Upload in Plug-In Not Working

I have been trying to upload PDFs to a group library for awhile, and have tried syncing multiple times and it looks like the library is properly synced (I can see all the documents in the library), but when I try to click on the add button in the plug-in, it is greyed out and won't allow me to upload anything. Is this an administrator issue, or is something wrong with my plug-in?

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