iPod Classic sync with macOS Catalina???

Side bar is recognizing my iPod classic but the second its connected it says its syncing but nothing is happening, just spinning. Left on even over night and still the same. I even selected some playlists to add and the apply button still is grey'd out. I have to force quit it to eject the iPod. Any help???

Posted on Oct 8, 2019 9:21 AM

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Posted on Jan 16, 2020 2:05 PM

Refinement of observations, after several weeks of successful use with Classic iPod:

  1. ALWAYS close Music and Podcasts applications on the Mac before attaching older iPods to the Mac. Looks like Finder (which does syncing with pre-iOS iPods) may have file or other conflicts with Music and/or Podcasts applications for syncing pre-iOS iPods. For older iPods, do not change sync settings in these applications (only change in Finder); looks like changing older iPod settings in these apps may cause locks/problems.
  2. You cannot sync the older iPods from the cloud. For Podcasts, looks like you must add the podcast to your (cloud) library, then download the podcast. (Did not test the subscribe to podcast route.) For Music, if you download or create MP3s, you must add these to the (local) library using command O.
  3. Once you are ready to sync the legacy iPod from the Mac, close the Music and Podcast applications, attach the iPod to the Mac using a USB cable, open Finder, scroll down to Locations, and TAP on the first (of sometimes two) iPods shown in the list (not the eject button on the list). A screen should appear to the right of the Finder list that looks like the old sync screen in iTunes. There should be a sometimes brief display of arrows spinning on the list entry you just tapped (this display appears over the eject button). For me, if I wait about 45 seconds, the sync arrows then appear on the iPod for a short time (remember, the older iPods have relatively slow CPUs). When the arrows stop spinning on the iPod, press the eject button on the entry in the finder list.
  4. If problem persists, verify you've selected "automatically sync when iPod is connected" and "enable disk use" under the general tab of the iPod in Finder. Verify under the Music tab that you've selected "sync music onto iPod" and "entire music library". When I selected "sync music onto iPod", there was an inaccurate error message that said I would replace the contents on the Mac with those on the iPod (should have indicated that I would replace the contents of the iPod with those on the Mac).
  5. An oddity I've seen is that the Podcasts I download from the Podcast application appear under both Music and Podcasts on the iPod. Formerly, these appeared only under Podcasts on the iPod. Hope this is rectified in the next update, but I can live with that for the present.

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iPod Classic sync with macOS Catalina???

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