The iTunes Conundrum.

This is one of my very first iTunes purchases. If you’re not seeing the image above, I’m referring to “What Did I Do To You?” by Lisa Stansfield. It’s the original album version, which encompasses the complete “vision” Ms. Stansfield had for the track. It was purchased in 2003 using my old iTunes username (I don’t think we called them Apple IDs back then). I’ve been looking for the track for ages and was deleted when I finally found it on a backup CD-R with “2004 backup” scrawled in Sharpie across the label side of the CD.

Eager to listen to this track again, I fired up an old iMac and imported the file into iTunes. I was prompted for the password of that forgotten account. Unbelievably, I remembered the password. The file was imported successfully but with a few caveats.

* iTunes Match wouldn’t recognize the track
* I couldn’t add it to a playlist
* The track would propagate to my other Apple devices. No iPhone, no iPad, No MacBook Pro.

I ended up copying the file by hand, using Dropbox, to my MacBook Pro. I imported it there as well after going through the password rigamarole.

Hunting around in Finder, I found the actual file and discovered that it was an m4p file, Apple’s old proprietary format that has DRM (Digital Rights Management) built into it. I converted all of my m4p files to m4a years ago using the iTunes Match service. The track is apparently not available in Apple Music today, as I can only find the edited down 7-inch version. Clicking on “Add to My Library” makes iTunes crabby.

I really want this song to be included throughout my Apple devices. It’s suppose to “just work”, right? Does anyone know how to get this song to become part of a playlist in iTunes? How do I convert it to a friendlier format without spending $40 on a piece of software that I’m going to use only once?

I know that I’m a huge Apple geek, but I’m at a loss on this one. If you have any suggestions (other than telling me to get Windows or something), please feel free to leave a comment. I’d love to hear from you.