So, I used Retroactive to install iTunes 12.9.5 which works with them all. Monterey won't sync any of them properly. I have three old iPods, a 4th gen Photo, a 2nd gen Nano, and a 7th gen Nano. So, it appears that I'm totally dead in the water as far as using this iPod Nano 6th gen device under Monterey. I can't be sure, but I think it did show up there prior to restoring the firmware. When I open the Music app the iPod doesn't show up there, either. All I get is the button to Check for Update and the button to Restore iPod. Now when I reconnect the USB cable the iPod still shows up, but there are no little tabs/links to do ANYTHING with it. I waited ten minutes, then clicked the other iPod entry in the sidebar that had an eject symbol. It downloaded 12 MB of an update, seemed to install, although the window said "updating iPod" for far longer than I thought it should take. So I dutifully clicked on the "Restore iPod" button in the Finder display. I read a posting in this section of the forum that suggested that you had to factory reset an iPod to get it to work properly under later versions of MacOS. Right clicking in the empty list did nothing. I simply could not figure out any way to get podcasts transferred to the iPod - I couldn't drag them from the Podcast app, nothing. I think that there was button to choose podcasts, but when I clicked on it there were no podcasts to choose - this was true, even though opening the Podcasts app shows the podcasts that I'm following. I mostly use this iPod for podcasts when I clicked on the podcasts link it changed the Finder window display to show an empty listing of podcasts. Originally when I did that it showed me choices in the window to the right: General, Music, Podcasts, and maybe one other (Pictures?). I plug it in, and it shows up in the sidebar of Finder. I am mystified about whether Monterey even supports this 2010-era device. It connects via USB and a 30 pin connector cable. I have an iPod Nano 6th Gen, the small square one with a display that clips on your clothing. Hi, so I'm trying to get used to MacOS Monterey (I know, late to the party).
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