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iPod Classic sync with macOS Catalina???

Side bar is recognizing my iPod classic but the second its connected it says its syncing but nothing is happening, just spinning. Left on even over night and still the same. I even selected some playlists to add and the apply button still is grey'd out. I have to force quit it to eject the iPod. Any help???

Posted on Oct 8, 2019 9:21 AM

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Oct 9, 2019 5:56 AM in response to rainpaint81

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

Oct 9, 2019 7:59 AM in response to whalecanes

Mine was connecting just fine in the Sidebar. Even if the sync arrows were already spinning I still hit the restore button. The screen of it looks the same as in previous iTunes screens. I just waited a few minutes then it asked me to restore the iPod and I clicked yes. That was it. I did it to my 2 iPod classics I have last night and everything loaded up great. Though some artwork was missing which I'm seeing is a bug in the system but can easily be replaced.

Oct 10, 2019 1:26 AM in response to Ramblin' Pony

I've tried with all my iPods ( nano, shuffle, classic, video 5.5 ), for all the result is the same...eternally stuck on connecting. I've always restored on other machine ( windows, other mac with older OS ), perfect working on that but always stuck on catalina...what a disaster by Apple...I hope they will fix it soon because it's a serious problem for me and I can't revert to mojave...

Oct 10, 2019 3:42 PM in response to whalecanes

Just to expand on whalecanes answer - if you cannot get your ipod to stay in the finder (stuck on connecting but not displaying anything), find another computer with iTunes, and then reformat there.


I reformatted on my media center PC (Windows 10), and then connected to Catalina. Then reformatted for Mac (it did not ask, but I figured just in case), and its now syncing.


Now I think the only problem is finding the setting in the Catalina app store to download a lower version of the standard definition.

Oct 10, 2019 10:48 PM in response to whalecanes

OK, so I can connect and sync my iPods (Nano 7th Generation and 4th Generation) to a MacBook Air running Catalina, but not to an iMac running Catalina. This means I could sync using the 'Air' - that's the good news. As I wanted to sync on the iMac I restored both on the 'Air' and then had another go at connecting them to my iMac. No change - just tells me 'Loading' and that's where it stops. Seems to be machine-specific for me which I can't understand. I even tried re-installing Catalina on the iMac from Recovery Mode. No change. Apple are really frustrating at times.

Oct 11, 2019 9:14 AM in response to rainpaint81

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.

iPod Classic sync with macOS Catalina???

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