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Jonr515

macrumors 6502
Original poster
Nov 11, 2017
349
145
Midwest!
Every time I empty the trash this window is up. This time there were a few small files, if I hit the "X" the trash is empty. Any idea what causes this?
Screenshot 2023-01-29 at 1.33.31 PM.png
 
That usually happens when a large number of files is in the trash.
You could try to delete ~/.Trash and log out.
If you have external drives connected, delete the Trash folders from them too.
 
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When you get the indication in post 1 above...

Click the "x".
Open the trash.
What is IN the trash?
 
OP stated that in the example, there were a few small files in Trash. Presumably that means he checked it before selecting Empty Trash. He then stated that he clicked the "x" and then the Trash was empty.
 
I recently came upon this problem. On Ventura - but a Google suggests this is not limited to that OS. I'd get the 'Emptying the Trash...' window as above, but then it would just stay there, while clicking the [X] would complete action and close window. Just as you describe.

Anyway, one of the searches suggested going to System Settings > General > Login Items > Open at Login. Make a note of what is in that section (so that you can add them back later, if necessary), and then try deleting one at a time, with a reboot between each. Then try to Empty Trash as normal (I created a doc and then move it to Trash just for that purpose). If it works as expected, you may have found the culprit.

I got lucky with first guess - turns out it was a Dropbox login that caused the problem. Not sure why. I know there had been 'improvements' made to Dropbox recently, but I'm happy to kill it off at login. Interestingly (or maybe just coincidentally), one of the Google threads I found was saying that it was a OneDrive login causing the issue. So maybe these cloud service links are the first thing to look at here?
 
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