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Can't Manage Music with Catalina/Music App

I just upgraded my Macbook pro to Catalina, but I never would have done that if I realized there is no way to manually manage my music on my iPod classic. My computer recognizes my iPod, but does not give me the ability to manage playlists and songs. I do not want to sync. I want to manage manually. How can I do this with the new upgrade?

iPod Classic

Posted on Oct 14, 2019 1:41 PM

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Posted on Nov 5, 2019 12:17 PM

This is honestly a huge oversight by Apple and a major frustration as a daily user of an iPod classic. I did however find a clumsy yet effective workaround.


  1. In your Music App Library (formerly iTunes) Select the album or tracks you wish to add to your iPod and right click, then click "Add to Playlist -> New Playlist".
  2. Open the Playlist from the sidebar and select all of the tracks you wish to add.
  3. Right click on the selected tracks and click "Add to Device -> iPod"


Like is said this is a sloppy workaround but the only method I found to work. Inexplicably some albums give the option to add directly to my device when right clicking in the library, others only from a created playlist. All I know for sure is that I was able to add music to my iPod.


Hope this helps!

80 replies

Mar 11, 2020 4:43 PM in response to turingtest2

Doesn't work. The iPod shows up fine, but if I try and drag and drop MP3 files from my backup CD, it won't allow me to. If I first copy the files into Music, it still won't allow me to copy tunes on to the iPod Classic. I've tried using the Finder, but that's useless. I can delete individual songs by clicking on "Manage Music," but it's a nightmare because it only lists all the thousands of songs individually, not by artist or album. Plus, it doesn't allow for files to be transferred on to the iPod. Basically, right now I deeply regret moving to Catalina.

Mar 12, 2020 3:08 PM in response to Hwheeler

iPod Classic MC297LL

I had the same problem. Asked for Apple Support, it was unsuccessful. The only way to work around if was to go back to MacOS Mojave 10.14.6 and iTunes 12.9.5.5, the latest of the two, before the switch to Catalina and Music/Podcast/TV separation.

It's a pain, you will have to save everything on your computer externally, and then wipe your disk, reinstall MacOS from the factory setting of your Macbook, upgrade to Mojave, and then iTunes will be there working fine. I am not sure whether you have to restore your iPod, in my case I did cause I tried to restore it from Catalina.

I don't know if it is 100% black and white that iPod Classics and OS Catalina are NOT compatible, but for me they did not work together, so I back tracked back to Mojave and iTunes.

Keep your ALL your music and most important files one an external drive, manually manage your music, and your free to upgrade downgrade restore and all over again to fine the right combination that works for you.

RIP iTunes


Mar 12, 2020 3:53 PM in response to btormos

He'll forgive me for not name-checking him here, but someone posted this (below) elsewhere, and I tried it and it works!! It's still a pain having to remove tracks (Finder/iPod Classic/Manage Storage) individually, but I was able to add tracks to my iPod successfully:


How to add music from OSX Catalina to iPod Classic without iTunes.


1. Add new music to Apple’s “Music” app on Mac.

2. Close “Music” app.

3. Plug iPod into Mac.

4. Open two finder windows on Mac.

5. First window: Navigate to your music media library (possibly "iTunes Media"), specifically to the songs to be copied to iPod.

6. Second window: Open the iPod (the iPod icon, not the other one)

7. Second window: click [Manage Storage] button

8. Second window: click Songs in sidebar. You'll see the complete list of songs currently stored on the iPod.

9. Drag and drop music from window 1 to window 2. There is no indication that anything happened.

10. Second window: click [Done] button.

11. Either window: Eject iPod.

12. Check iPod contents for successful transfer.


Done

Mar 18, 2020 1:03 PM in response to oneshowatatime

oneshowatatime wrote:

I know that I have music on my iPod Shuffle because I just used it yesterday, but when I connect to my laptop and open it in Finder>iPod Shuffle>Manage, nothing shows up under Songs (or any other media types). It just shows on the storage bar that it's full of "Audio" (see 2 images below).

Should I Restore my iPod Shuffle (will that wipe it clean) so I can then try dragging songs to the device?


Probably. Yes, restoring will wipe it clean. Once restored it should be possible to drag and drop content from Music to the device in Finder, or set it up to sync with one or more playlists in Music. I'm afraid I haven't personally tested a shuffle with Catalina, but it ought to work.


tt2

Apr 24, 2020 7:34 AM in response to Jimbojazzprof

Manual management under Music/Finder in Catalina is a reduced experience compared to iTunes. You cannot play content on the connected device, nor manipulate playlists on it. New playlists can be created in Music and dragged over to the device, or you can create them directly on it. Keeping all of your media in Music and syncing the device with selected playlists is the way to go.


tt2

Jun 1, 2020 7:41 AM in response to jjw7899

@jjw7899, thank you for the post, I'm aware about drag & Drop, however when you are dealing with iPod touch it's whole different animal, it doesn't show up as an external drive in Finder as to other iPod, the only option is to Sync and to do that you will have to create a Playlist in Music then use manual Sync but the problem is it wipes existing music on the iPod touch, it's pain in the ***.

Jun 1, 2020 8:06 AM in response to Hwheeler

Exactly. I started this chain, and no one seemed to get it - you said it finally (again).


This was not a "glitch", this was a strategic decision. Apple is looking forward to new generation of Music users who will pay subscription fees. We will no longer own our music libraries, any more than musicians will own the the music they created.


We are also the same generation that thought of Apple as a different kind of company than it is now. We are not their future. We went with Steve Job.

Can't Manage Music with Catalina/Music App

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