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Continuous Underwriting: Why “Once a Year” is Broken

calendar_today June 11, 2026 person Rajeev Gupta domain cowbell

As I drove to work this week, a reminder popped up to tell me that I need to book in for a service. This made me think about how the insurance industry has treated cyber; you wouldn’t drive a car relying on a service certificate from 1995 to tell you if your brakes work today. […] The post Continuous Underwriting: Why “Once a Year” is Broken appeared first on Cowbell .

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