This item will be deleted immediately. You can’t undo this action.

Hey there! Hopefully this can help.

It sounds like the user permissions may need to be reset. Previous comments are accurate, if sudo rm-rf (Drag trash here) didn’t work, and the fact that it works fine in a different user, it may be user permissions.

Also said earlier the process has changed and I believe done using Terminal from recovery mode, (Start your Mac holding Command R, hit Utilities > Terminal), I believe it is, (From recovery mode now),

repairUserPermissions or resetUserPermissions, can’t recall right now, but each command is safe to use, one just might not be recognized....then select a user who’s permissions to reset

I do know the old way works too though, (Not through the old Disk Utility, but through the Home folder info),

Only difference is you may have to allow Terminal to be accessed by the whole system:

System Preferences > Security and Privacy > Privacy > Full Disk Access, add Terminal and put a check next to it,

Then open Finder > Go > Home, press Command I (i), reveal Sharing and Permissions by clicking the disclosure triangle,Hit the gear icon then “Apply to enclosed items”, then “OK”,

Once that box disappears you can open Terminal from Applications/Utilities and enter:

diskutil resetUserPermissions / `id -u`

Once that completes, restart and test. Hopefully that fixes it!

Otherwise it might be possible Finder Preferences aren’t working as expected, In Finder > Preferences, what do you see there in Advanced, or General, (wherever the options for Trash are nowadays). Gate Keeper may also be playing a role. Anyhow if resetting permissions doesn’t work let us know!

techprame Said:

"This item will be deleted immediately. [...]All of a sudden, the recycle bin has stopped working and now I get this following message: [...]I have no idea what to do in this situation.[...]"

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Have you reinstalled the macOS?:

Though an issue pertaining to just one user, it might just fix it for all.

How To Reinstall the macOS:

1. First, Back up your Mac:

Create a Time Machine backup of your Mac, so that you can have something to restore your Mac from, should anything go wrong with the reinstall.

2. Then, Reinstall the macOS:

Nothing would be deleted. It's just that items that have become corrupted or deleted, would be replaced or reinstalled back to where they should be. Go Here: How to reinstall macOS from macOS Recovery - Apple Support

Another way it may go in recovery is either:

resetHomePermissions, or

repairHomePermissions,

Forgive me, I can’t recall right now, but I do know, as said before, the old way does work still also.

That said, booting to safe mode and attempting to empty the trash is a good step, (Despite it working fine in another user).

Also a good place to find a culprit is in Login Items, (System Preferences > Users and Groups > Login Items),

All of these programs that are checked are opening every time you log in and could potentially be causing the troubles. I’d remove them (Highlight the hit the “-“), restart and test if all the previous steps did not work.

Here’s the article for safe boot/mode:

https://support.apple.com/en-gb/HT201262

Hope it works out!

You might try the following:

Open the Terminal in the Utilities' folder and paste the following at the prompt:

    sudo rm -Rf ~/.Trash

Press RETURN. Enter your admin password when prompted. It will not echo to the screen. Press RETURN again.

If you have no success with this, then try:

Fix permissions on Trash folder

Select your Home folder and press COMMAND-I to open the Get Info window. Be sure you have "read & write" privileges in the Sharing & Permissions panel. Check under "General" panel to be sure it isn't locked. If that is correct, launch the Terminal in the Utilities folder, and at the prompt copy and paste this command:

mkdir ~/.Trash

Press RETURN. If you get a message that the folder already exists, copy & paste this command:

sudo chown $UID ~/ .Trash

Press RETURN. Enter your admin password (it will be invisible) Press RETURN again. Then copy and paste this command:

chmod u+rwx ~/.Trash

Press RETURN. Log out and back in, or restart.

I’d back up the user, delete, and migrate the contents back in.

There is (was) a diskutil resetUserPermissions command around, but all references to that disappeared recently, which implies it might have had issues.

Yup, I’m aware thanks. One of many to get lost in the ether recently. I do know the method from recovery mode is the way to go moving forward though, but from what I’ve seen, given the weird symptoms corrupted permissions can cause, it still works okay. Who knows what Big Sur will bring, curious to find out though.

Another way to possibly fix this is by rebuilding the user account, it sounds tedious, but is fairly easy, of course I’d still recommend keeping a TM backup, etc.

—Log into another admin user.

—Delete your main user from System Preferences > Users and Groups.

—Be sure to select the option to “Keep a copy of the home folder”.

—Open Finder > Go > Computer > Macintosh > Users > Deleted Users, and remove “Deleted” from the username, then move back into Users folder.

—Re-create the user in Users and Groups, making sure to use the same username (Home folder name), and password. (And choose administrator if it was one).

—Create the user, when prompted select the option to “Use the existing folder”, done.

—Restart and login to your original user, I’ve had success with this method in the past with issues that are specific to just one user as well.

Note that you’ll probably have to re enter your Internet Account passwords just once to re authenticate. Cheers.

See this article, How to stop OS X from deleting trashed files immediately | Macworld

FWIW, the Apple doc around resetUserPermissions all disappeared not that long ago, and which is not an auspicious sign.