By Joel Dare - Written August 12, 2026
Under Finder > Settings > Advanced there’s an option to Remove items from the Trash after 30 days but it’s not working on either of my MacBooks.
I want the trash to take care of itself.
When I open Trash, switch to View > As list and then sort by Date added, I find very old dates.
In order to see the Date added column, I had to add it. I did that under View > Show view options, and then checked Date added. I’m assuming this is the date the file was added to the Trash and not the date it was added to the disk as there is also an option for Date created.
On my MacBook Air, however, I found that the oldest item in the Trash was July 30th. So, today, by the time I looked at it, it’s up to date. And my storage space is showing ~150GB free of my ~500GB hard drive. So, maybe I fixed this a few days ago.
On the MacBook Pro, where I was looking at this just yesterday, the problem persists.
I did two more things to try to correct it. First, I deleted more old files, leaving about 45 days’ worth. That cleans it up but leaves a few extra files so I can see if it “catches up”. Second, I opened Settings and unchecked the Remove items from the Trash option. Then I closed the dialog. Then I opened it again and checked it again. Hoping that toggling this back and forth causes it to “reset”.
My own machine is making a liar out of me, but I’m not crazy. My work machine still shows the behavior. I probably fixed this on mine and it just took a little time for the files to correct.
On this machine, my personal one, I don’t know what fixed it.
On my work machine, I deleted about 6 months of files that shouldn’t have been there. The oldest files in the Trash. I also deleted three downloads that looked “stuck” but didn’t show up in Safari. Safari wasn’t open.
The bottom line seems to be that macOS will stop on any error in the trash and silently fail. So, manually deleting a few old files seems to kick it in the pants and get it going again.
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