expected around May 19.
“Following settlement, expected around May 19”
After settlement, Cryptonews.net said the repurchased notes will be cancelled, leaving roughly $1.5 billion of the 2029 notes outstanding.
The Block reported that Strategy entered into privately negotiated transactions with zero-coupon convertible note holders on May 14, with settlement expected on or about May 19, and that the company intends to cancel the repurchased notes following settlement.
TradingView said the repurchase is expected to retire about half of the 2029 convertible note tranche’s total outstanding debt, while AMBCrypto described the move as restructuring Strategy’s debt profile.
Across the coverage, the equity impact is framed around dilution risk as Strategy plans to equitize convertible debt over the next 3-6 years, a process that would "dilute existing stockholder value" by adding new equity shares.
