session.is_loggable() and GPG
When you open the window, there's no session yet - and thus session.set_loggable() isn't set. You can also see that the button shows wrong whether the session will be logged or not.
bct, what's your proposed fix for that? if not session: create_a_session()? This is definitely a problem as even with logging disabled, it could be logged until there's a session.