The Insurance Gap That AI Created

Agentic systems make decisions in sequence. Each step stays within the configured parameters. No isolated action would fail an internal audit.

The problem shows up in the chaining: a series of individually "correct" decisions produces an outcome that no one anticipated and that doesn't fit the taxonomy of your policy. The system operated exactly as it was programmed, no person made the decision that caused the harm, but the harm happened anyway.

This creates a classification problem that most corporate policies can't resolve. The "technical failure" category requires that the system operated outside of what was expected. The "human error" category requires that someone clicked in the wrong place. The agent did both things right and produced the wrong result: a case that was left out when the contract was drafted.

And here's the point few discuss openly: the coverage gap wasn't created on the day the harm happened. It was created on the day the system went into production.

Your legal team, your broker, and your liability policy were calibrated for a risk model that no longer has the shape they know.

Every company moving autonomous agents into production needs to have this conversation before go-live: who is legally accountable when the outcome is generated by a sequence of autonomous decisions that worked exactly as planned?

The honest answer, at most companies today, is still silence.

Have you already had this conversation with legal and insurers before pushing an agent into production? Tell me in the comments.