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.
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.