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

I figured it out. In the Music app, your iPhone will appear in the sidebar once connected and you can manually drag and drop tracks on the iPhone icon just as you would in iTunes. I found a bug however, if you import new songs into Music and try to drag it onto your iPhone, it won't work for some reason. But if you close and reopen Music, it will then allow you drag and drop your newly imported tracks.

I think I have a solution, this is what finally got it to work. any new tracks you have, you have to place them in the Music/Media/Downloads-Music Folder. you will notice when you go back to Music (iTunes) you will now be able to drag and drop those songs into your iPhone

I guess there's a very nice workaround for all those missing the basic yet powerful functionalities of iTunes to manage the playlists and tracks on their iDevices directly ...

I have re-installed iTunes on macOS Catalina using a patch programmed by a fairly clever guy over at github.

The patch/app is called Retroactive and not only brings back iTunes, but also Aperture and iPhoto ... ;-)

Info & download: https://github.com/cormiertyshawn895/Retroactive

I confirm this works for me like a charm without problems, so far.

Macintosh HD/Users/Brett(but your name)/Music/Downloads , or you will find it in finder on the Left Hand Side List. It worked well the first time I did it, but the second time I tried to add newly Downloaded Music, it mixed up all the Album Artwork for those Tracks! They had the proper Artwork in Apple Music, but every time I added to iPhone it put a different Album Cover from my collection, was so frustrating!! I Googled for a while and found a Device Manager called iMazing. It's awesome heaps better Device Library Management, even Drag and Drop over WiFi also Backups over WiFi, and manage Playlists on your Device which you are no longer able to do in Apple Music, I will attach the link to iMazing, I do not work for them or trying to make you buy the full version, but this is what I use now for my total iPhone Syncing. I have turned off Automatically Sync Device in Apple Music (Finder) This App works every time and it's so easy to use. Hope you find this helpful

https://imazing.com/

As posted earlier:

Try the clever Retroactive app/patch available at https://github.com/cormiertyshawn895/Retroactive.

I reconfirm this works for me like a charm without problems, so far.

Hey jhewell,

Thank you for using Apple Support Communities!

I understand from your post that you're looking into the options you have to manage music in Finder with your iPhone on your Mac. I'd be happy to help out.

You can view the information below about syncing your iPhone with your Mac in Finder:

Use the Finder to sync your iPhone, iPad, or iPod with your computer - Apple Support

Cheers!

When your phone is connected and open in Finder, under the 'General' tab is 'Manually manage music, movies, and TV shows' checked? Perhaps this setting needs to be applied in order to manually drag your songs onto your phone in Music? This setting was already applied for me.

Ok, so manually sync works for some albums, but not others. I just added some albums that hadn't been on my iphone for a while and these will not be dragged and dropped on the iphone. Others will, though. All hare same format, mp3.

Edit: There seems to be a new feature in Catalina that force you to change the way you sync music. You first have to restart the computer. Not sure why Apple thinks this is a useful feature, but I will probably find out at some point. For now it works fine but remember to restart between syncs. Great! Glad I don't have to retart my car every time I hit a red light....

Ya what the ****. I had to do the same restoring process when I got a new MacBook. Backing up to iCloud or iTunes works for everything but music? why? So I started using an app that comes with Setapp called AnyTrans which is an alternative iDevice manager that actually let me back up my music, BUT NOT playlists. I realize the backing up of music/playlists has never been an option through iTunes but since when has simply updating to a new OS on a MacBook that's already been synced with the same iPhone called for having to wipe the media from it? I, along with most others I assume, use playlists to be able to listen to a particular set of songs or albums without having to search through your library and remember which songs/artists/albums were recently added or added b/w certain time frames. whatever the reason, i dont remember exactly what songs were on my iphone previously and even if i did, going through and adding just the ones you want any time you upgrade your phone or macbook or iOS or OS is nonsensical and unnecessary.

Lastly, half of the time when using the search feature in Music, something i used to do regularly in iTunes sometimes wont even result in finding a song that I know is in my library. I know its in my library because after searching fails, going back to the songs menu and sorting by artist or song name and scrolling through thousands of songs I'm able to find it. and ive had plenty of attempts doing this to make sure i spelled correctly in the search bar. for all the benefits of catalina i cant say theyre necessarily worth losing the simple ability of managing music on your device, especially not for locating music on your own computer. if going back to mojave wasn't such a long process i'd do it. for anyone that hasnt updated to catalina, if your music is one of the main things you use, do, listen to, whatever, I'd highly suggest not updating. I read the same thing and figured how bad could it be. hindsights always 20/20. sorry for the long winded post but had to vent the aggravation this has caused

Try this: https://github.com/cormiertyshawn895/Retroactive ... really ... ;-)

How do you manually drag and drop music onto the iPhone like you would in the past? I don't want to sync my phone and have my phone organization get overwritten due to sync being the only option. Even if I push sync, I get prompted that all other areas of my phone with get removed (see image below), not just the music - I don't want to anything changed on my phone, I just want to add new songs like I use to.

Thanks for the tip, but this was already checked.

However, after tonights update to version 10.15 it works again! Also an ios update so not sure which update fixed it, but at least it seems to be working again! :-)

Totally agree. I can't even expand my playlists on my iPhone or iPod touch and click and drag items from the music app to these playlists. This is concerning. Need another update to show this functionality as I keep getting this message too and don't want to lose my songs.

I already commented on the total disappointment when working with the new Music app ...

Pretty much all features, which actually made iTunes such an effective tool disappeared:

the column browser, the ability to organise tracks and playlists directly on the iPhone, to just name a few!

It's about time to bring these features back, Apple!!

Tried this but still won't let me manually manage songs on my device from iTunes. This may be the most frustrating thing Apple has done. I really wish they would stop controlling more and more things with these devices. I guess syncing is the only viable option but I don't want to do that either.