F5 to Acquire CalypsoAI for $180 Million

F5 to Acquire CalypsoAI for $180 Million

Security and application delivery solutions provider F5 on Thursday announced plans to acquire AI security firm CalypsoAI for $180 million.

CalypsoAI has developed a platform designed to use agentic red teaming, real-time defenses, and automated security enforcement to secure AI at inference (ie, while the AI is in a live, operational state).

Specifically, CalypsoAI’s platform can provide adaptive protection against prompt injection and jailbreaks, while also detecting and preventing sensitive data leakage from AI systems. 

F5 plans on integrating these capabilities into its Application Delivery and Security Platform (ADSP).

All shares of CalypsoAI, a company based in Ireland and the United States, will be acquired by F5 for $180 million, mainly in cash. The deal is expected to close later this month. CalypsoAI has raised over $40 million prior to its acquisition.

“Enterprises want to move fast with AI while reducing the risk of data leaks, unsafe outputs, or compliance failures,” said Donnchadh Casey, CEO of CalypsoAI. 

“Our customers rely on us to pressure test AI systems at scale, set inference layer guardrails that adapt as models change, and to gain visibility and auditability across their AI estate. F5 and CalypsoAI are more than the sum of their parts: high performance application delivery and AI security that enable businesses to deliver innovation faster without increasing risk,” Casey added.

F5 announced several other acquisitions this year, including MantisNet, Fletch, and LeakSignal.

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SecurityWeek’s cybersecurity M&A tracker, which includes monthly summaries and detailed annual analysis, lists additional deals.

Related: Mitsubishi Electric to Acquire Nozomi Networks for Nearly $1 Billion

Related: SentinelOne to Acquire Observo AI in $225 Million Deal

Related: Cybersecurity M&A Roundup: 27 Deals Announced in August 2025


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Security researcher and threat analyst with expertise in malware analysis and incident response.