Why do I keep getting "unable to locate original file"?

...and then when I click "locate"...I can't find them...please help.

When you originally put the music into iTunes, it didn't copy them into the iTunes media folder. Now, it tries to play the song from the original location, which would be gone if you used an external storage device. Before you import more song into iTunes, make sure you go to edit>preferences>advanced, and make sure the box is checked next to "Copy files to iTunes Media folder when adding to library" and you shouldn't get that message for any music you add after that.

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