In Catalina, how do I "manually manage" music with iPhone and Finder

I am having the same issue, and it's incredibly frustrating. Note my issue is with an old iPod Nano. (yeah yeah... it's my way of disconnecting when I go to the gym.)

So there are two general ways you can try to do this -- Syncing, and Dragging. I'll go through the experience with both.

When Syncing...

In Finder, I have "manually update" checked, but it still threatens to erase everything when I click Sync. No! I don't want this!

Now, let's say I try to drag music tracks over to the iPod.

There are two ways I have found of doing this, and neither works (note, it actually does weirdly work for some tracks, but not others):

1) Dragging the music FROM the music app TO the iPod icon in the sidebar of the Finder

When I do this, it only lets me drag to the lower icon, which says "iPod" (why are there two icons??? no idea). It updates the music THERE, but then I can't find it when I disconnect the iPod.

2) Dragging the music WITHIN the music app to the iPod icon in the sidebar of the Music app

This is similar to the last experience. It looks like I am adding it to the icon (a little black circle appears as if it's updating), but then I don't see it when I disconnect the iPod.

WHY ARE YOU DOING THIS TO ME APPLE. I AM SO **** ANNOYED!!!!!

And how in **** do you see the folders and playlists in the iPhone?

If I want to check whether 1 song is part of playlist?

Everything is mixed up together.

Where are the playlists on the device shown?

Thanks for any light

Yes, I'm updated (10.15.2) & I can see my column browser in the Music app, I'm talking about seeing/accessing/editing what's on the iPad (or iPhone) via the Column Browser. I prefer sorting the songs by the Date Added column, no can do now. I guess I'm saying I want the same options in the iPad window as I have in the main Music Library window. All I'm seeing is this:

But thanks for your response!

PS - Could they come up with a more ambiguous name for the program as "Music"? Discontinuing the name iTunes is as good of an idea as "New Coke" was.

I "manage to manage" the music on my iphone, but I have to reboot the computer ever time I want to manually drag tracks/albums to the iphone or ipad. Ever item (Iphone, Ipad and Macbook) have the latest updates. i really don't understand how Apple after 3 months haven't been able to fix the issues with manually managing music, which had become extremely manually and painfull. Maybe they want us to autosync, but my Macbook can't hold all my music alongsie everything else that is on it (512 GB SSD). Besides I rarely ever listen to music on my Mac so I don't need or want it there.

-iau

Not helpful if one is trying to manually manage one's music, rather syncing their device with the computer. Please answer the question asked.

Hmm, it doesn't work for me. I end up creating a playlist from the album I drag and drop since I can't drop it on the iphone icon, but the whole sidebar only. Have tried restarting a few times.

This doesn't work for me. I can't drag anything to my iPhone and restarting Music didn't change that.

How do you delete music or playlists from your IPhone and iPad in finder. Cannot figure it out.

Octoblocks: I'm having this exact same issue. Can you explain where the Music/Media/Downloads-Music Folder is? Thank you!

I have this same issue -it has basically made my iPhone worthless for music. Time to switch to Android!

Hmmm ... strange!

In my case iTunes works exactly as before.

There‘s also a version 1.2 of Retroactive available in the meantime.

Exactly!!!

OK Boomer....

Fantastic! It worked. Back to iTiunes :-). Thank you for sharing!!

Glad it helped!

Don't forget to also thank the programmer ... ;-)