iPod Classic sync with macOS Catalina???

I've tried with all my iPods ( nano, shuffle, classic, video 5.5 ), for all the result is the same...eternally stuck on connecting. I've always restored on other machine ( windows, other mac with older OS ), perfect working on that but always stuck on catalina...what a disaster by Apple...I hope they will fix it soon because it's a serious problem for me and I can't revert to mojave...

Just to expand on whalecanes answer - if you cannot get your ipod to stay in the finder (stuck on connecting but not displaying anything), find another computer with iTunes, and then reformat there.

I reformatted on my media center PC (Windows 10), and then connected to Catalina. Then reformatted for Mac (it did not ask, but I figured just in case), and its now syncing.

Now I think the only problem is finding the setting in the Catalina app store to download a lower version of the standard definition.

OK, so I can connect and sync my iPods (Nano 7th Generation and 4th Generation) to a MacBook Air running Catalina, but not to an iMac running Catalina. This means I could sync using the 'Air' - that's the good news. As I wanted to sync on the iMac I restored both on the 'Air' and then had another go at connecting them to my iMac. No change - just tells me 'Loading' and that's where it stops. Seems to be machine-specific for me which I can't understand. I even tried re-installing Catalina on the iMac from Recovery Mode. No change. Apple are really frustrating at times.

Chiming in to third this issue with an iMac.

Restored/disabled disk mode on my MacBook fine, won't pass the loading message once connected to iMac.

Pretty disappointed... I expect "minor issues" with updates like these, but seriously, you have alphas and betas to smooth these issues out.

Some wise words for you Apple, "Never half-a s s two things, whole-a s s one thing" - Ron Swanson.

I would like to know the braintrust who decided to fix something that was not a problem or broken. I liked all my iTunes media (music, podcasts, movies, tv) in one place not broken into pieces. If I have to do this every time I need to get new music and podcasts on my iPod Classic I will seriously think about getting a new pod catcher app.

So after going round in circles with this for the best part of an hour my iPod classic is now syncing. I have no idea what solved it. But here are some of the things I did.

With the iPod disconnected, restart the macbook (i've an oldish macbook pro i7 processor)

Log in to the mac

Hard restart the iPod (hold menu and ok button for over 8 seconds)

Plug the iPod into the mac

Open finder and click the icon of the iPod - this then gave the option of syncing.

Immediately before this I had a message in music that I needed to use finder to start using the iPod

So I went to finder, and there was a notification to start using the iPod, but everything just froze (which is when I did the above)

Before this, I went through blowing on the usb connections, restarting the mac (lots of times)

I was lucky that when I first plugged the iPod in, it asked me if I wanted to restore the iPod.

Hopefully it will continue to sync.

Well something happened during the times I tried to sync and not for the better. I tried playing music on my iPod, but wrong album cover art has been replaced and the songs are there (info is displayed) but the track/s do not play! It seems as though the audio itself is missing?! WTF

That is 60GB of missing audio from my iPhone!!!

Someone needs to FIX THIS NOW!

I am using a MacBook Pro, but will try doing what koko above suggested. Can’t get any worse than what has happened … FFS

I did this and it solved the issue...!...... Only temporarily. I restored it and reload it and it synched fine the next time. However, the next day it was back to square one. The ipod says it's connected and synching but nothing happens, it never stops synching no matter how long I leave it connected, and it doesn't update the "recently played" playlist so it's like no info is transferred to the iMac. What a drag...

Unfortunately, this keeps happening. The lifecycle is more or less like this:

I connect the iPod Classic. It gets detected and starts synching... and never finishes, no matter how many hours it stays there, it syncs forever without finishing. I can "force eject" it and plug it again but the same keeps happening. Eventually, I restore it and sync the music again, which of course takes hours. Then it works fine, I can sync without issue, go listen to music to it, sync again and it will sync my recently played playlist with the iMac fine, and any changes in playlists will get synched....

....This however only lasts around 24 hours. Eventually, one time I plug it again it will start sync and never finishes, and it will stay that way until I restore it again. Then it will start working again for a while until it enters the synch of terror again.

This was perfectly functioning iPod Classic that never had any issue until I upgraded to Catalina. Wish I never had.

I also second that link. I had an apple authorized tech specialist replace my ipod classic hard drive (the original one it came with) earlier this year with a solid state. Also, when I did the restore on my windows it fixed an issue on it related to something else, and no issues have reappeared on my ipod classic since the first initial attempts.

Screw this. I’ve reinstalled Catalina only to find it is still broken and not working as it SHOULD HAVE in the first place.

So, I am reverting back to Mojave when everything worked.

Since Jobs has left us, Apple has continually declined and the old moniker “it just works” was buried with him.

Pathetic.

Hey boomer the issue isn't the iPod, it's the Mac OS.

Constantly posting your guide isn't going to fix the fact that iPods are unable to sync with iMac platforms, even after the latest update.

What I would say old man is humor us iPod + iMac users and confirm if you experience the same issues on an iMac as we do. Feel free to record it and post it on YouTube if you are able to get things working.

Otherwise I guess we will continue to twiddle our thumbs and wait with our iPod bricks until Apple decides to remedy the issue.

Christ I hope SOMEONE from Apple is aware of this.

Ah, the irony. After initial problems with my classic which I restored and then got working with Catalina I accidentally synced it yesterday with a test library that contained a solitary song. Having switch back to the main library I set it syncing again, intending to show you a screenshot of the fully loaded device. Instead I work to discover that one of the tracks hadn't synced. Not so bad I thought, I'll just try again. No response to syncing. OK, eject and reconnect I think. At the last moment it resets itself and then announces there are no songs. I check the stats. One pending sector. Reconnect to Catalina. Device needs to be restore. Then restore it say I.... Nothing happens. OK, once more with feeling. Nope. OK, disconnect, reconnect. I now have a mostly empty white screen that says Software: Loading...

Clearly this isn't going well for me either.

tt2

Is anyone seeing their playlists in the sidebar when their Classic is plugged in? I can see the contents of my iPod, but that's literally all I can see. None of the playlists I've assembled over the years appear to be accessible in any form.