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Why won't my library auto/manually update?

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For the last couple weeks, my server hasn't been updating and I do not know why. I have reinstalled a couple of times and am still running into the same issue. Just noticed it a couple of days ago when I tried to watch something that was added to my library a week ago.

I've also deleted some items off of the Server and they won't remove, nor will the library itself when I try to delete it. Keep getting an error message showing that an error occurred.


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