Item on legal hold and item getting deleted:
Enterprise Vault Product enhancement request:
If someone deletes email on hold only stubs get deleted. Once hold is lifted, the previously deleted emails will not be deleted and will only expire when retention is reached and can only be deleted with Archive Explorer Currently, when a stub is deleted, but the "DoDelete" function, (a delete request sent back to the archive), fails for any reason, that function will not occur again. In your case, since the items were on legal hold, the deletion failed on purpose since EV couldn't allow the deletion to occur.
Now that they are no longer on legal hold, the user can delete them at will, but the user will have to do it from the web tools, ie Search, Archive Explorer, etc. This is because the user no longer has a shortcut in the mailbox that can be deleted, which would fire the afore mentioned "DoDelete" command, since it is already deleted.
I would like to asking for a "Delete Orphaned Archived Item" setting. A setting like this could look at all the shortcuts in the mailbox and match them up with the archive items. If an archived item doesn't have a corresponding shortcut, delete it.