So I have my actual directories that are linked to my plex server named very specifically. Most of my newly ripped content go in directories on my mac and PC named premove, then they go into a directory by date ripped. I have so many movies in those dated directories by how many I can get done per day, for the most part. I decided that premove didn’t really make much sense, because I had already moved them where they were going to go, so I changed the directory name to dates, but left everything else the same. So I went back to the Plex App (on my mac, which is what I primarily use to work with Plex) and relinked the folders, with the dates directory to their proper places on my Plex server. Once I got everything situated, every movie linked on my plex app/server that was linked to the new directory has a trash icon on it. I’m thinking I either missed a step somewhere or this is some sort of bug. Screen shot provided to show what I’m talking about.
Click on the Ellipsis on the right bottom of a poster and check if the file is a duplicate
Some are duplicates some aren’t.
Within that function you can delete the ones that are duplicate and unavailable. As for the other that are not duplicates and are NOT marked unavailable. The Plex Dance maybe required
They are all listed with trash icons, so no that’s not going to work. I’d be deleting my entire library. This is something else. Hence, why I’m thinking this is a bug…
It not a bug , move the Directory for the Library to somewhere safe and nuke the Library in Plex and start again is safest approach
You’ve got to be joking me. That is your suggestion?
Just to clarify here, it’s THREE seperate libraries, not just one, with a TON of differet media files, one that’s well over 24 terabytes.
edit 20 terabytes, sorry… 
Scan the entire library system.
Here’s what may have happened:
You have ‘Empty Trash Automatically’ correctly turned off - and your storage went missing when Plex went looking for it.
Trash can city.
Rescan and let Plex discover your items again.
Don’t sleep your storage.
Or don’t sleep your storage while Plex is doing maintenance.
Unless you find it entertaining doing this…
If ‘Empty Trash Automatically’ in enabled - you won’t see Trash Cans - you’ll see nothing. At least this way - a rescan is hopefully all you need.
It just kept getting worse and worse, so it was either a bug, or just didn’t like something I did. I went back and renamed all the folders premove and restored any pathways that I might have messed up. All is well in the shire. I would’ve liked to have made the changes, but it doesn’t seem to want to do that as or right now. Thanks for the help @JuiceWSA.
Find out what that was - and don’t do it…lol
As I said the safest method is recreate the Libraries from the start. Move your content directories out of harms way / well away from the path you gave in Plex and nuke / Delete the old Libraries that are empty now. Yes I know it’s PITA and will probably take all night.
No that’s just silly guy… That may be YOUR ridiculous method for fixing YOUR problems, which is just asinine, but for me, it just got confused because I changed a few directories around. I work in IT at a university, if our methods were just to “nuke” everything and start over, I’d be out of a job. I troubleshoot, find the issue, and resolve, that’s how you fix things. You use your silly methods, I’ll stick with my solutions.
edit
Fixed without “nuking”, the “easiest” solution. I cleared my cache on both my mac plex server and my windows plex server. Did a full rescan of both libraries, everything is back to normal. Thanks me! 
Ok, good for you. Glad you found your way, one of the fundamentals of life, as for being silly or not thanks for nappy comments.
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