[josephorjoe]

Depends on whether or not the boss can be trusted.

I've had bosses where the only thing they ever heard from me were optimistic status updates on work in flight.

I considered them completely untrustworthy -- one for lack of competency and one for being a clumsy power seeker.

But in general I would only talk to my boss about issues that (1) I'm OK with my boss telling other team members that I said what I said about it, (2) I'm OK with my boss having input on what course of action to take on the topic, and (3) I trust that the conversation is unlikely to be interpreted in some negative way for me.