iPod Classic sync with macOS Catalina???

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.

I found an easy solution that works for my iPod Classic and MacBookPro.

-Connect the iPod to the Mac

-Open the Music App on the Mac

-The iPod should show up on the left - select it

-On the upper right of the iPod screen is a button Sync Settings - select that

-On the lower right is the Sync button - select that

A finder window will open with iPod showing on left, with the spinning wheel indicating that is is syncing. Unlike when starting from a finder window this one actually works and finishes fairly quickly

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.

Have you tried a SMC reset? One of the reasons to perform a SMC reset is for USB connected devices that are not recognized. Instructions for a SMC reset differ depending on the type of Mac - search for "How to reset the System Management Controller (SMC) on your Mac". I assume you've already tried a different cable, and using a different USB port on the Mac (directly, not with a USB hub). Mine works with a hub, but I have an older laptop that still uses USB cables with the B-type and A-type connectors at opposite ends (not the newer USB C-type connector).

I'm using macOS 10.15.2 (19C57) with Kernel 19.2.0. I have a 160 GB Classic (6th gen.) that was first sold in 2009, and discontinued by Apple in 2014; Apple stopped selling Classics around 9.Sept.2014. Also a 80 GB Classic (5th gen.) that was first sold in 2006. The 6th gen. unit still has all original parts. The 5th gen. unit was repaired by a third party (micro disk and battery replaced). Both are formatted for Mac (not FAT-32 for Windows).

Forget macOS Catalina for good if it comes to syncing pre-iOS iPods. Apple is truly a drag. Since 1982 I am an Apple customer and I bought a helluva range of products. Now they cheated badly. How can I classify devices obsolete when they were sold until 2014?

I only have the following advice which hopefully solves things at this point: get a copy of Parallels Desktop software, install macOS Mojave in a virtual machine - and it syncing works the old way by using iTunes running Mojave.

I can only hope that Apple will shed their ignorance and update Catalina to enable syncing our beloved old iPods. Steve Jobs would kick the guys badly who ignored the old iPods.

Make sure that you are using the original Apple iPod cable, which should be Apple brand. That did the trick to me.

That said, in my opinion Apple is the most abusive, customer-bleeding, ominous, arrogant company that has ever existed, and it only deserves to go broke. They can make you waste weeks of your life, get your blood pressure to the stratosphere, only to force you to buy a freaking little cable.

Restored the iPod on my MacBook, which also runs Catalina and no problem recognising the iPod in the finder sidebar, and hit restore. Then plugged it into my iMac and it appeared in the finder. Took me a few hours to put all the songs back though. Waste of time but, but it solved the problem. C'mon Apple fix this problem!

Too complicated. My advise is: Try using the original iPod white Apple cable. That simple trick did it for me. I hope this helps.

Yes and no. In my case, a restore will successfully sync my iPod Classic (and it takes about 12hrs, since I replaced the Classic's hard drive with 400GB of micro SD cards). However, every subsequent attempt to sync fails again. So it's like a one-time refresh that's a one-way street from the computer to the iPod. Very frustrating, since all of the work I've put in to rate songs on the iPod gets lost every time I have to do this. Apple -- please, please fix Catalina's sync issues. Related: once in a while, I can't shut down in Catalina unless I go to Activity Monitor and kill all of the processes that begin with AMP: AMPArtWorkAgent, AMPDeviceDiscoveryAgent, AMPDevicesAgent, and AMPLibraryAgent -- essentially, all of the software that runs device sync with my library. So it seems pretty likely to me that the fundamental toolkit that handles device connections to Catalina is a buggy mess.

Check the devices in Disk Utility with First Aid. You may need to reformat to Mac on another system if Catalina won't play ball.

tt2

I wonder if you’ve misunderstood. We’re talking about syncing older iPod classics with scroll wheels not touch screens. These will no longer sync with Catalina OS. With no sync there’s no restore and without restoring there’s no sync. Apple’s plan to phase out legacy devices. Bad bad move.

This is nothing new. I started working in IT in 1978, and have seen this over the years with various peripherals using various cables (parallel, USB and SCSI). I've seen it with my SanDisk mp3 player most recently. There are charging cables and syncing cables (which are more expensive). Best to verify that the cable has ALL needed pins connected to wires in the cable (some only have the most frequently used pins connected). Back in the day, some of the connectors had 30-50 or more pins, but some applications would require maybe 4-12 pins be wired. Some manufacturers save money by using less wires within the cable. There were also applications where certain pins had to be wired to different pins at the other end of the cable (called a cross-over cable); the other type is called straight-thru.

Yes. Syncing legacy devices w Catalina is now impossible. It’s Apple’s corporate decision to phase out all older devices. Terrible move and very alienating to loyal long-time customers like me who owns several Classics, Shuffles etc.

So suddenly my iPod is now synching. It took about five restores before it began working, and sometimes it doesn’t appear to be working at first — but a few minutes after the little synch spinner in the finder window sidebar has been moving, the iPod switches from “eject before disconnecting” to “synching.” The only thing I did on the computer was switch off a network waking option. I would not think the two things are at all related.

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.