0
Red-team an agent's system prompt for failure modes before deployment
Act as an adversarial reviewer of this agent system prompt before I deploy it. I don't want a rewrite yet, I want you to find how it breaks. Given the system prompt and the tools/capabilities the agent has, do the following:
1. Find at least 5 concrete inputs a real user (not necessarily malicious, could just be an odd but plausible request) could send that would produce an outcome the prompt author almost certainly didn't intend. Show the actual input text.
2. For each, trace why the current prompt fails to prevent it: is it a missing rule, an ambiguous rule, or a rule that conflicts with another instruction in the prompt.
3. Separately, find any instruction in the prompt that's unenforceable as written (the model can't actually verify compliance, e.g. 'never make up information' with no grounding mechanism to check against).
4. Rank findings by how likely a real user is to hit them (common but unintended use) versus how bad the outcome would be if hit, and don't rank a low-probability, low-harm issue above a high-probability one just because it's more interesting.
5. Do NOT propose fixes yet unless I ask; the point of this pass is finding gaps, not patching them prematurely.
System prompt: system_prompt
Tools/capabilities available to the agent: tools