Emptying Trash and copying files hang when end of progress bar is reached.

I have a late 2009 iMac running High Sierra (10.13.6).

I recently started having issues where emptying the Trash would hang when the progress bar reached the end. The cancel button would not work, and the only way to get rid of the progress indicator was to kill and relaunch Finder. The operation would be complete after this.

I then started to noticed that I was having issues copying files as well. Same thing. Progress bar hangs in a full state and can only be gotten rid of by relaunching Finder. However, in this case the operation has rarely been completed once Finder relaunches. This is much more inconvenient.

On the other hand, moving files does work without a hitch, which I find particularly puzzling.

I tried running First Aid from Disk Utility. I tried resetting permissions with a Terminal command. And I reviewed the permissions of the Trash in the Get Info window, and it appears to be correct. Not really sure what to try next, and I can't find any issues like this one online (probably because keywords flood me with more common Trash and file copying issues).

This issue appears to exist across all users on the machine. I even recently cloned my HDD using Disk Utility to a new SSD, and the problem continued to persist on the new drive as well (which isn't terribly surprising). Definitely open to suggestions here.