OpenAI is making a bold $3 billion move to expand its footprint in AI-assisted software development, entering advanced talks to acquire coding assistant startup Windsurf. But this high-stakes deal comes after a failed attempt to acquire a different rising star in the space: Anysphere, the company behind the popular AI coding tool Cursor.
Despite being an early investor in Anysphere via its Startup Fund, OpenAI reportedly tried — and failed — to buy the company in both 2024 and early 2025. Cursor’s fast-growing presence and reported $200 million in ARR had made it a logical acquisition target. But with Anysphere now said to be raising at a $10 billion valuation, those talks fell through.
In contrast, Windsurf’s ARR is estimated at $40 million, but the startup offers OpenAI something potentially more valuable in the short term: a quicker path to scaling an integrated coding assistant that’s already in the market.
OpenAI’s recent launch of Codex CLI, a command-line AI coding agent, underscores its ambition to dominate the developer tooling space. However, the acquisition push signals that it’s not waiting for internal products to catch up to market leaders like Cursor or GitHub Copilot.
For OpenAI, Windsurf may not have been Plan A — but it might be the fastest way to get into pole position.