Great point! If you alias pip to pipask in your .*rc file, than this should already work out of the box for some tools, but there may be problems such as the need for non-interactive flows and configuring failure thresholds.

I'll think about this use case more!

It occurs to me that if people are executing pip over requirements.txt outputs it would work and be very helpful, but if they're giving LLM agents shell access directly probably the main problem is going to be finding a way for pipask to try to confirm that it's talking to a human and not just the LLM again (impossible in general but still)... probably out of scope though!

Seconding this use case! I see pipask helping greatly as another safety net when using coding agents.