OpenAI Eyed Cursor Before $3B Windsurf Deal
OpenAI’s Strategic Shift in AI Coding Acquisitions
Before pursuing its $3 billion acquisition of AI coding platform Windsurf, OpenAI reportedly explored buying Anysphere, the creator of popular coding assistant Cursor. This revelation comes as the AI giant aggressively expands its foothold in the competitive code generation market.
Why Cursor Was a Natural Target
OpenAI had existing ties with Anysphere through its Startup Fund, which participated in the company’s 2023 seed round. The relationship made Cursor (often used interchangeably with Anysphere) a logical acquisition target. According to CNBC, OpenAI approached Anysphere twice – first in 2024 and again in early 2025 – but negotiations ultimately failed.
Instead of selling, Anysphere is now pursuing funding at a staggering $10 billion valuation, as reported by Bloomberg. This valuation reflects the explosive growth of AI-powered coding tools and Cursor’s impressive $200 million in annual recurring revenue (ARR).
The Windsurf Alternative
With the Cursor deal off the table, OpenAI turned its attention to Windsurf, which generates about $40 million ARR. While significantly smaller than Cursor in revenue, Windsurf represents a strategic acquisition that would immediately boost OpenAI’s position in the developer tools market.
This move comes alongside OpenAI’s release of its own Codex CLI agent, an open-source coding tool for terminals. However, the Windsurf acquisition talks suggest OpenAI isn’t willing to wait for organic adoption of its in-house solution.
The Bigger Picture in AI Coding
The failed Cursor negotiations and subsequent Windsurf discussions highlight how critical AI-powered coding assistants have become for major tech players. As developers increasingly rely on these tools, companies like OpenAI are racing to control this high-growth sector through both internal development and strategic acquisitions.
With Cursor continuing to operate independently at a premium valuation and Windsurf potentially joining OpenAI’s portfolio, the AI coding assistant market is entering a new phase of consolidation and competition.