Gemini CLI at work has the same issue: it'll prefer hacking your workstation over just asking you how to proceed.
I think the harnesses are setup to have a bias to action otherwise the LLM would just stop all the time when doing trivial task but it also mean they'll keep going when the "obvious" path is to just prompt the user.
I often tell it to stop asking me and just keep going until it accomplishes X task; unfortunately it tends to assume I want something that only just barely works, in the sense that it means it's time to stop once its there, which is I don't think a harness by itself could easily address (ultimately the model itself needs to determine the stopping points unless I literally specify by hand hidden evaluation criteria).
That's why think it's at least partially a training issue where the model gets rewarded for "solving" the problem within a certain amount of context/time without access to grounded knowledge (eg looking up the actual spec for a format) nor adversarially/rigorously evaluated against a reviewer capable of finding all the edge cases/shortcuts preventing something from being a properly generalized solution. I don't want it to ask me for guidance when it's working on a well-specified problem, I want it to either find the right parser and use it, or to completely implement one against the spec, rather than write some half-assed string inserter that eg only works on the specific select statements my examples use right now. My understanding is that the Mythos/Fable models were better trained for this but from my brief foray into using Fable for work I wasn't that impressed. For me they need to get better at agentic search and self-eval still
Having a reliable shared memory for hundreds of agentic AI users is something that's 95% snake oil at the moment. There are a few successes on an individual level (I really like Hermes[0]) but nothing scales to a company level easily.
It should be possible to (pre)configure all agentic harnesses used in a company to use a single source for information so that it'd automatically pick up internal libraries, conventions, licensing decisions etc and remember them across sessions.
I've had limited success with this on a personal level, but it's still not ingrained in the model because it would really need a custom harness. Hooks, skills, prompts get you like 80% of the way. I still need to do a "please check that the project matches the conventions defined in ..." regularly to catch any drift - especially on more vague stuff that can't be locked down with unit testing.