> they will never, ever suggest writing a tool to make their own life easier, get more accurate information, or anything

Make sure you process doesn't depend on anyone reading your mind.

When I run into things like this, it becomes a one-liner in my instructions/harness or in the canned prompt/skill I use that sets off a process.

In this case, I instruct agents to proactively build/improve diagnostic tooling if it would help them with their task + if it meets a bar of generalization/reusability (else it should be an ephemeral probe that gets abandoned at the end of the solution).