With Dumbledore's withholding information and plans, there's also another factor that has to be considered in HBP.
Dumbledore is dying. Even if he isn't assassinated by Death Eaters, he's on borrowed time and he knows it. And when the curse on that ring finally offs him, every bit of intelligence that he kept to himself is lost forever, and every plan that the intended executors haven't been fully briefed on becomes useless.
He may be Leader of the Light today, but everyone can see that there is a not-too-distant tomorrow when he won't be, and he has not enacted any sort of transition to make sure that his successor will be able to hit the ground running. Failing to do that in a war when the top man being a casualty is always a possibility is foolish. Not doing it when the top man is already terminally ill is outright idiocy.
A big part of the problem with Dumbledore is that he believes that he understands the prophecy and that Harry is therefore
guaranteed to take down Voldemort in some manner.
Thus he's basically ignoring that whole aspect of the conflict because as far as he is concerned, it will sort itself out, so he's focused entirely on maneuvering things into position to deal with the aftermath of that. He's also very worried that Harry will be a repeat of Voldemort and Grindelwald and turn 'dark', so he's more focused on making sure that doesn't happen than he is on trying to make sure Harry actually succeeds.
And then oops he gets himself hit with an incurable death curse in a moment of weakness.
So now Dumbledore is trying to salvage his elaborate and over-complicated plans with the knowledge that he's
not actually going to be around to oversee everything in the aftermath, and right in the middle of all this chaos suddenly a pair of teenagers are knocking over dominoes and throwing said plans into even more chaos.
Unsurprisingly, Dumbledore finds this to be very upsetting and in typical human fashion he's focusing on the source of the upset rather than taking a step back and realizing that there isn't anything useful
to salvage from his plans, and that he does not in fact possess the power to shield the children from the consequences of their actions anymore. (Dumbledore is a
huge believer in children having the opportunities to make mistakes without suffering severe long-term consequences for such, even when realistically they absolutely should. It's why he's so obsessed with protecting Malfoy; he feels that Malfoy has made what
should have been a minor error in judgement normal for a child and will now have the rest of his life destroyed because of that, which in Dumbledore's mind is a truly horrible thing indeed.)
It is very common for the kind of person that makes elaborate plans to, when the table gets flipped and everything goes to shit, waste huge amounts of time and effort attempting to make the plans work anyway in a form of sunk cost fallacy. Even though he
knows intellectually that one of the key foundations of his plans (the fact that he will be around to see them through) has been destroyed, he's invested so much time and effort into the plans that he's still trying to figure out a way to make them work anyway, and he does not appreciate a couple of teenagers with less than a tenth of his experience trying to tell him he's wrong, especially when they're right.