A screen should appear to the right of the Finder list that looks like the old sync screen in iTunes. 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).(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. For Podcasts, looks like you must add the podcast to your (cloud) library, then download the podcast. You cannot sync the older iPods from the cloud.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. 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. ALWAYS close Music and Podcasts applications on the Mac before attaching older iPods to the Mac.Refinement of observations, after several weeks of successful use with Classic iPod:
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