Anthropic and OpenAI now have a combined annual recurring revenue (ARR) of more than $115 billion, reportedly approaching Microsoft’s roughly $150 billion annualized run rate in its Productivity and Business Processes segment. Their combined run rate also exceeds the trailing-12-month revenue of SAP, Salesforce and Adobe combined. Anthropic has posted the sharper increase, with ARR rising from approximately $9 billion at the close of 2025 to $47 billion by mid-May 2026, based on TickerTrends data and ARK Invest analyses. Estimates put its run rate between $65 billion and $75 billion by the end of July. OpenAI’s ARR increased from an estimated $20 billion to $25 billion at the end of 2025 to around $40 billion to $41 billion by July 2026, while internal reports indicated monthly growth above 20% in July. Enterprise AI adoption has moved from experimentation toward operational use, driven by multi-year contracts, workflow integration, coding and productivity applications, agentic products that handle complex software development tasks, and rising API demand. However, gross ARR may overstate the revenue reaching the companies because products are distributed through Amazon Web Services, Google Cloud and Microsoft Azure under revenue-sharing arrangements. Anthropic and OpenAI closed major funding rounds in 2026 and are widely expected to be preparing for potential IPOs. Investors are likely to focus on margins, retention rates and the durability of enterprise contracts rather than headline ARR when S-1 filings eventually arrive.