At what point do you bring a CYA (cover your a**) situation to leadership?

At other jobs, I have waited until I was leaving to provide them the documentation about everything to leadership. Other times I brough these concerns to leadership when I wanted to stay, it led to horrible retaliation until I did quit. I don't want to quit this job. I like it.
So when do I bring these issues to leadership without retaliation?

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If you don't trust your boss then you should probably be looking for another job, even if you like it (my conception of hell is as a place in which it is not rational for anyone to trust anyone else). Mind you, it might take a while to determine the extent to which your boss is trustworthy.

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