iPod Classic sync with macOS Catalina???

I'm going to chime in here with my experience, even though I've not been active in this forum since I downgraded to Mojave. t

Before I downgraded, I could get all of my iPod Classics to sync with Catalina. I can't speak to anything beyond the 10.15.2 version though. I didn't downgrade because I couldn't sync, I downgraded because the behavior of my iPod was unacceptable. I've outlined those issues elsewhere in this same thread, I believe. The issues included, but were not necessarily limited to:

Failure to remember location of partially listened podcasts

Failure to stop playing at the end of a podcast, despite being set up as such

Loss of chapters in my audiobooks

I'm perfectly content with Mojave. Someday, I may install Catalina on a second partition and occasionally try to sync from there; however, I have ZERO confidence that Apple has any interest in supporting such legacy devices.

But how do I wipe it if I can't connect it to the mac???? :(

I don't have any restore button in my windows while I've connected my iPod....stuck on connecting and nothing more....

Same here. Ridiculous that they release the new OS when it’s so full of bugs. Apple has really hit the skull in recent years!

This is no longer an option.

iTunes doesn't exist in Catalina.

Either way, my audiobooks just disappeared from my iPod classic AGAIN!

Like I said previously, revert back to Mojave and all your problems are solved.

The problem is Catalina will not allow music to be managed on iPod classics. No way around that yet. Sucks!

That support article is from 2017. iTunes is no longer present in Catalina.

ipod stalls at loading. no option to sync in music app or finder. if yours is working/syncing then you are not using os catalina, or not using an older ipod classic, shuffle etc.

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.

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.

My classic works intermittently. It always syncs but sometimes only appears as a generic hard drive. The problems I'm having are:

1. iPod stores only new podcasts. It doesn't remember positions. If I listen to half a podcast and sync, the podcast is still there, but stores as not having been listened to.
2. The iPod plays continuously no matter what the setting is in Podcasts app. I have it set to stop after playing, and the iPod just keeps right on going.
3. My audiobooks keep automatically unsyncing themselves. I've had to go through the rigamarole of deauthorizing both my computer and audible accounts on a daily basis.

Super irritating. I'm thinking about downgrading to Mojave.

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