MicroStrategy repurchases $1.5 billion of 2029 convertible notes at

MicroStrategy announced it will retire roughly $1.5 billion of its 0% convertible senior notes due 2029, paying about $1.38 billion in cash—a discount to par value [1]. The transaction, negotiated privately with select noteholders, represents half of the original $3 billion issuance from November 2024 and will leave about $1.5 billion of the notes outstanding after settlement around May 19 [3].

The company plans to fund the buyback with existing cash reserves, proceeds from its at‑the‑market equity offering, and potentially sales of bitcoin holdings, though a separate report says no bitcoin was sold for the deal [5]. By retiring debt at a discount, MicroStrategy reduces its liability by an estimated $120 million, easing the “cash repayment wall” that analysts feared could loom in mid‑2028 [2]. The conversion price of $672.40 per share remains far above the current stock price of roughly $183, leaving the notes deep out‑of‑the‑money and giving the firm leverage to negotiate favorable terms [1].

The move comes as both crypto and equity markets are weak—bitcoin slipped to $80,400 and MSTR shares fell 2% in pre‑market trading [1]. Despite the debt reduction, the stock price dropped 3% in pre‑market trading after the announcement, underscoring lingering investor concerns about the company’s heavy bitcoin exposure and the sizable remaining convertible debt [2]. The final repurchase price is tied to the volume‑weighted average price of MSTR’s Class A shares during a set measurement period, adding a variable pricing element to the transaction [3].

With roughly $1.5 billion of convertible notes still on the books, MicroStrategy’s balance sheet will continue to carry a significant liability that could pressure the stock if its price does not move closer to the $672.40 conversion strike. How the firm finances any future debt reductions—whether through further bitcoin sales or equity issuances—will be a key factor for investors watching the interplay between its treasury strategy and market performance.