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Recently, the Finder has asked me for a password whenever I move a file to the trash. I get the message, "Finder wants to move 'filename' to the trash. Enter your password to allow this". I checked permissions on ~/.Trash, and it belongs to me/staff with drwx------ permissions, as expected. This happens with any file I try to delete, and I have full permissions on the files I'm deleting. When I enter the password, the file is moved to the trash (and not immediately deleted) as normal.

This is on Mojave 10.14.6, and it started happening after I installed security update 2021-003 (though I don't remember if it started happening immediately after that).

Note that I can move files to the trash from a command line. mv blah.txt ~\.Trash works just fine (no sudo needed). It's only when I drag a file to the trash that I have problems.

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    You have permissions on the FILES, or on the DIRECTORY containing them? It's the directory permissions that matter, not whatever the file is set to.
    – Marc Wilson
    Commented Apr 28, 2021 at 21:17
  • Permissions on files and the directories they're in. And permissions on their parents, for good measure (though not on the root level of the startup disk, because Mojave doesn't like that).
    – the klaus
    Commented Apr 28, 2021 at 21:43
  • Please provide the output of ls -l@ for the filename and the containing directory.
    – Marc Wilson
    Commented Apr 28, 2021 at 21:50
  • Note that this happens for every file in every directory that I've tried. Here's a typical one: -rw-r--r--@ 1 me admin 163198 Nov 12 2015 my-file.txt com.apple.metadata:kMDItemDownloadedDate 53 com.apple.metadata:kMDItemWhereFroms 134 com.apple.quarantine 25 drwxr-xr-x 3246 me admin 103872 Apr 28 19:42 my-directory
    – the klaus
    Commented Apr 28, 2021 at 21:57
  • Also, note that it works from a command line (details added to original post).
    – the klaus
    Commented Apr 28, 2021 at 22:18

3 Answers 3

Reset to default
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Ah, I found the answer elsewhere among many suggestions for fixing trash issues: just delete the .Trash folder. I ran sudo rm -rf ~/.Trash and restarted. The .Trash folder was recreated, and now it seems to work just fine. Odd. I'm glad it's fixed, but I wish I knew why the fix worked.

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I ran into this problem using clean install of Monterey - being asked to enter password for every file or folder I tried to delete.

I realized that the native root folders (forgive me if this isn't the correct term - I'm referring to Desktop, Documents, Downloads, etc.) had permissions set for me as Read & Write and "everyone" as No Access. However, the contents I copied into that folder had additional users labeled "staff" and "everyone" both of whom had Read Only access.

I changed the permissions on the root folder (Desktop, Documents, etc), so that it applied to all enclosed items and that seemed to do the trick - I'm no longer being asked for password or fingerprint every time I delete something I previously created.

Folder permission changes

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You can reset User Permissions on your "domain"

In the terminal application you paste this command :

diskutil resetuserpermissions / `id -u`

Then you reboot the system in safe mode (press Shift key at boot) and reboot after.

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  • And what exactly does that do? It appears to be undocumented, and I'm reluctant to run it without some detailed information about what it does.
    – the klaus
    Commented Apr 28, 2021 at 21:44
  • You can see here : eclecticlight.co/2020/02/18/… I used this command very often without problems.
    – user415185
    Commented Apr 28, 2021 at 22:02
  • Yeah, I'd found that article, but it doesn't actually tell me what this is going to do to my permissions. Is it going to set everything in my home directory to standard default values (me/staff ownership with -rwx------ permissions)? Is it going to mess with ACLs?
    – the klaus
    Commented Apr 28, 2021 at 22:09

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