Business intelligence software leader Strategy announced that it has entered into privately negotiated agreements with certain holders of its outstanding 0% Convertible Senior Notes due 2029 to repurchase approximately $1.5 billion in aggregate principal amount of the notes.
The company stated the estimated aggregate cash repurchase price is approximately $1.38 billion. The final cash amount, however, will be subject to adjustment based in part on the daily volume-weighted average price (VWAP) of Strategy’s Class A common stock during an agreed measurement period.
In an official release by the Michael Saylor-founded company, Strategy confirmed that the actual cash paid could change depending on stock price fluctuations during the measurement window. The firm emphasized that the estimate reflects current conditions and that the ultimate figure will be finalized once the relevant market data are available.
Strategy said it plans to fund the repurchases with a combination of available cash on hand, proceeds from securities sales under its at-the-market offering program, and potentially proceeds from sales of Bitcoin (BTC). The company noted these sources will provide flexibility to complete the transactions while preserving liquidity for ongoing operations and strategic initiatives.
The transactions are expected to settle on or about May 19, subject to customary closing conditions. Strategy indicated that settlement timing could vary slightly if standard closing requirements or administrative matters require adjustment, but the company remains on track to complete the repurchases around that date.
Following the repurchases, Strategy also intends to cancel the repurchased notes. After cancellation, approximately $1.5 billion in aggregate principal amount of the 2029 convertible notes will remain outstanding. The cancellation is intended to reduce the company’s outstanding convertible debt, potentially lowering future interest and conversion-related dilution risks tied to those instruments.
This development follows the company’s recent financial reporting, which showed a significant first-quarter loss driven largely by declines in the market value of Bitcoin. In its quarterly results, Strategy reported a $12.5 billion loss for Q1, attributable primarily to changes in cryptocurrency valuations. Despite that loss, the company has continued to acquire Bitcoin as part of its treasury strategy, most recently purchasing another 535 BTC for $43 million.
As of the latest transactions, Strategy’s total Bitcoin holdings are reported at 818,869 BTC, acquired for an aggregate cost of nearly $62 billion. The company’s ongoing accumulation and occasional sales form part of a broader balance sheet and treasury-management approach that includes using digital assets as part of its capital strategy.
By repurchasing a substantial portion of its 2029 convertible notes, Strategy aims to manage its capital structure more actively and reduce the volume of convertible debt outstanding. The firm’s approach combines debt repurchases, selective securities offerings, and digital-asset transactions to balance liquidity needs, capital costs, and shareholder interests.
Strategy reiterated that the repurchase arrangements were privately negotiated with certain noteholders and are subject to standard closing conditions and adjustments. The company will provide final figures once the measurement period concludes and the repurchase price is fully determined in line with the agreed calculation methodology.
Investors and market observers will likely watch for the final cash amounts and any further commentary from Strategy about how the repurchases and potential Bitcoin sales fit into its broader financial and treasury plans. The transaction marks another step in the company’s ongoing efforts to optimize its capital base while managing exposure to asset-price volatility.