Help me rescue my treasured music from an ancient iPod

April 7, 2016 12:12 PM

I lost hundreds of mp3s when Apple installed their Music app on my iPhone. I thought they were gone but then I realized they're still living on the the original iPod I have kicking around (we're talking the white click-wheel iPod). Help a non-techie seize his last chance to save his long lost musical loves!

These were songs that I had downloaded almost 20 years ago (I stupidly didn't have them backed up anywhere at the time...I know, I know). Concert bootlegs mostly. What's the best way to make sure I can pull them off the iPod and into my current iTunes Library? Will my Mac just ask me if I want to import the music files? I know this might be a simple fix, but I'm a little paranoid about losing the last copy of these files and want to make sure I get it right.

posted by dry white toast to Technology (8 answers total)

The old method as to make a new, empty iTunes library, then connect the iPod and when the computer asks to link it up, tell iTunes not to overwrite the iPod but instead allow it to zap your [empty!] library. But that's based on years-old memories, and recent developments may have rendered it obsolete. :7(

I remember that you could get to it as mass storage, but the MP3 files deliberately had their names scrambled (which required a lot of listening or a piece of software to re-label).

Bummer, I totally sympathize. (Also, those old click-wheel iPods are awesome, and I wish I could get mine to recognize the Chinese CF card-reader I shimmed into it after the hard drive failed.)
posted by wenestvedt at 12:15 PM on April 7, 2016

Senuti used to be the goto tool for this, and an old version might very well work with your old iPod (assuming you can find a version that'll run on an Intel Mac).
posted by Alterscape at 12:16 PM on April 7, 2016 [2 favorites]

Try Senuti. The first 1000 songs are free.
posted by infinitewindow at 12:16 PM on April 7, 2016 [2 favorites]

If all else fails: Enable hard disk mode on the iPod using iTunes. Change Finder to show hidden files and open the ipod_control/Music folder on the iPod, which is where it stores the music. Drag these to your Mac's hard disk. Then disconnect the iPod. The rescued files won't have sensible names, but assuming they are well-tagged, iTunes will fix that when you re-import them.
posted by kindall at 12:24 PM on April 7, 2016 [3 favorites]

I have done this! My method works great!

I have an old click-wheel 1st gen iPod that I still use on a daily basis, but I gave up iTunes long ago (and use a Linux computer with it, to boot). Instead I use a charming little free software called CopyTrans Manager. The beauty of this thing is that it does two-way and has nothing to do with iTunes. It literally just copies files, back and forth as needed, by folder or artist, and with none of that metadata and erasure nonsense that iTunes is so fond of.

What's that, you say, you'd like to move that music from your iPod and put it back in your iTunes database? No problem, just copy it off the iPod and then into wherever you keep your iTunes folders, then add to your database.
posted by epanalepsis at 12:25 PM on April 7, 2016 [6 favorites]

I've had success with SharePod in the past. (Note that you want to download the free SharePod 3, not the "new" SharePod 4. The original author got bought out and they make it hard to find the original free software.)
posted by leo_r at 1:02 PM on April 7, 2016

1: Are you totally sure the music is gone from your phone? The updated Music app should not have erased any music stored in your device, although it might have tucked it in a new spot in the app (the better for Apple to promote their streaming service...) Try going to Settings > Music and unchecking Show Apple Music at the top. Then head back to the Music app and see if your stuff is under My Music.

2: I've used Senuti to good effect, though personally prefer iRip and iExplorer for this (just did the same thing for a friend a couple days ago using iExplorer). Side note: I do not personally recommend starting in iTunes and allowing it to overwrite your library as mentioned upthread.

Good luck!
posted by churl at 12:34 AM on April 8, 2016

I have done this with an old iPod several times by using Winamp, including late last year. Download and install winamp, index the iPod, copy the files to your hard drive (which I remeber as being very easy, just drag and drop I think), delete winamp. Done.

Don't mess around with iTunes, that's asking for trouble.
posted by shelleycat at 4:14 AM on April 8, 2016