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My media are taking most of my internal hard disk drive. I wanted to know if there is a way to automatically transfer music that I do not listen to regularly on my iTunes folder to an external hard disk.

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Steps to perform this:

  1. Navigate to the location you want to copy the files to and leave the window open in the Finder.

  2. Create a smart playlist in iTunes by Option-Clicking the new playlist button in the bottom left of the main window.

  3. Configure the playlist with the appropriate criteria, such as: {Last Played} {is before} {1/1/2008} or whatever you consider "Old." Click Ok

  4. Select Edit, Select All and drag the items to the folder you opened in step 1. Wait for the copy to finish and you'll have all your old music in that folder.

  5. To automate the process, use Automator and configure a new workflow similar to the following image:Automator Workflow Configuration

  6. Rig up the workflow you just created to run. Put it in the dock, use Crontab or run it at login.

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interesting. thanks for that, however, I dont see how this would be done automatically. If a smart playlist could be able to store all its contents in a particular directory - my problem would probably be solved –  Newton Apr 3 '12 at 16:47
    
@Newton, the answer refers to use of Crontab, which is a system job-scheduler that is set through the command line. You can set a job to run at any interval(s) you'd like (once a day, week, whenever). This sets you up to have automatic transfer. –  soxman Apr 4 '12 at 4:37

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