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Michael Saylor’s Strategy Repurchases $1.5 Billion of 2029 Convertible Notes

Strategy entered privately negotiated transactions to repurchase approximately $1.50 billion of its 0% Convertible Senior Notes due 2029, with settlement expected on May 19, 2026.

Sathish Kumar Kaliraj by Sathish Kumar Kaliraj
May 15, 2026
in Market Updates
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Michael Saylor’s Strategy Repurchases $1.5 Billion of 2029 Convertible Notes

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  • Strategy agreed to repurchase approximately $1.50 billion aggregate principal amount of its 0% Convertible Senior Notes due 2029.
  • The estimated aggregate cash repurchase price is approximately $1.38 billion.
  • The final repurchase price will depend partly on the volume-weighted average price of Strategy’s Class A common stock during the measurement period.
  • Strategy plans to fund the repurchases using cash reserves, ATM offering proceeds, and/or bitcoin sales.
  • The repurchased notes are expected to be cancelled after closing.

Strategy Announces Convertible Notes Repurchase

Strategy Inc entered into privately negotiated transactions with certain holders of its outstanding 0% Convertible Senior Notes due 2029 on May 14, 2026. Under the agreements, the company will repurchase approximately $1.50 billion aggregate principal amount of the notes.

The company estimated the aggregate cash repurchase price at approximately $1.38 billion. Strategy stated that the final repurchase amount remains subject to adjustment.

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

— Michael Saylor (@saylor) May 15, 2026

The details were disclosed in a Current Report on Form 8-K filed by the company. Michael Saylor also shared the announcement on X, while the information was additionally published through official government disclosure channels.

According to the filing, the final aggregate cash repurchase price will be based in part on the daily volume-weighted average price per share of Strategy’s Class A common stock during an agreed measurement period. The company said the total cash paid could vary depending on changes in the stock’s trading price during that period.

Funding Sources and Settlement Timeline

Strategy stated that it expects to fund the repurchases using available cash reserves, proceeds from sales of securities under its at-the-market offering program, and/or proceeds from the sale of bitcoin. The repurchases are expected to settle on or about May 19, 2026, subject to customary closing conditions.

Following completion of the transactions, Strategy said it intends to cancel the repurchased notes. After cancellation, approximately $1.50 billion aggregate principal amount of the 2029 Notes will remain outstanding. The filing stated that the report does not constitute an offer to sell or a solicitation of an offer to buy any security in any jurisdiction where such activity would be unlawful.

Recently, Strategy’s STRC preferred stock recorded $1.53 billion in daily liquidity, marking its highest trading volume since launch. Michael Saylor said the product reached an “all-time high volume” while maintaining “two cents of volatility.” The update follows Strategy’s previous week purchase of 535 Bitcoin for approximately $43 million, bringing its total holdings to 818,869 BTC valued at around $66.5 billion.

FAQs

1. What did Strategy announce regarding its 2029 Convertible Notes?
Strategy announced that it agreed to repurchase approximately $1.50 billion aggregate principal amount of its 0% Convertible Senior Notes due 2029 through privately negotiated transactions.

2. How much is Strategy expected to pay for the repurchase?
The estimated aggregate cash repurchase price is approximately $1.38 billion, although the final amount may change based on the agreed measurement period.

3. How will Strategy fund the repurchase transactions?
Strategy said it expects to fund the repurchases using available cash reserves, proceeds from its at-the-market offering program, and/or proceeds from bitcoin sales.

4. When are the repurchases expected to settle?
The repurchases are expected to settle on or about May 19, 2026, subject to customary closing conditions.

Source: Form 8-K

AI Disclosure: Cryip uses AI-assisted tools to help refine language — correcting spelling and grammar and simplifying complex terms for readability.

We do this to make crypto topics easier to understand for readers at all experience levels. AI does not draft facts, sources, or conclusions. Every article is reviewed and approved by a human editor before publication. Read our full AI Use & Content Policy.

Disclaimer: Cryip’s content is strictly for informational purposes and does not constitute financial, legal, or investment advice. Asset references are not endorsements, and readers assume full responsibility for any financial decisions.
Tags: BitcoinMSTRStrategy
Sathish Kumar Kaliraj

Sathish Kumar Kaliraj

Sathish Kumar Kaliraj is a crypto journalist and data analyst at Cryip, covering on-chain activity, market movements, and regulatory developments across the crypto industry. His reporting combines statistical analysis and blockchain data verification, drawing on certifications in data journalism, fact-checking (IFCN, Google News Initiative), and journalism fundamentals (NBC Universal Academy). His work has been cited by Coincu, Tech Times, and Bitcoinist.

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