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I can download episodes in Apple Podcasts.

I can connect the iPod nano (4th gen, cable only, no internet) and use Finder to open sync settings. The manual podcasts selection shows the feeds, but none of the new episodes.

When I hit Sync, I get an error popup Some items, including “<...>”, were not copied to the iPod “<my> iPod” because they could not be found.

How do I get it to sync the new episodes?

The history is a bit complicated. The ipod was working fine with an older MacOS and iTunes, but the computer finally died. I got a new macbook and restored from time machine. Initially, it was updating new episodes, but there were two entries for each feed in the Podcasts app, and on the ipod each episode appeared twice - or sometimes more, they seemed to breeding. So I started removing one of the feeds, sometimes both and resubscribing. Now I can download new episodes in the podcasts app, (but it won't download new ones for me), but they don't appear in the ipod sync settings.

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2 Answers 2

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Partial answer:

Manually copying files into the old itunes podocasts folder will get file onto the device; the ipod will sort them into shows.

This still stinks for getting new episodes and removing played episodes, especially since you can't really tell from the garbage filenames which is which.

Apple podcasts folder:

~/Library/Group Containers/243LU875E5.groups.com.apple.podcasts/Library/Cache

iTunes media folder:

~/Music/iTunes/iTunes Media/Podcasts/Unknown Podcast

In theory I could break them out into folders other than Unknown Podcast, but limited information is available. Some have cover images, and some have data if I enable the Author/Title fields in the finder columns. Others are mysteries.

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Thanks @Justin. In my initial state, the 'finder sync' window shows in finder when I mount the 6th gen iPod nano, but it had only general, music and photos tabs. I'm on Sonoma 14.4.1. I don't have iTunes installed.
My system did not have the iTunes Media and below folders, so I created them. Note that you have to backslash before any spaces (see commands I did below) Then I copied one mp3 from the Apple Podcasts folder. They aren't named so you can't tell which is which, so I just picked one. The commands below copy the first mp3 it sees (assuming there is one there). I ejected my 6th gen iPod nano. When re-mounted, it had a podcasts tab and knows about those that I subscribe to, allowing me to sync those podcasts now -- easily. I'm not sure if copying the mp3 was required. Once it did sync, the podcasts icon was disabled on my iPod Home Screen so I had to enable that in the iPod settings app; what I don't know is -- had I added the app to the Home Screen first, would the 'finder sync' have shown the podcast tab?

commands:

mkdir ~/Music/iTunes/iTunes\ Media
mkdir ~/Music/iTunes/iTunes\ Media/Podcasts/
mkdir ~/Music/iTunes/iTunes\ Media/Podcasts/Unknown\ Podcast
cd ~/Library/Group\ Containers/243LU875E5.groups.com.apple.podcasts/Library/Cache
cp `ls *.mp3|head -n 1` ~/Music/iTunes/iTunes\ Media/Podcasts/Unknown\ Podcast
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  • If you have a new question, please ask it by clicking the Ask Question button. Include a link to this question if it helps provide context. - From Review
    – help-info.de
    Commented May 18 at 20:07
  • Huh? My answer clarifies Justin's suggestion. It specifically tells you how to sync an older iPod to a newer OSX without iTunes. It looks like a bot is trying to judge a human here.
    – jpa57
    Commented May 18 at 23:14

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