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Can't play music from my iPod Classic in the Music app on macOS Catalina

Before the update, as all we, I used to sync my iPod Classic and play music from it in iTunes, but yesterday I just updated to macOS Catalina and found the surprise that when I connected my iPod to the computer and tried to play a song from it, it just does nothing, nothing happens, also there's not right click to song, cannot sync playlists because it says it'll delete everything and so on, and I've been syncing my iPod with the same computer since Sierra, I mean, is the same Library, what happened? Did iPods just lost support with Catalina?

iPod Classic

Posted on Oct 8, 2019 8:18 AM

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Posted on Oct 8, 2019 2:17 PM

Well peeps I FIGURED IT OUT and unfortunately it's time consuming. YOU HAVE TO RESTORE THE IPOD CLASSIC!!! Yup wipe it clean and reload it all back. I have 20,000+ songs to do so that's why I mentioned time consuming but its syncing up nicely now. Just doing bits at a time.

38 replies

Oct 10, 2019 10:30 PM in response to turingtest2

thanks for your explanation tt2.

So established that with finder and music app is no possible to manage the ipod, how is possible to play songs on the ipod or playlists contents with the mac, now that itunes doesn't exists? Any of you has the same question? Does someone use an alternative application to manage and listen ipod music with a mac?

Oct 17, 2019 9:06 AM in response to Bobbyg13!

I always love coming to the forums for "help".


You get one of two answers, 99.9% of the time.


1.) Send us EVERY possible detail about your <insert device here> and every version via this tool/report/etc.

.... and rarely get any type of reply.


2.) Reformat and retry.


"Upgrading" to Catalina has a number of 'side effects', I strongly suggest NOT upgrading as the new rule-of-thumb from Apple is to always stay updated and always keep spending your cash on our new products.


/disappointed greatly in "Music" and this hidden 'upgrade' to my iPod functionality.

Oct 27, 2019 12:37 PM in response to whalecanes

Issues here as well. My iPod classic shows on the sidebar of the new Apple Music program, but does not show up in a finder window. I used to simply drag the recently downloaded music (album) icon from the iMusic window the the Classic in the sidebar to copy files. Now nothing happens when I try to do that. Catalina and Music are a drag in this respect. I hate that options are going away. Terrible!

I hope there is a fix in the offing.

Oct 31, 2019 11:46 AM in response to Dave2329

I have same problem with both my iPod Classic and newer iPod touch. The music library on the iPods show in Finder (not in Music), the playlists do not show, and I cannot play a song when I click on it. Was on the phone for HOURs with Support 10 days ago, they wrote up a ticket, came back the next Monday and took a video of my screen, and that was all I heard. Today is Thursday. They act like this is a problem unique to me, which it obviously is not.


The computer recognize the iPod, Finder displays the Library and that is all.

Nov 10, 2019 7:43 PM in response to holitaish

Same issue here. I cannot manage my music on my IPOD classic with the new MUSIC app in Catalina as I was able to do before with Itunes. I cannot play music from my Ipod through the new MUSIC APP neither. I have been manually managing the music on my IPOD classic for years, never sincing directly with a playlist or music library in ITUNES.

Just got off the phone with an apple tech that offered me different solutions.

1- try to go back to MOJAVE

2- try to restore my IPOD (and lose all existing music and playlist) that way I might be able to sync with new playlist created in music but not sure it will work

3- try to access and manage existing music on IPOD with ITUNES on another computer like a PC or other mac


I will try option 3 and maybe comeback with comments on that.


If any other users have update on that issue it would be nice to hear from you.


I was hoping that APPLE would just create a uptdate with music so that all the ITUNES features would still be functionnal with the new MUSIC app... doesn't seems it is going to happen... we probably are too few IPOD classic users in the world right now.



Nov 11, 2019 4:52 AM in response to Rick_Norm

Same issues with my classic, including with my new ipod touch. There are plenty of classics out there to justify making this problem go away. You are not unique.


After HOURS on the phone with Support, they wanted a video and said they would get back to me. That was two weeks ago. Senior support manager told me the reset solution is not acceptable.


Nov 13, 2019 10:09 AM in response to troutchaser54

You are so right. When I connected my iPod classic after downloading catalina not only was it not recognised but the system wiped completely my classic, 7,469 songs backing tracks etc., lost, no appology of course or a fix of how to retrieve my content from the Apple crowd I contacted through their online "live chat" after being constantly passed to and fro from one operator to another and had to explain the problem to each operator when I got to the fifth one I gave up as none of them had any idea of how to solve the problem. the last operator I spoke to told me that the iPod classic was old tech and I should buy an iPod touch to solve the problem, but at more than £200 I'm very reluctant to spend my hard earned cash to rectify the problem that is of Apples doing. Very disappointed at the attitude cause I though I was part of the Apple family!! well that's what they told me when I bought my iMac computer, my Apple iPad, and my Apple phone. guess I was ripped off!!!!!

Can't play music from my iPod Classic in the Music app on macOS Catalina

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