Risky-Bench: Probing Agentic Safety Risks under Real-World Deployment

Large Language Models (LLMs) are increasingly deployed as agents that operate in real-world environments, introducing safety risks beyond linguistic harm through tool use, external transactions, and multi-step decision making. Existing agent safety evaluations construct risk-oriented tasks that lack a hierarchically organized taxonomy of attack surfaces, rely on predefined harm categories rather than deployment-grounded safety rubrics, and evaluate agent behavior in isolation rather than during realistic, long-horizon task execution. To address these limitations, we propose Risky-Bench, a deployment-grounded framework for systematic agent safety evaluation in life-assist settings. Risky-Bench derives context-aware safety rubrics from domain-agnostic safety principles and systematically probes safety risks across hierarchically organized attack surfaces through realistic task execution under varying threat assumptions. Applied to life-assist scenarios covering food delivery, in-store assistance, and online travel booking, Risky-Bench evaluates seven state-of-the-art agents across 750 tasks, revealing attack success rates ranging from 25% to 60% and exposing systematic failure patterns including threat-model-specific vulnerabilities, attack-surface-dependent risk concentration, and model-dependent effects of explicit reasoning. Our code and data are available at https://github.com/SophieZheng998/Risky-Bench.