When does AI start feeling like a helpful crew member?

A lot of AI products are starting to feel less like tools and more like some little shipboard crew member that talks back, guesses your next move, and sometimes just acts weirdly certain. That part feels fun right up until it doesn’t.

I’m curious where people draw the line between “nice sci-fi vibe” and “now I don’t trust this thing with real work.” Have you seen a product get better once the AI got more agent-like, or did it just get harder to predict?