When iTunes doesn’t move deleted items to trash

check iTunes Preferences, the Advanced tab, the settings for “iTunes Media folder location” and “Keep iTunes Media folder organized“.

iTunes media folder preferences.
iTunes preferences for Media Folder and organization.  For some reason* the location had been lost as this field was blank.

If you have your iTunes library configured to keep everything under a preferred folder location and to let iTunes automatically organize the items in the library, then deleting an item should provide a prompt asking whether the item should be moved to the Trash or kept in the media folder.

iTunes move to Trash prompt.
  When media folder organization is enabled, iTunes should prompt when deleting items.

I recently noticed that iTunes wasn’t prompting to move deleted items to the trash anymore (resulting in left over cruft taking up disk space).  After checking several things, I found the preference settings had been lost.   After correcting (restoring) the settings iTunes did prompt to organize the folders and appeared to do a quick scan thru the media there (a couple minutes), but it finished quickly and everything seems to have returned to normal.
*I can only guess the setting problem cropped up a couple days ago when I had some problems with external USB devices and had to forcefully disconnect and shut everything down.

iTunes version 11.0.1 (12) on OS X Mountain Lion 10.8.2  iTunes Media Library is location on an external 1.5TB USB3 HDD.  I’ve been using external storage for iTunes for about 4 years now, so that of itself wasn’t the source of the problem.

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