In iTunes when I press "add to" playlist I get an error message, but I can still drag and drop the song into a playlist

Why is this happening and how can I resolve it?

I called Apple Support and they walked me through it. They told me to basically copy and paste my music to the external hard drive. (I think.) Or maybe it was they had me transfer a folder to the EHD. I don't exactally remember it was a few years back. But I tried to plug in the EHD before starting and...nothing. Still says same thing, "locate file."

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