iPod Classic sync with macOS Catalina???

I suspect it will be a little more complicated than that. See Corrupt iPod Classic - Apple Community. What are your HDD stats? If there are any pending sectors then you could be seeing a knock on effect from problems reading part of the hard drive.

tt2

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 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.

Ok, I think I have figured out how to deal with Audible Books.

1. Open iTunes.
2. Under Sync Settings/General check "Enable Disk Use."
3. Open Books (not sure if this is necessary but I had it open when it worked for me.
4. In iTunes, under Sync Settings/Audiobooks check "Sync Audiobooks" and "All audiobooks" (more on that in a minute)
5. Sync the iPod Classic

I tried various combinations of settings, but nothing worked except for this. When I went to use my iPod, the books appeared and seemed to be playing fine under "Audiobooks."

Now, I hope this method works for you. I am going to suggest that if you want to remove an audiobook, you need to take it out of Books before you re-sync. For those of you who have a lot of audiobooks, you're not going to want to keep them on your hard drive. Since the majority of my audiobooks are Audible, my Audible account is my backup. If Amazon goes out of business, well, that's life. The alternative is a separate drive.

I have no idea what it does with Podcasts as I listen to them on my phone. But I use my iPod almost exclusively for listening to Audible books and hopefully this is a solution that will continue to work.

Ok went and did that:

Retracts: 53

Reallocs: 1088

Pending Sectors: 0

Power On Hours: 804

Start/Stops: 73072

Temp: Current 28

Min 4

Max 57

Anyway, what I've been doing now is that I'm only synching 2 o 3 playlists, so when it starts having problems synching, I restore and sync only those playlists and it finishes fairly quickly. Of course is annoying because I don't have all my library with me but is that or nothing....

A funny issue now, the playlists I do synch are not in order. I have the playslits sorted by Artist in the Music App, but the iPod sorts them randomly. I've tried sorting the songs by different criteria in the Music App and synch again but no matter, the iPod sorts them in the playlist by its own criteria which I can't figure out what is. Goes without saying that this didn't happened once in the previous 10 years with the classic, until Catalina arrived.

All this is very frustrating =(

Well after installing the latest “update”, I can report that it is nothing but a waste of time. Nothing to do with the iPod problems was addressed.

I’m STILL getting the “device is not recognised” alert and STILL have to Force Eject the iPod from my MacBook Pro.

so … screw this sh*t. I’m outta here and reverting back to Mojave.

Thanx for nothing Apple, ya bunch of arse clowns!

Frustrating here too. I'm waiting on my classic to reload after it all went haywire yesterday and Catalina was unable to restore the device. I my case there was a pending which cleared properly after a restore in High Sierra, but reloading in Catalina is a real drag with no progress indicator.

tt2

My earlier post with the fix for audio books - it worked, but I may have lost the chapter markings in the audible books. I’ll have to do a bit more tinkering after work tonight, but I’m about ready to ditch the iPod and get a Sandisk MP3 player that I know will work with them. I have my music on my phone.

v. Similar here: 160gb iPod plugged in permanently and used as a jukebox. All 120gb of music is there but iTunes won’t let me do anything with it: no playing or editing or get info or whatever! Very, very annoying.

Hi All, Like everyone, I've been struggling with my iPod Gen 5 (Model #MA0002LL), and finally got it to work:

• Connected it to my Mac Mini
• In the Finder's iPod screen, I selected Restore.
• I had to do this about three times before it worked. The first time it said the update software was busy. Another time the iPod never came back until I disconnected the USB. The 3rd time the Finder came back after a few minutes with "Time to Setup your iPod"
• In the General screen, I selected "Manually Manage Music, etc." and "Enable Disk Use"
• Now this is key: I selected a playlist that had every song downloaded to my hard drive.
• Until now, all my music was in the cloud, and only one song would sync. When I downloaded all the music in the selected playlist, using iTunes, all 33 songs sync'ed as planned.
• Wonderful right? Except that, like everyone, I have a bazillion songs, and can't/won't download them all.
• But at least it made my beloved iPod useful again. Now I have to decide which songs to download.

Hope this helps. Let me know if it works for you too.

Joe

I'm using a 2017 iMac running Catalina (10.15.1) and then, as suggested, erased my iPods (circa 2006 & 2009). The update software was 1.3 and 2.0.5. After erasing them, I ejected them and then hooked them up to sync. It worked just fine. I was able to update and see my iPod in a Finder window as opposed to the newer Music application which replaced iTunes. But my music library is still all within Music. You may need to navigate the menu options once you see your iPod. I had to check "sync with all music." Maybe that's the problem? All of the settings when you sync by default will likely be manual.

I'm officially done with Catalina.

I can in fact get my iPod classic to work under Catalina, I just no longer want to. There have been a number of issues that have failed to be resolved since the release of Catalina, most of which I could live with. I can live my iPod Classic not stopping at the end of a podcast and just moving on to the next. I can--mostly--live with the fact that it doesn't remember where I stopped in a podcast if I sync or switch to a different podcast without having completed the podcast. I can even live with the loss of chapters in my audiobooks, and the ability to download audiobooks longer than about 10 and a half hours as a single file.

What I really just can't live with anymore is the inability to manually manage my podcasts. It's irritating to me that I can't import a file as a podcast into the podcasts app. Apple's always been a bit on the authoritarian side with respect to what they do and do not let on computers, and I suppose this makes sense from a software perspective. It makes no sense from a podcast perspective. Apple will TELL me what is and what isn't a podcast, and if I can't download it from them, too bad for me.

That's it for me. I'm backing up with a Time Machine backup of my last day with Mojave.

Good bye, Catalina, and good riddance.

Lessons learned from Catalina 10.15.2 sans iTunes:

1. As with most prior updates, syncing check boxes and radio buttons had to be changed after the update (but this time in the Music, Podcasts... tabs that pop up in Finder when you click on the first (of sometimes two) iPod devices under Locations.
2. MP3's downloaded from sources other than the Apple Store need to be copied into the Music application. Had to use "file" from the menu bar, then add to library (or short-cut command O), then navigate to location, select the MP3's, and press the open button. Dragging and dropping files did NOT work (sync could not find files) - only allows you to play in Music. Looks like the "Automatically Add to iTunes" automation either did not convert with with update, or does not work.

After these changes/actions, a circa 2008 80 GB iPod Classic and a circa 2013 160 GB iPod Classic successfully synced. A YouTube video that is floating around indicates success with an 18 year old original iPod Classic. Suspect some of my initial issues may have been due to particular setup of my former "Automatically Add to iTunes" folder, since, after running Catalina update, it contained new entries for "Automatically Add to Music" and several other entries. Maybe I just needed to change the download location in Safari. For now, just downloading MP3's to downloads, and selecting them from recents.

Did notice that Time Machine and several other items appear to run faster under Catalina. Java control panel appears to take longer to open.

Saw the videos, and thank you for the referrals. But in neither did I see any reference to iMacs. I have read several posts that talk about success syncing iPod Classics while running Catalina on a MacBook, but no one using an iMac. I'll probably stay with Mojave until I get some real concrete evidence of success with this issue on iMacs.