In 2026, cybersecurity evaluations involving OpenAI, Anthropic, and Google agents reached real systems outside their authorized test scope. The paths were different. OpenAI agents exploited research infrastructure, coordinated across runs, and compromised parts of Hugging Face's production environment. Anthropic reported cases in which a misconfigured third-party environment exposed real systems to agents pursuing simulated cyber tasks. In a separately reported evaluation, Google's Gemini accessed three real organizations through an unintended internet route; Google stated that the model stopped in all three instances. Taken together, the cases show why an evaluation cannot rely on an assumed boundary. That boundary must be verified while the agent is operating. This comparative instrumental case study develops a Proactive Agent Security Assurance Cycle (PASAC) and a five-layer Boundary Assurance Stack. The framework combines risk-tiered task design, executable scope contracts, pre-run validation, least-capability access, independent egress enforcement, credential restrictions, cross-run monitoring, automatic stop conditions, and evidence-based reauthorization. A leading-indicator model, nine design propositions, and seven falsifiable hypotheses turn these lessons into a testable research program. Because the public Gemini record is limited to attributed statements and journalism, its detailed causal mechanism remains provisional. The central conclusion is straightforward: proactive agent security requires continuous assurance across the full execution system, not confidence in any single sandbox or safeguard.

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