So like most junior to mid level devs ;)

Claude does have this specific interface for asking questions now. I've only had it choose to ask me questions on its own a very few times though. But I did have it ask clarifying questions before that interface was even a thing, when I specifically asked it to ask me clarifying questions.

Again, like a junior dev. And like a junior dev, it can also help to ask it to ask / check what its doing "mid-way", i.e. watch what it's doing and stop it, when it's running down some rabbit hole you know is not gonna yield results.