iPod Classic sync with macOS Catalina???

Try this: https://support.apple.com/en-us/HT204688

If your iPod turns on but gets stuck during startup

If your iPod still won't respond, gets stuck during startup, or persistently displays an Apple logo or , here's what to do:

1. Make sure that your computer has the latest version of iTunes.
2. If you have an iPod nano or iPod classic, put your iPod in Disk Mode.
3. Open iTunes, then connect your iPod directly to your computer.
4. Find your iPod in iTunes, then select Restore.

Worked for me with an iPod Classic stucked on Apple logo.

I used the disk mode and finally got recognized by the Mac ( I also have Catalina). It has been resetted and is restoring the music.

iPOD CLASSIC and CATALINA Finally Getting ON TOGETHER

All Working and Syncing Perfectly after doing a DFU Restore on all of my Classic iPods 160GB.

I was helped enormously by one of the top Level Contributors. He has a entire page on how to Restore your iPod.

Mine did not SYNC at all and I had the same problems however after a few different tries at Fixes the DFU was the one that worked for me.

I am adding the page link here as it MAY JUST HELP someone.

https://discussions.apple.com/docs/DOC-10101

turingtest2

User level: Level 10 (195,378 points)

Apple Music Speciality level out of ten: 10

I have included photos of my Sync Session today to clarify that it is all working with macOS Catalina Version 10.15.3

Software Version on the iPods is Up To Date : 2.0.5

I Choose to Sync all of the iTunes Music I have just to check it all out. This shows the iPod at the start with Space Available

And here is the iPod with All of my Music stored in the old "iTunes" App and now in "Music" App.

I was having the EXACT SAME PROBLEMS with No Syncing but restoring each iPod made this possible.

Your iPod classic should show up in Finder. See What happened to iTunes? - Apple Support. Syncing and other device management duties have been delegated to Finder in macOS Catalina. If it won't appear try rebooting the device, try placing it in disk mode, or try another known good cable. In some cases it might be necessary to restore the iPod on another machine if your just won't pick it up.

tt2

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

Humour an old man. See Corrupt iPod Classic - Apple Community. What are your HDD stats? I'm happy to believe that Catalina's support for iPods isn't perfect, but there is also a chance that working with the new OS has uncovered data rot you were previously unaware of.

tt2

I would echo the view that Catalina doesn't seem to like Windows (FAT32) formatted iPods. If you cannot get Catalina to restore the iPod take a look at Corrupt iPod Classic - Apple Community. What are your HDD stats? Note that if macOS thinks a connected drive might be corrupt it can sometimes invoke disk first aid in the background, which can prevent foreground access to the device while it is being inspected or repaired.

tt2

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.

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.

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

Mine are mostly syncing fine at this point. Sometimes it syncs, but never appears as an iPod in finder, just a generic disc.

I do not manually sync songs, I’m syncing entire music library, selected podcasts, and selected audiobooks. Disk mode is not enabled.

While all of this might sound encouraging, problems, I’m still experiencing include:

1. Loss of last listened time location in podcasts.
2. Failure to stop playing at the end of the podcast, despite being set to do so.
3. Loss of chapters in audiobooks.
4. Failure to recognize podcasts as played unless the iPod is synced immediately after finishing. If I move on to another podcast, the one I’ve listened to shows up as unlistened after syncing.

The annoying thing about Apple’s response that they ‘don’t support legacy products’ like the Classic, is that I don’t need them to support it. I’m happy with it as it was, I just ask that you don’t mess it up.

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.

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.

Sounds like a good plan.

A few more observations and discoveries:

1. With sync set to automatic, when iPod is connected: I think this should read when ipod is connected, AND you open the iPod in Locations within Finder. Unsure if this implies you could sync multiple/many devices at the same time (not going to try a concurrent sync to two iPod classics - not important to me).
2. Have been using a cleaner (CCleaner) for 12 years (about 6 on Win, followed by 6 on Mac). Ran analysis of Music and Podcasts on CCleaner, with supposedly nothing in the library and nothing showing on iPod. Oddly, it showed 8 files eligible for deletion in Podcasts, and more than 500 in Music. Ran the cleaner against these. Then added some music (spoken word copied from a web site) to the library, synced to iPod Classic. The iPod worked fine in Music. Reran analysis, which now showed 8 files (4 spoken word, plus 4 cover art?). Did not purge anything this second time, since results seemed reasonable. Will test Podcasts when the only Podcast I listen to resumes next week. Wonder if there were multiple versions of the iTunes library on pre-Catalina Mac, and maybe some problems internally? Also found more than 150 MB in caches, although I'd cleared several caches manually before analysis (about 65 MB returned shortly after clearing the 150 MB).
3. Bit of a learning/adaption curve, but small compared to what I've seen in the past, going from paper-tape teletype input, punched cards and toggling a program into a computer from the control panel, then to various green screen text interfaces, finally to various GUIs on various devices. I'm sure full voice and augmented reality will be another leap.

Refinement of observations, after several weeks of successful use with Classic iPod:

1. ALWAYS close Music and Podcasts applications on the Mac before attaching older iPods to the Mac. Looks like Finder (which does syncing with pre-iOS iPods) may have file or other conflicts with Music and/or Podcasts applications for syncing pre-iOS iPods. For older iPods, do not change sync settings in these applications (only change in Finder); looks like changing older iPod settings in these apps may cause locks/problems.
2. You cannot sync the older iPods from the cloud. For Podcasts, looks like you must add the podcast to your (cloud) library, then download the podcast. (Did not test the subscribe to podcast route.) For Music, if you download or create MP3s, you must add these to the (local) library using command O.
3. Once you are ready to sync the legacy iPod from the Mac, close the Music and Podcast applications, attach the iPod to the Mac using a USB cable, open Finder, scroll down to Locations, and TAP on the first (of sometimes two) iPods shown in the list (not the eject button on the list). A screen should appear to the right of the Finder list that looks like the old sync screen in iTunes. There should be a sometimes brief display of arrows spinning on the list entry you just tapped (this display appears over the eject button). For me, if I wait about 45 seconds, the sync arrows then appear on the iPod for a short time (remember, the older iPods have relatively slow CPUs). When the arrows stop spinning on the iPod, press the eject button on the entry in the finder list.
4. If problem persists, verify you've selected "automatically sync when iPod is connected" and "enable disk use" under the general tab of the iPod in Finder. Verify under the Music tab that you've selected "sync music onto iPod" and "entire music library". When I selected "sync music onto iPod", there was an inaccurate error message that said I would replace the contents on the Mac with those on the iPod (should have indicated that I would replace the contents of the iPod with those on the Mac).
5. An oddity I've seen is that the Podcasts I download from the Podcast application appear under both Music and Podcasts on the iPod. Formerly, these appeared only under Podcasts on the iPod. Hope this is rectified in the next update, but I can live with that for the present.