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Time machine backups filled my 4TB external HD. To free space, I deleted a handful of the particular backups from:

/Volumes/Winston's 4TB/Backups.backupdb/  

Those files ended up in the trash bin and trying to "empty" the trash bin erred indicating the folder was in use. So, I deleted the contents through terminal:

cd /Volumes/"Winston's 4TB"/.Trashes/
sudo rm -rf /501/2018-0*

Finder now shows the trash bin being empty, but the space has not been freed up on the drive. How do I recover that space?

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    Has the trash finished emptying? – jmh Sep 15 '18 at 22:02
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    The ACL for Time Machine won’t let these rm commands simply work, so either we don’t have the full story on how it was modified or that drive filesystem structure is broken and needs a repair or wipe so that emptying trash and calculating space work as designed. – bmike Sep 15 '18 at 22:13
  • Deleting the files directly, either by dragging them or using sudo rm is not the proper route. There is a tmutil command designed for interacting with them, and tmutil delete is what you would have wanted. Check out this answer. – Mike Williamson Jan 9 at 19:54
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Enter Time Machine - there is an icon on the menu bar. Scroll back using the arrow keys on the screen until you get to the older backups. Near the top of the window, there is an icon that looks like a gear. Click on this icon and one of the options in the pull-down menu is to delete. Use this to delete backups.

  • why the downvote! My answer is correct. – jmh Sep 17 '18 at 17:34
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I never have patience to repair permissions or delete files piecemeal on Time Machine since the hard links take significant IOPs when you have lots of backup intervals - especially on a spinning drive and not an SSD.

I typically just put the drive on the shelf if I ever need any data and buy a new drive for current backups when I can’t zero the entire filesystem.

Worse, if you didn’t use tmutil delete to remove the files, you likely broke the drive for future use with Time Machine and didn’t correct for the access controls that prevent even root from using rm to delete or modify the backup files.

To zero the filesystem, use Disk Utility to remove the entire volume or repartition the whole drive. Be very sure and unmount all volumes physically disconnecting them when you wipe a drive, there is no undo and the data goes “poof” once you confirm the operation.

  • so now we know you are an impatient man :) – Ruskes Sep 15 '18 at 22:06
  • My patience for a disk repair is 36 hours lately - longer if I’m being paid to be patient or if I’m going to learn something cool at the end of the experiment. – bmike Sep 15 '18 at 22:08
  • so now we also know your loyalty can be bought :) – Ruskes Sep 15 '18 at 22:11
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    Yes. Kindness and cooperation are the coin of the realm. I love your attitude and hope everyone loses patience with gaslighting, unkindness, bike shedding and such. – bmike Sep 15 '18 at 22:14
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    No, but if you pick a small backup, it should complete in 20 minutes to prune a recent backup @josh you can use tmutil compare to check the difference between the two most recent backups. Then delete the latest version - those will check the health of a small delete. If 5,000 changed files can’t delete in 600 seconds, there’s something seriously wrong. You’d need to know what changed, though to know if hours to delete is bad. If you filled 4 TB in weeks, you might just have corruption in the catalog and need to wipe – bmike Sep 16 '18 at 2:27

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