This is probably similar to 1000s of other threads asking for help transferring the iTunes library to an external drive. I've done my searching and i just can't get it to work .. I have my collection of music in my "Music" folder on my mac, but i'd like to move all the music to an external drive. The folder on the external is "External/Music". I've transferred all my music over to the external drive, i go into iTunes and point the location of music collection to the new folder on the external drive (Preferences >> Advanced >> Change button) I try to play some songs in iTunes and they're all broken links :s Here are the settings in the advanced tab i don't have "keep itunes music folder organized" checked, i don't have " copy files to iTunes music folder when ..... " checked either. I suspect the problem is because iTunes doesnt organize the music for me, and i refuse to let it do so. I've got a certain way that i organize my music, which is not the same as how iTunes does it. For this reason, the music is not actually in the "Music/iTunes/iTunes Music" folder but just in "Music" as i mentioned above. I'd like to keep the music organized the same way i have it now on the External; not let iTunes organize it for me. Has anyone run into this problem before and know how to get around it?