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steve333

macrumors 65816
Original poster
Dec 12, 2008
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I'm frustrated. When I upgraded the OS to Catalina and Apple for some reason decided to change iTunes to Music all of my songs that were not purchased but added to my iPod Classic from my CDs are gone.
How do I transfer the entire Music library from my iPod back onto my Mac Mini? I don't want to lose them if something happens to my iPod.

Music is so confusing now also, you enter search but it doesn't search the iTunes Store unless you click on it afterwards. Then you have to figure out how to buy it, you can't buy the entire wishlist at the same time and it asks for your password every time. Apple is supposed to be good at making software easy to use but this is really bad. I can't be the only one who thinks this.

Anyway, any help would be greatly appreciated
 
I’m not sure if this helps but back in the day I used a program called Senuti to transfer music off any iPod ... not sure if it works with Apple Music though (one of the main reasons I have not upgraded from Mojave)
 
I'll check out Senuti
That link about iTunes doesn't work with iPod Classic
 
This seems like what I need, however as I try to install, I get an error message that there is a problem. I am on Mojave.
 
If you turn on hidden folders in your OS you should see a Music folder on the iPod in Finder. (This works 100% in Windows anyway, haven't tried in macOS but I'm sure it works the same) You can just drag this into iTunes/Music and it should bring everything over intact. Just note that the file names themselves are changed when put on the iPod, so if your song doesn't have artist/album info the name might be nonsense.
 
If you turn on hidden folders in your OS you should see a Music folder on the iPod in Finder. (This works 100% in Windows anyway, haven't tried in macOS but I'm sure it works the same) You can just drag this into iTunes/Music and it should bring everything over intact. Just note that the file names themselves are changed when put on the iPod, so if your song doesn't have artist/album info the name might be nonsense.
How do you turn on hidden folders?
 

These commands might help, weird that shift+command+. did not work.
 
I found something called imazing, a free download but I think it only allows 100 songs to be transferred from the iPod to Mac. I'm going to try it a little later
 
I had the same thing happened. I found my iTunes library on my back up and transferred it to the computer. I got my songs back but a lot of the art work is a mess. For some reason anything that the computer was unsure about (and there was a lot), it just replaced it with Frank Sinatra’s Christmas. Sigh.
 
I tried imazing, the free version only allows 50 transfers but the interface was nice and simple so I paid $45 for a lifetime license. It worked, very easy to use yet very slow.
Still, it was worth it.
 
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