Transferring old music from your iPod to MacOS

Context

I grew up in a music town. Nashville is to musicians what LA is to actors. It was fun to find not only my old iPod but discover it still played music. This 5th gen iPod had been powered off for ~5 years. Yet, the iPod fired up without hard drive clicks and still played music. The nostalgia wore off as I had to repeatedly pull out wired headphones to listen to albums purchased at shows decades ago. Many of which who either broke up long ago or songwriters whose early albums never made it to streaming.

Apple originally limited the ability the ability to transfer music from an iPod to a computer in an effort to fight piracy. The days before Sean Parker was an established VC and philanthropist. I was happy to find a post on the MacRumors forums that provided a set of CLI commands.

My setup:

• 5th generation iPod

• MacOS Sequoia, 15.2 Beta build 24C5073e

Pre-requisites:

• Attach iPod to Mac via USB

• Launch Finder → iPod (Finder replaced iTunes long ago)

  • Verify sync disabled

  • Verify disk mode enabled

• Launch preferred terminal: CMD + Space “terminal” for MacOS Terminal

Transfer steps via terminal:

1. Verify iPod mounted as disk:

ls /volumes

My output:

(base) ryanconley@Ryans-MacBook-Pro ~ % ls /volumes
IPOD        Macintosh HD

2. Copy the contents of your iPod’s Music folder to your Mac’s desktop. This step will take time to load as the data transfer speed is limited by the iPod’s antiquated USB speeds. This step took ~40x minutes for me but your results will vary. Note, this folder will not show up yet on your desktop.

cp -r /Volumes/iPod/iPod_Control/Music ~/Desktop

3. Remove the MacOS hidden file flag attribute on the newly copied Music folder. Note, this folder remains hidden until step 5.

chflags -R nohidden ~/Desktop/Music

4. Remove the default MacOS extended quarantine attribute. Security note: Use caution, this is my personal iPod that only had files synced from my iTunes with purchased albums of days past. My security risk was low. Your mileage may vary

xattr -rd com.apple.quarantine ~/Desktop/Music

5. Remove default MacOS extended attribute for Finder metadata. The Music folder will appear on your desktop after this cmd.

xattr -rd com.apple.FinderInfo ~/Desktop/Music

6. Import into Apple Music:

   1. Launch Apple Music: CMD + Space “music”

   2. Import Music folder: CMD + O → Select newly copied “Music” folder

      *Note iCloud took a considerable amount of time (hours?) to complete. During this time, these Artist & albums reflected on my iPhone, but I could not play the music.

   3. Optional: Authorize your Mac’s Apple Music app for your iTunes. It had been years I needed this step but it was commonly used in the days pre-streaming.

Summary:

A brief effort of four CLI steps allowed me to bring decades old from home town artists into my music library. iCloud further enables me to stream these albums on the go. Now I can enjoy music from iPhone at home and on the go. Enjoy!