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BUSINESS · NOV 7, 2026

AI Law Firm Crosby Secures $5 Million Liability Insurance

Ryan Daniels secured $5 million in AI liability insurance for the law firm Crosby to enable autonomous legal work performed by AI agents.

Founder Ryan Daniels secured $5 million in AI liability insurance from Testudo to cover legal tasks performed by AI agents without human supervision at his firm, Crosby. The coverage addresses a critical gap in the insurance market, as many major carriers currently lack standard risk assessment methods for generative AI or are introducing exclusions for AI-related losses.

Crosby currently utilizes AI for approximately 20% of its workload, focusing on gray-area tasks such as applying playbook rules and document reformatting. Daniels stated that his goal is to achieve full legal work performed by agents without lawyers by the end of next year. This transition faces significant legal obstacles, including ethics rules and state laws that prohibit the unlicensed practice of law and mandate attorney supervision.

While startups like Harbor and the Artificial Intelligence Underwriting Company are emerging to provide specialized coverage, established insurers remain cautious. Evan Greenberg, CEO of The Chubb Corporation, noted that AI liability is an emerging exposure that has not been fully contemplated in casualty underwriting to date.


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Ryan DanielsCrosby Law FirmTestudo Insurance

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