Anthropic's annual recurring revenue reached $30 billion in May 2026, exceeding OpenAI's $24 billion ARR for the first time, per industry reporting summarized in the State of AI: May 2026 update. The crossover comes roughly 18 months after OpenAI was running 5× Anthropic's revenue. Both numbers are run-rate annualizations of the most recent reporting period; neither company has formally disclosed audited annual results.
The interesting math is the trajectory, not the cross. OpenAI's ARR has roughly doubled in 18 months. Anthropic's has grown roughly 6× over the same period — accelerating into the lead through enterprise sales, particularly the financial-services agent rollout from earlier this week. The split between the two companies' revenue mix is what readers should watch: OpenAI is more weighted toward consumer ChatGPT subscriptions and general API; Anthropic is more weighted toward enterprise contracts with longer sales cycles and stickier deployment. The latter mix is structurally less volatile — but also has lower upside on a unit-economics basis. Crossing on top-line is one milestone; gross margins, retention, and customer concentration are the metrics that will matter when both companies eventually disclose audited financials.
If you're allocating compute budget across model providers, the ARR shift is a leading indicator of platform momentum, not yet a quality signal. Make the technical decision on your benchmarks; use the financial decision (commercial terms, contract flexibility) to pick whichever vendor's commercial team is hungrier this quarter.