How do I delete a stubborn file in the Bin?

Assuming that the file tunnelBlick.tblk is in ~/.Trash, then one sure way of deleting this file is to boot to Recovery Mode, (⌘R when restarting the Mac), and then in Terminal (on the Utilities menu)... use the following command, e.g.:

rm -f /Volumes/Macintosh\ HD/Users/Your_Short_Name/.Trash/tunnelBlick.tblk

• The example command above assumes the main Startup volume is Macintosh HD, change as needed.
• The Your_Short_Name is that which you normally see in Finder as the name on your Home folder.

Then type reboot and press enter to restart the Mac back to normal mode boot.

NOTE: The rm command, especially with the -f option is potentially destructive if the target is not properly typed. Make sure the command is properly typed before executing. You can also first try without the -f option and the see if e.g.:

ls /Volumes/Macintosh\ HD/Users/Your_Short_Name/.Trash/tunnelBlick.tblk

Returns anything, and is so, then use the -f option.

Update: Based on the answer to the question I asked in the comment under your question, you would use the following command from Recovery Mode, (⌘R when restarting the Mac):

rm -f /Volumes/Macintosh\ HD/Users/Your_Short_Name/Library/CloudStorage/iCloud\ Drive/.Trash/tunnelBlick.tblk

With the same caveats applying:

• The example command above assumes the main Startup volume is Macintosh HD, change as needed.
• The Your_Short_Name is that which you normally see in Finder as the name on your Home folder.

Note: You can first try from normal mode:

rm -f /Users/Your_Short_Name/Library/CloudStorage/iCloud\ Drive/.Trash/tunnelBlick.tblk

If that doesn't work you can also try prefacing the command with sudo; however. if it will not delete from normal mode then boot to recovery mode.

Rather than putting in the trash, try putting it into the /tmp/ folder, like so:

mv -fv /Users/SHORT-NAME/Library/CloudStorage/iCloud\ Drive/.Trash/tunnelBlick.tblk /tmp/ 

The /tmp/ folder is cleared out on reboot, so that might do it.

First thing I would try is running this following command in Terminal

killall 'Finder'

Then once Finder quits, in a second or two, Finder should automatically restart. Then try going back to empty the trash.

If that does not work then I would attempt this...

Try restarting the computer in Safe Mode.

1. Start or restart your Mac, then immediately press and hold the Shift key. The Apple logo appears on your display. If you don't see the Apple logo, learn what to do.

2. Release the Shift key when you see the login window. If your startup disk is encrypted with FileVault, you might be asked to log in twice: once to unlock the startup disk, and again to log in to the Finder.

To leave safe mode, restart your Mac without pressing any keys during startup.

Safe mode (sometimes called safe boot) is a way to start up your Mac so that it performs certain checks and prevents some software from automatically loading or opening. Starting your Mac in safe mode does the following:

• Verifies your startup disk and attempts to repair directory issues, if needed
• Loads only required kernel extensions
• Prevents startup items and login items from opening automatically
• Disables user-installed fonts
• Deletes font caches, kernel cache, and other system cache files

^{Source: Use safe mode to isolate issues with your Mac}

Once your computer has rebooted into Safe Mode, then go ahead and try to empty your trash.