From Control Boundary to Insurance Claim: Reconstructing AI-Mediated Losses Through the CER Framework

The rapid diffusion of agentic AI has created a new coverage problem for commercial insurance: some AI-mediated losses are now affirmatively insured, some create silent-AI exposure under legacy cyber, technology errors-and-omissions (E&O), directors-and-officers (D&O), employment practices liability (EPLI), crime, and media policies, and others are being actively excluded. This paper maps that emerging boundary by coding 55 AI threat classes against 26 insurance products, endorsements, and exclusion regimes using public carrier materials and OWASP/MITRE threat catalogs. We identify a four-tier insurability frontier: affirmatively insured perils, silent-AI exposures, actively excluded perils, and perils outside conventional private insurance structures. Our coding measures publicly claimed positioning rather than executed contract wording; the headline statistics describe what carriers publicly state about coverage, not what would be paid in any specific claim. Three patterns emerge. First, affirmative AI coverage is beginning to differentiate by primary risk emphasis: public materials often position Munich Re around model performance and drift, Armilla and parts of the Lloyd's market around hallucination and broader AI liability, Tokio Marine Kiln and CFC around IP and technology E&O concerns, Apollo ibott around emerging autonomous system liability, and Coalition around deepfake and AI-enabled cyber response. Second, legacy lines retain silent-AI exposure where AI is an instrumentality rather than the legal cause of loss. Third, foundation model concentration is the clearest genuinely novel insurability frontier because upstream model failure can correlate losses across many cedents at once; the relevant market design question is which insurability constraint each candidate structure relaxes, not merely which systemic risk template exists.

AI agents can now take irreversible actions in operational systems, but agent-caused losses are still not clearly assigned, priced, or transferred. Providers often disclaim consequential damages, users are left with uncompensated losses, and default human review limits the efficiency gains of automation. We ask when autonomous AI deployment can become economically acceptable despite failure risk. Our answer is to quantify risk at the customer-task-trace episode level and transfer it through insurance. Automation is acceptable when its expected benefit exceeds the premium, control cost, and remaining risk. This requires a defined role with bounded permissions and comparable traces. We introduce trace-economic underwriting, which maps tool-use traces to customer exposure and claimable loss, then uses this representation for pricing, control, and risk transfer. It uses deterministic economic labels rather than an LLM judge. In our trace-to-loss testbed, trace-economic pricing reduces pricing MAE from $17.7K to$569 and removes regressive cross-subsidy. A 300-trace expert audit accepts 295 labels unchanged. On 1,000 real SWE-smith traces, trace-conditioned controls reduce CVaR95 by 72%. Theorem~1 gives a finite-sample scope condition. We release code, labels, and audit sheets.

AI agents increasingly act through tools and delegated authority, but general incident repositories rarely capture the mechanisms needed to compare public failures with agent-security evaluations. We present the Agent Incident Registry (AIR) (Project page: https://enkryptai.com/air), a source-linked catalog containing 487 records of agent-related events disclosed from 2022 through 2026. Each record includes supporting evidence, a stable identifier, and missingness-aware labels for causal role, disclosure class, mechanism, and outcome. Among the 336 generative-system records in which the agent acted, 81 involved realized harm (24%). Realized outcomes concentrate in in-the-wild and safety-failure records, while responsible disclosures and research demonstrations are overwhelmingly demonstrated; the aggregate share therefore characterizes collection composition rather than deployment risk. After initial curation, a second human reviewer checked all 487 records and their existing labels for completeness and correctness. In a deployment-analogue audit, InjecAgent's 1,054 cases occupy three of AIR's twelve surfaces and are all attacker-triggered, whereas AIR contains 92 no-adversary safety failures. AIR supports source-grounded case retrieval and evaluation-scope auditing, not failure-rate or control-efficacy estimation.