Can't import into i-tunes

I have nearly 140 Gb of MP3 music on an external hard drive. When I import the songs onto i-tunes they appear in the library, but when I play them (with the Ex HD still attached) i-tunes says it does not know where the file originated from, then prompts me to find the file...every time.
Has anyone else had this problem...? What am I doing wrong?

Id say your importing the song which is moving it off your external. When you goto File>Import this moves or copies the song from its current location to the "iTUnes Music Folder" which by default is on your internal drive inside "My Music".
When you goto File and pick "Add file/folder to library" this option will keep the song in its current location and basicly tells iTunes where its located on your system so it can "Add" it to the iTunes database/library

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