Cloudflare proposes $2.18B private offering of convertible senior notes

Cloudflare is looking to raise $2.18 billion through a private placement of convertible senior notes. The proposed deal targets qualified institutional buyers under Rule 144A, continuing a financing playbook that the San Francisco-based company has now run three times since 2021. A familiar financing strategy, scaled up Cloudflare has developed something of a habit when it comes to convertible notes. The company first tapped the market in August 2021 with a $1.125 billion offering of zero-coupon notes due 2026. It returned in June 2025 with a larger $2 billion offering of 0% notes due 2030. This latest proposal, at $2.18 billion, represents another step up the ladder. The notes would be structured as senior unsecured obligations. If history is any guide, they would carry little to no regular cash interest. The “convertible” part means holders can eventually exchange the notes for Class A common stock at a predetermined price. Cloudflare currently has approximately $1.29 billion outstanding on its 2026 notes and another $2 billion on the 2030 notes. Those 2026 notes are set to mature around August 15, 2026, which means a significant chunk of debt is coming due imminently. What $2.18...