I've always this attitude that the one after me should not face the same issues as I had and so I update all wrong documentation, this also helps me remember how stuff works. But I have had many occasions where I just had to give up. People thought I was being annoying, my PR for fixed Readme (or even a Readme at all at times!) were simply not picked up, etc, etc.
I left that company, and left a letter for management about the abysmal developer experience.
I prefer to think that updating the documentation isn’t fixing the root issue, and that the working systems are their own documentation if explained properly, so document in such a way that they can’t become outdated, when feasible.