How do I sync my iPod Nano in Catalina? Sync options unavailable in Finder or Podcast apps!

The only work around I have found is this:

Open Apple Music. For some unknown reason Apple Music has a section called "Devices" on the left hand option bar. Your iPod should show up there, click on it.

It will only initially come up with the music options for syncing to your iPod. Instead of doing that, click on the button "Sync Settings..." in the upper right hand side of the screen.

This will make the Finder pop up with the right syncing interface for the iPod - why? I have no idea..

Hope that works for you!

I found the answer on a thread for syncing the iPod Classic in Catalina. You need to restore your iPod to factory settings then sync to your Mac. This worked for my Nano. The only problem I'm having is that it will only download the most recent, unplayed podcast episodes, even after I changed the settings.

I resolved syncing an iPod Nano 3rd Generation with a click wheel on Catalina which means that Catalina does support the device and most likely everything released afterwards.

Before I say what I did, try the following: Boot with the iPod plugged in and open any folder and see if the iPod appears in the sidebar. If so, click on it (the iPod icon that looks like the iPod, not the second icon that looks like a disc or SD Drive) and see if it loads/syncs in the window. After doing what I did, (to be explained below) it would not sync and load for me if I plugged it in after I had booted in Catalina but if I booted in Catalina with it plugged in it would sync and load and allow me to add and remove songs in the finder widows in Catalina. So try simply booting in Catalina with the iPod connected at the time of booting and then immediately accessing the iPod thru the Finder as explained above. if it doesn't work, do the following and then try booting in Catalina with it connected:

What I did before simply booting with it connected to Catalina:

I booted under Mojave. I reset the iPod to factory settings. I put my library back on it using iTunes. Then I booted under Catalina with the iPod connected and it worked. If I then ejected the iPod and then pulled the cable out and then plugged the cable back, Finder would show the iPod but it would not sync and load. But if I rebooted with the cable in connected to the iPod, and then immediately opened a window and clicked on the iPod icon, it would sync and load in Catalina. All of this begs the questions, did I ever need to reset and resync under iTunes in Mojave or is getting it to work under Catalina simply a matter of having it connected when it boots and immediately using finder to access the iPod and sync.

Good luck

I use iMazing to sync and manage my iOS devices now instead. The free version gives you some functionality like backing up. Sometimes you can find the software on sale for a discount via some of the online shareware discount stores.

I have no connection to the company, just a happy user of it. I use it to manage my iPod Classic to my iPhone 8 and more.

I "solved" my iPod syncing issues by going back to my old Mac and Sierra...10.12.6. It works like I expect and it put my iPod back in a familiar configuration.

Having to plug in my iPod before turning on the computer is a needless hassle. It seems Catalina is a work in progress.

I have the same problem that many are reporting - syncing ipod Nano with Catalina. The instructions given above do not work for me. The ipod is there in Finder - but clicking on it just shows a blank ipod screen with no details about syncing or anything.

I think Ipod touch may work - but the nano does not seem to. This is very frustrating - its either a **** up by Apple or its deliberate. Either way - its disappointing

When I try to sync my 8th generation iPod Nano with my 2018 iMac, the iPod shows up as a drive. Rather than giving me the options of adding media, it allows me to add files and shows voice recordings. I unplugged and replugged it in several times, but this did not appear to work. I went to the help screen for media synchronization in Finder, and it said that manual synchronization was no longer possible on Catalina, to answer another posed question.

Maybe this is obvious to users, but when you ask for help at official Apple Support for Catalina>Nano, they try, but they also remind you that it's been a while since Nanos were supported. Several agents tried. My little quirk is that after I update my 7G Nano from the new Catalina apps, the screen tells me that it can't eject my iPod because some of its files are in use. So I just drag the Nano icon into the trash. Seems to work so far.

BTW, the new interface screens for the podcast app are very time-consuming. More trouble to edit than the old iTunes. Why do we have to have icons for each podcast sub, which can't be converted to simple editable lists? And 2 clicks instead of one for deleting podcasts? Do this a dozen times a day, it adds up.

Had the same problem! Very frustrating, especially that my ipod now doesn't distinguish between songs and podcast and doesn't remember at what point I was in the podcast if I swap to another, play music or sync. Just did the latest update from Apple and they still have NOT fixed the problem. Very poor customer care...

Thank you ... my problem is syncing playlists to a Nano. Your workaround worked, but then the next time I opened the Nano the playlists were gone again. Also, Catalina does not let the Nano remember that I checked "Manually manage." I have to re-enter it each time I open that screen.

Another odd bit along this line -- I'm getting a checkbox that says I can mange manually, and I check it, but the nxt time I open the screen the box has been un-checked. Anyway, right now my Nano 7G is syncing music/podcasts/audiobooks ok because I cut out one of my big files of music as an experiment. It seems that what took up a reasonable amount of room on the old iTunes takes up too much room on Catalina apps. That's the nearest I can figure. Stay tuned, everyone.

just needed to cry out my total frustration with the new podcast app that came with Catalina. It is syncing my iPod 8g like crap. Please Apple, just restore iTunes... This is definitely the worst experience I have made with Apple upgrades in 10 years :/

I have exactly that problem! May have to do with not having external (with iTunes library) connected during switch to Catalina. In any event, I left the external unplugged and repopulated the new Podcasts app with what I wanted. BUT the synch window shows only old podcast shows, and only episodes up to the day I changed over to Catalina. Been working on this for a week now. I can't figure out where the sync window is pulling from.

However, I just found that even after updating/refreshing my podcasts in the Podcast app - the finder will not recognize new podcast episodes.

How lame!!!