Insurtech: Cyber Insurance Provider Cowbell Introduces AI enabled Collection of Capabilities Leveraging Language Models

Cowbell, the provider of cyber insurance for small and medium-sized enterprises (SMEs), launched MooGPT – a collection of new capabilities built using large language models and proprietary data.

MooGPT uses reinforcement learning techniques “to deliver a real-time conversational experience to appointed agents and active policyholders throughout the policy lifecycle.”

MooGPT reportedly “augments Cowbell’s AI-powered underwriting assistant, Moo, designed to underwrite similar risks and bring precision to risk selection and pricing.”

MooGPT assists brokers and policyholders in “getting on-demand guidance on risk assessment, such as Cowbell Factors and Cowbell Insights, non-binding premium indications, and provides information on the claims process.”

MooGPT assists policyholders “with security awareness, incident response planning, risk improvement recommendations, Cowbell Academy content, and incentives from Cowbell Rx marketplace.”

MooGPT adds “to Cowbell’s existing AI-powered capabilities that are core to delivering adaptive cyber insurance,” including:

  • Cowbell Factors, a set of proprietary risk ratings that continuously benchmark organizations against a risk pool of 35 million entities;
  • Cowbell Scanners, automated bots that collect and normalize hundreds of signals from the internet-facing footprint of an organization;
  • Cowbell Insights, individualized cybersecurity recommendations automatically generated for SMEs to help improve cyber risk posture and strengthen cyber resilience;
  • Cowbell Connectors and the modeling of over 3,000 risk signals collected from Microsoft 365, AWS, Google Workspace, Google Cloud, and other commonly used technology and cybersecurity solutions;

As noted in the update, Moo, Cowbell’s AI-based underwriting assistant, “automatically underwrites similar risks based on a collection of rules that evolve dynamically with cyber threats.”

Moo also “equips underwriters with granular, organized insights that streamline risk selection and pricing for more complex risks.”

Rajeev Gupta, co-founder and CPO at Cowbell, said:

“Generative AI is a transformative technology with the promise to bring higher efficacy to the cyber insurance ecosystem. With MooGPT, our broker partners and policyholders will benefit from increased productivity and efficiency gains. MooGPT further enhances Cowbell’s quoting, binding, issuance, and risk improvement experience.”

MooGPT will be “available to appointed brokers and active policyholders this summer.”

As covered, Cowbell claims it is “a pioneer of Adaptive Cyber Insurance, a leader in providing small and medium-sized enterprises (SMEs) coverage adaptable to today’s and tomorrow’s threats and the advanced warning of cyber risk exposures.”

In its AI-based approach to risk selection and pricing, Cowbell’s “continuous underwriting platform, powered by Cowbell Factors, compresses the insurance process from submission to issue in less than 5 minutes.”

Cowbell is “backed by 20 prominent leading global (re)insurance partners and serves SMEs in 50 U.S. states and the District of Columbia.”

Founded in 2019, Cowbell is “based in the San Francisco Bay Area with employees across the U.S., Canada, India, and the UK.”



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Disclosure Quest

Reg A - Form 1-A Filings Beta

Beta. Initial Form 1-A only. Target raise is the stated Amount to be Raised, totaled. Compared with the same dates one year earlier.

YTD: Jan 1, 2026 - Oct 26, 2026 vs Jan 1, 2025 - Oct 26, 2025

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Number of Filings131Prior 126 +4.0%
Target Raise, Total$3.40BPrior $3.54B -3.9%
This YTDYear priorChange
Filings 131 126 +4.0%
Target raise $3.40B $3.54B -3.9%

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