On Lion 10.7.3, when trying to empty the Trash from the GUI the items to be deleted are counted, and the the dialog doesn't progress anymore:

Emptying the Trash...

Stopping emptying the Trash doesn't help much either: the only thing changing is the status on the dialog that now reads Stopping...

It's reported that resetting the PRAM does the trick, and I know that I can just force the removal from the CLI, but can somebody help me understand why this is happening and how to fix it?

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    If you are interested in what application misbehaves enter "lsof | grep .Trash/" in Terminal. – bot47 Jul 13 '12 at 14:09

A program that is accessing files in the Trash that you're trying to Empty could interfere with attempt to Empty Trash.
The resulting timeout causes the "Stopping…" (which takes forever) alert message that you saw.

You can turn off Time Machine and try again or perhaps reboot (after turning off Time Machine) and see if the trash empties properly before starting up Time Machine or whatever other programs might have files open.

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  • [1] Restarted, unchecking Reopen windows when logging back in. Didn't work => it's not the actively running apps. – Marius Butuc Mar 15 '12 at 14:06
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    [2] After turning off Time Machine, emptying the Trash completed successfully! – Marius Butuc Mar 15 '12 at 14:08
  • Turning off Time Machine worked for me as well – dsteele Apr 16 '12 at 2:07

You could also try this:

  1. Open Terminal from /Applications/Utilities

  2. Run command: rm -rfv ~/.Trash/*

This should delete all files in the trash and show you what it's doing as it goes.

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  • At least on my drives in Lion, the Trash directory is .Trashes. – cam8001 May 13 '12 at 20:14
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    @cam8001 I believe it's different for external volumes vs. local user directories. – Matt Love May 13 '12 at 23:36

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