The music on your iPod is stored in a Music folder inside a hidden folder called iPod_Control. The easiest way to get at it is using the terminal. For that to work, 'disk mode' must be enabled for your iPod.
First, connect the iPod to your computer. If you're running Catalina or newer, open a Finder window and click on the iPod entry under Locations in the sidebar on the left. If there are two entries for the iPod, click on the one with the icon that looks like an iPod. Now, in the General tab look in the Options section and make sure that
Enable disk use is checked. If you're running an older OS, launch iTunes and then click the (tiny) iPod icon in the topbar and make sure the
Enable disk use box is checked. You should now see a disk icon corresponding to your iPod on the Desktop. If you don't see the icon, eject the iPod, unplug it and then plug it back in.
Now open a terminal by using Finder to navigate to Applications. Double-click the Utilities folder, then double-click Terminal.app to launch the terminal. In what follows you'll be using terminal commands to copy the contents of the iPod's Music folder onto your Desktop and unhiding the contents so that you can import them into either the Music or iTunes apps. In the attached screenshot, I'll show the terminal's prompt as a single dollar sign '$' but your prompt may look different, as may be color of your terminal. Double-check your typing before you hit Enter on each command.
The 'mount' name of the iPod will probably be 'iPod' but we need to make sure using the 'ls' command:
If the name is something different for you, you'll have to substitute that name for 'iPod' in what follows.
Now you'll execute several commands to copy the contents of the iPod's Music folder to your Desktop and then change the attributes of the files to make everything visible. This is required before you can import the music. iPods are slow devices communicating over slow USB connections, so the copying part (the 'cp' command) can take quite a while.
Code:
cp -r /Volumes/iPod/iPod_Control/Music ~/Desktop
chflags -R nohidden ~/Desktop/Music
xattr -rd com.apple.quarantine ~/Desktop/Music
xattr -rd com.apple.FinderInfo ~/Desktop/Music
After the 2nd 'xattr' command, you should see the Music folder appear on the Desktop. Now you can import everything. To import into Music.app, use the File -> Import... menu to navigate to the Music folder on your Desktop, then click Open. To import into iTunes.app, use File -> Add to Library... to navigate to the Music folder on your Desktop, then click Open.
If you already have music on your computer, something to be aware of is that the possibility of duplication. You can avoid that by holding down the Option key when you launch Music or iTunes and then creating a new library to hold the music from your iPod.
Hope this helps. Let us know how you get on.
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