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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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185 replies

Jan 16, 2020 2:05 PM in response to danielfrombolingbrook

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.

Jan 16, 2020 2:16 PM in response to WReist

Thanks for posting all that. I just recently received a new 128GB iPod Classic with an SSD drive. I'm still in Mojave, in which the iPod Classic loads just like my iPod Nano has—in the browser window at the left in iTunes—and syncs beautifully. In reading your post, with the convoluted procedure to work with classic iPods in Catalina, I think I'll wait to see if Apple comes up with a new update in Catalina that deals with these devices in a more seamless way. I may even try to wait for the next major system if Catalina has no further updates.

Jan 18, 2020 12:49 PM in response to WReist

Thanks for the tips. None of them helped me. I followed all your instructions (to the extent that I could) and none of my five iPod Classics get past a spinning gear in the finder window before eventually defaulting to message - "The selected device could not be found". So, can't even get to any of the sync/apply music functions... or anything else for that matter. Been trying for several weeks now. Sad,

Jan 19, 2020 4:05 AM in response to kulufmsmon

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).

Jan 19, 2020 6:49 AM in response to WReist

All of my Classics (including my 120 gb) show up in the Finder sidebar list. When I click on the first listed iPod the main window says "Loading" with a small spinning gear. It also gives me the name and info of the iPod on the top banner. Then after 5-10 minutes the Cannot Locate Device message replaces the Loading messag. Frustrating.

Feb 3, 2020 10:24 AM in response to whalecanes

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


Feb 3, 2020 4:43 PM in response to DISCO1979

No good. My iPod stalls at Loading... after a while a message that the selected device could not be found& won’t allow to use the Sync Settings in ITunes or Finder.


Hope Apple fixes this or I’m not buying anything else from them after being a loyal customer for 15 years: 4 MacBooks, tons of iPhones, 4 iPads, +6 iPods, etc etc.


this lack of care and communications really frustrates and disappoints me.

Feb 15, 2020 5:07 AM in response to whalecanes

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.

iPod Classic sync with macOS Catalina???

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