Command-line interface (CLI) agents powered by large language models (LLMs) can interpret natural-language requests, plan multi-step tasks, execute shell commands, and modify files and system state. As these agents are increasingly used for operating-system (OS) workflows, it is important to evaluate whether they can be misused to carry out security-relevant operations. Existing benchmarks often lack an attacker-knowledge model grounded in tactics, techniques, and procedures (TTPs), provide limited coverage of end-to-end kill chains, rely on simplified single-host environments, or use LLM-as-a-judge for success evaluation. We introduce AdvCLI, an MITRE ATT&CK-aligned benchmark for evaluating OS-level misuse risks of CLI agents in a controlled multi-host sandbox. AdvCLI contains 140 tasks: 40 direct malicious requests, 74 TTP-based tasks, and 26 end-to-end kill chains. Each task is paired with deterministic hard-coded verification protocols that check whether the requested OS-level effect is realized. We evaluate seven CLI agents and products built on nine foundation models, including ReAct, OpenClaw, OpenAI Agent SDK, Claude Code, Gemini CLI, Cursor CLI, and Cursor IDE. Results show that current CLI agents frequently proceed beyond refusal and can complete a non-negligible fraction of malicious OS-level tasks, especially when requests include TTP-style attacker knowledge. AdvCLI provides a reproducible testbed for evaluating these risks and for developing stronger safety mechanisms for tool-using CLI agents in the future.

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