Cannot delete files from downloads folder

Today my Mac began having an issue when attempting to delete any file found in my downloads folder. When I attempt to delete a file (actually, moving it to the trash) through the finder, I get the following error

"The operation can’t be completed because one or more required items can’t be found.

(Error code -43)"

I've attempted to repair permissions on my hard drive and still the issue persists, as well as boot my computer into recovery mode and running first aid on my Hard Drive.

However, when I go to delete a file via terminal, I can successfully do it this way.

If anyone can point me in the right direction I'd greatly appreciate it.