F5 to Buy CalypsoAI for $180M to Expand AI Security Business

Seattle-based cybersecurity and application delivery company F5 is strengthening its artificial intelligence security portfolio with the acquisition of CalypsoAI in a deal valued at $180 million.

The transaction, which will be financed primarily with cash, is expected to close later this month, according to an announcement from F5.

Founded in 2018, CalypsoAI operates from offices in Ireland and New York City and specializes in securing enterprise generative AI environments. The startup provides real-time threat detection, AI infrastructure protection, and data security solutions for organizations deploying AI-powered applications and workloads.

The acquisition comes as enterprises rapidly adopt generative AI technologies while facing growing concerns about securing AI models, protecting sensitive data, and defending against emerging cyber threats.

“AI is redefining enterprise architecture — and the attack surface companies must defend,” said François Locoh-Donou, President and CEO of F5. He added that strengthening AI security capabilities remains a key priority as organizations continue expanding their AI deployments.

CalypsoAI has attracted significant investor backing since its launch. In 2023, the company raised $23 million from investors including Paladin Capital Group, Lockheed Martin Ventures, Hakluyt Capital, Expeditions Fund, and several others.

Commenting on the acquisition, CalypsoAI CEO Donnchadh Casey said the company’s customers depend on its platform to thoroughly test AI systems at scale, implement adaptive inference-layer guardrails as AI models evolve, and provide greater visibility and auditability across enterprise AI environments.

The acquisition reflects a broader trend of rising investment in AI-focused cybersecurity technologies. Funding for cybersecurity startups reached a three-year high during the first half of 2025, driven by increasing enterprise demand for advanced security solutions capable of protecting AI infrastructure.

For F5, the CalypsoAI purchase marks another strategic acquisition in a busy year. Earlier in June, the company acquired San Francisco-based cybersecurity startup Fletch, followed by the acquisition of observability company MantisNet in August, further expanding its security and infrastructure management capabilities.

The company has also continued to deliver strong financial performance. F5 recently reported fiscal third-quarter results that exceeded analyst expectations, with revenue rising 12% year over year to $780 million. GAAP net income increased to $190 million, compared with $144 million during the same period last year.

Investors have responded positively to the company’s growth strategy, with F5 shares gaining more than 30% so far this year.

By adding CalypsoAI’s enterprise AI security technology to its portfolio, F5 aims to strengthen its position in one of the fastest-growing segments of the cybersecurity market as businesses seek more comprehensive protection for their expanding AI operations.

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