As competition in the increasingly crowded generative AI space has intensified, it appears that OpenAI has turned to M&A to boost its offerings and stay ahead of its rivals.
OpenAI has already made six acquisitions in 2026, nearly as many as it made in all of 2025, according to Crunchbase data. Its latest purchase took place on March 19, when it announced plans to acquire Astral, a creator of open-source tools for software developers. This month, it also snapped up Promptfoo, an open-source tool for testing AI applications.
Overall, the San Francisco-based company has acquired 17 companies in the past three years, Crunchbase data shows. Eight of those purchases were made in 2025, although it didn’t even start making acquisitions until April last year.
By contrast, OpenAI only acquired two companies in 2024: Rockset and Multi, and one company in 2023: Global Illumination.
The company seems to be continuing its acquisitive streak this year. It announced three acquisitions in January alone, setting the tone for what appears likely to be a busy M&A year. In January, it acquired:
- Convogo, a consulting firm providing custom AI “solutions” and specializing in GenAI, predictive analytics and strategy.
- Torch Health, an AI-powered health app that aims to unify scattered medical records from hospitals, labs, wearables and consumers.
- Crixet, which provides LaTeX editing, error detection and team collaboration.
In February, OpenAI participated in an acqui-hire deal involving open-source AI agent OpenClaw and its creator, Peter Steinberger.
Historically, OpenAI hasn’t disclosed the purchase price for most of its acquisitions. The most expensive deal — at least among transactions for which a sales price was revealed — was its May 2025 acquisition of Io. OpenAI paid $6.5 billion for the then 1-year-old startup, which developed AI-powered devices.
However, not all of OpenAI’s proposed acquisitions have worked out. Last July, news broke that its planned $3 billion purchase of Windsurf had fallen apart.
Cash considerations
Certainly, OpenAI has deep pockets with which to buy companies despite reportedly being wildly unprofitable. In late February, the company announced it had closed a staggering $110 billion fundraising round at an $840 billion post-money valuation. The financing marked the largest startup funding deal ever, according to Crunchbase data. OpenAI’s investors involve a diverse bunch, including SoftBank, Nvidia, Amazon, Andreessen Horowitz, Sequoia Capital, TPG and Insight Partners.
Still, despite all that funding, according to a report from Fortune, HSBC projects that OpenAI’s cumulative free cash flow by 2030 will still be in the red, leaving “a $207 billion funding shortfall that must be filled through additional debt, equity, or more aggressive revenue generation.”
Startup M&A overall
OpenAI’s biggest rival, Anthropic, has been far less acquisitive. So far this year, it has made only one known purchase, buying Vercept, a 2-year-old software development startup. In 2025, Anthropic made two known acquisitions: Humanloop, an LLM evaluation platform for enterprises, and Bun, a JavaScript runtime for developing and managing web applications.
Overall startup M&A dealmaking has been fairly robust so far this year, Crunchbase data shows. This includes two deals in the multiple billions: Capital One’s $5.15 billion purchase of Brex and Eli Lilly’s $2.4 billion acquisition of Orna Therapeutics. The AI sector’s appetite for acqui-hires and smaller purchases of earlier-stage startups also continues to boost momentum.
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Illustration: Dom Guzman
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