Can't Manage Music with Catalina/Music App

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!

LaurenKat wrote:

Catalina upgrade deleted my entire iTunes music library of music I had imported 20,000 songs from the last 15 years off of CDs. I do have a 10 year old iPod with the same music I lost, but I don't know how to transfer my iPod music to my new iMac and new MacBook. Anyone know?

See Recover media from an iPod - Apple Community. The principles should be the same with Music as for iTunes.

tt2

Catalina doesn't support manually managing existing content on the device in the way that was possible with iTunes. Sync selected playlists and it should work as expected. If you have media on the device that isn't in your library see Recover media from an iPod - Apple Community.

tt2

See Recover media from an iPod - Apple Community. You'll need to read Music for iTunes where appropriate, and ignore the fact that the screenshots were made on an older version of Windows, have the process is essentially the same: reveal hidden folders, copy files to computer, unhide them, add to library.

tt2

Taking music off the iPod is a bit more straightforward.

1. In the Music App (Formerly iTunes), select the iPod from the "Devices" section of the sidebar.
2. Select the albums or tracks you wish to remove
3. Press the "Delete" key on your keyboard
4. A prompt will pop up asking to confirm that you want to remove the items, click "Delete"

I don't know why but they have seemingly removed the ability to right-click on music once stored on your iPod, so all of the options you can access when right clicking a song in your iTunes Library arent available. Frustrating, but as long as I can add/remove music I can make do.

Apple has forgotten the old rule of "if it ain't broke, don't fix it". But we should keep in mind that we are in a minuscule minority of users who are still opting for a dedicated music player rather than just using a streaming service on a phone.

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?

i too am having no luck finding a way to move music files onto my classic since i went to catalina. maybe with the twice weekly patches that have been coming from Apple they might fix this too.

miss you steve

I have the exact same problem and im soooo frustrated about it! I've spent the last hour trying to figuring this out. WHAT HAPPENED? And to the people saying "drag and drop to the phone icon" No, i dont want to drag and drop randomly, i want to be able to arrange the songs to the playlists that i have. Does anyone know how to do that??

To scottasonicdvx,

Thanks for advice.What about taking music off the iPod? What about dealing with the iPod music library? I don't like clumsy solutions, Apple isn't interested in Classic users, it does not fit into their business plan. Catalina is for iPhone and iPad owners,I loathe smart phones and am not wearing an Apple watch.

Simply must move on is not for me, I will stick with Mojave and am looking at other software like Walt2 or buying an alternative player that is true Hi-Fi.

I found the Finder to be a less efficient method to go about deleting tracks from my iPod.

The window that opens when using this method to manage your music simply displays the contents of your iPod by track name and file size. So you would have to memorize the name of every track you are hoping to delete and can fish through thousands of lines of text to find the right tracks.

Doing it through the Music App allows you to swiftly navigate your iPod Library and remove music efficiently and intuitively.

But both methods do work!

Yep, I'm certainly not recommending manual management for Catalina, in fact I've never been a fan. Syncing with selected playlists is always more powerful and elegant, and it ensures media is kept in the library rather than discarded as some users seem to be fond of doing, only to need to rescue their data later.

tt2

I'm thinking that Apple have found this option and stopped it! I can not see the 'add to device' option any more. Last week I was able to create a new play list and add to old ones and they would sync to my iPad or iPhone. This week, I can delete playlists but I can not add new ones or even add songs to ones that are currently on the devices! Not happy!!!! Any ideas?

Catalina upgrade deleted my entire iTunes music library of music I had imported 20,000 songs from the last 15 years off of CDs. I do have a 10 year old iPod with the same music I lost, but I don't know how to transfer my iPod music to my new iMac and new MacBook. Anyone know?

Sorry to hear about your lost library.

Have you considered trying Time Machine to restore a backup made prior to your software upgrade?

I don't know of it's compatibility with the latest version of macOS, but iRip has been a valuable tool for me in the past. I used it just over a year ago transfer music into iTunes before wiping an iPod.

Have a look and see if there isn't a version of iRip floating around that might still function. Otherwise your best bet would be to find an older Apple computer and boot a compatible version of iRip.

Best of luck! And once you do have your songs again, buy an external HD and keep them safely stored for backup!

Give a try and see! I havent used it in the last two years. Only one way to find out!

Otherwise I'd find a slightly older Mac and use that to rip your music, then a external HD for transfer and backup.

Good luck!