How can I make iTunes sync with an old iPod Shuffle?
Does anyone know how to make iTunes communicate with and list what is on an old working waterproof iPod Shuffle, so the music can be updated?
[Re-Titled by Moderator]
You have to connect it using its charging cable (headphone jack to USB) and it should show up in iTunes (Windows/pre macOS 10.14) or Finder (macOS 10.15+). Just click the iPod icon and then Songs. Every song should be listed there.