iPod Classic sync with macOS Catalina???

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.

I use my 80gb Classic for night time tinnitus relief. Unfortunately developed an “error” last week, so I decided to connect to my MacBook Pro running Catalina and do a synch.. Big Mistake! It first of all didn’t recognise it, then eventually said it was corrupt and needs restoring, which I did.. then it errored out. So now I have a brick. Disc errors on the iPod are in low numbers but I can’t get the o/s back on it. I shall try reformatting the disc on my iMac 2009 with High Sierra later. So annoying!

Agree. I've been speaking to Apple Support / Technical Support and got nowhere so it's now with Apple Executive Relations. When I say 'it's' I mean the abysmal way Apple deal with a loyal customer base. Every time I speak to someone they have no idea why they're calling me and I have to repeat the story. I've wasted getting on for 4 hours on the phone / Chat getting nowhere (but getting really frustrated). My advice is don't follow my example and foolishly believe that Apple are interested in dealing with us in an efficient way.

I have iPod 5th gen. I see the iPod on the finder window sidebar, but can't find "restore" anywhere in finder... All that's listed in the file section are 3 folders... Calendars, Contacts, and Notes. Please help here!

Don’t know if anyone else has noticed, but ever since the abomination known as the Catalina OS, there has been a sh*t load of iPod’s put up for sale on FB sites and eBay. Seems that owners have given up and started offloading their “bricks” …

Several days ago, I successfully reloaded my iPod Classic after I first installed Catalina on my MacBook Pro. But now, several days later, when I tried to update and sync again, this happened repeatedly: I plugged the iPod into the Mac, the Finder window sidebar recognized the iPod (under "Locations" and with the "Eject" delta to the right), and the iPod screen showed "Synchronizing" and the two arrows spinning slowly in the screen's yellow-orange circle. So far, so good. The Finder window continued to recognize the iPod, and clicking on the Finder window iPod link yielded the expected and appropriate boxes and screens, incl. "Music," so I checked the "Sync Music onto...iPod" box, checked the "Sync: entire music library" box below it, and finally clicked on the "Sync" button at the bottom right, which then went gray and stayed gray. The iPod screen continued to show "Synchronizing" (as above), but the Finder sidebar still had the iPod listed under "Locations" with only the original "Eject" delta and no spinning arrows that usually signify syncing. So: Was it syncing? If it was syncing, how would I have known when it was done? If it wasn't syncing, what should I do? I am concerned that "Restore" might very well "clean" the iPod but that reloading it, given this glitch, might not happen successfully and I would lose my iPod's entire (and substantal) library. One final note: after a while, I went back to the Finder window iPod link and, after clicking on it, the "Loading" page came up, and many, many, many minutes later, remained up with no sign of the "Music" or of any other box or page. I finally gave up and used "Force Eject." The good news is that the iPod tracklist remained intact as it had been after the initial reloading days ago, but no further updating took place. Any help anyone can provide would be greatly appreciated. Thanks.

Just to jump in, I have an iPod Classic and tried to sync it with Catalina. Lost everything.tried 3x to get everything back. First 2 times it restarted at about 30g. Last time it went all the way to 155g and wiped itself. very disappointed. Realized there is a newer update to Catalina. Will try again tonight.

Disappointing.

I wonder if the differences people are experiencing could be related to the file format. All of my iPods are MacPods, that is they are NOT formatted FAT32. Is it possible this formatting prevents syncing?

Just kind of scratching my head and trying to understand the completely different things people are experiencing

So formatting is probably not an issue for me. I reformatted today and has been using the same Mac for five or six years.

I am really annoyed by the solution of using only manual song selection. I have been using select by checking the boxes for ever.

Wow! I can’t believe this screwup hasn’t been fixed yet. Even though I gave up and just rolled back to Mojave and a working OS with my iPod Classic, that just isn’t the point. Apple is an embarrassment and a pale shade today of what it once was. It’s quite obvious that this problem is not a priority and I highly doubt it will be fixed. For those who have lost their library and did not have a backup, I feel for you. My music is everything to me and I would be absolutely gutted. I suggest everyone, if they haven’t already, bomb Apple with multiple emails expressing their disgust with how loyal customers have been treated.

I for one will not be buying any new Apple products in the future. I see no need. They don’t and haven’t had anything new or exciting for years now. Other manufacturers are way ahead of the game now.

Good luck all …

I’m pretty sure this is the problem. New iOS doesn’t support fat32 does it? This could explain why my classic powers up but the drive does not spin.

either way, I’m in a better position now after a two day library rebuild / iCloud upload on a windows pc as recommended by a dude(ette) on here.

when I’ve time, I’m going to attempt a wipe and restore via the iMac to see if it can be used again.

Well, just to add to the frustration: Now that I've got my iPod syncing and not dumping my audiobooks, in addition to the fact that chapters are gone, apparently, long books aren't "supported." For example, I have a 20 hour book that I'm reading now, and it quits after around 13.5 hours. Now, I'm trying to download the books in parts and see if that resolves the issue.

Thumbs up, Apple!

Thank you! will retry, I did as you mentioned but the iPod stays at syncing until it times out. Don't know if it has to do with MacBook since I'm using late 2015 or iPod generation, since mine is running 2.0.4. and mentions it's the latest... I will retry using a PC to see if this changes the result.

General update: 20 Nov

Just attached my iPod Classic 80gb up to Catalina on MacBook Pro after three weeks of miserable failure and it has restored and is synching as it normally did. 🤔

Looks like someone at Apple has been listening.

My settings are syncing music automatically, entire library, all playlists, etc. I sync selected audiobooks, and I sync selected podcasts. I do not manage music manually, nor do I enable disk mode.

For the most part, my iPods are functioning in a usable manner. Difficulties, I'm still experiencing include:

1. Failure to remember my location in podcasts that I've listened to partially. If I stop listening to a podcast, and navigate a menu back, when I come back to that podcast, it starts over again, even though it's not 'bluedotted' as new.
2. Lack of chapters in my audiobooks. This is super annoying to me. I don't need Apple to support my legacy devices, I just don't want them to mess them up.
3. Failure to adhere to my settings; I've set my podcasts to stop at the end of any given podcast, but they don't, and keep breezing through the list. This wouldn't be so bad if one of my other settings wasn't being ignored, specifically, that I'd like my Podcasts to be arranged oldest to newest, but this is apparently an impossibility.
4. Inability to download audiobooks longer than a certain length as a single file. This wouldn't bother me if it had always been the case, but I suspect it has something to do with the loss of chapters. After about 13 hrs, if an audiobook is downloaded as a single file, the book will just stop. If you try to force the start point past that, you get 2 secs of gibberish, and then the book restarts. Audible claims that the iPod Classic is limited in terms of file size, but I downloaded, for example, Man, Economy, and State, which is like 57 hrs long, as a single file and listened to it without difficulty prior to Catalina. Now it looks like I'll be re-downloading all of my long audiobooks as multiple files.