Can't Drag & Drop music to iPhone in Music app in MacOS Catalina 10.15

I don't think this is going to be the technical answer you are looking for, but I had the same issue and got it working.

Basically I backed my phone up to my MacBook Pro. Then went about restoring my phone and once it could be seen on my computer - I was able to drag and drop all my music. It did clear my iPhone of all songs first.

MacBook Pro 2019, iPhone XS.

Hello jasonvandijk,

Welcome to the Apple Support Communities. From what I understand, there's an issue dragging and dropping music files directly to the iPhone. I'll do what I can to help.

Make sure the song you want to add is also loaded into the Music app: Add and download music on Mac

If possible, try also adding then syncing like normal through Finder: Use the Finder to sync your iPhone, iPad, or iPod with your computer

Thanks and have a great day.

Hi! i found a temporary fix for it. Uncheck the "Manually manage music and videos" in Options first, that'll remove all the music in your iPhone, click Done, then re-check it again.

After that i was able to drag my music back again to my phone. The ones you bought on Apple store remains on your iPhone, it'll have that cloud icon and you just have to download it again.

I hope this helps!!

Just adding on to your response again, I think the video below mostly describes the workaround you discovered, in that unchecking and checking that option seems to register the iPhone in the Finder window, which is now the central hub:

https://macmost.com/sync-your-iphone-ipad-or-ipod-without-itunes-in-catalina.html

Those steps are only if you're downloading music from Apple Music, that is not what I am doing and have the same issue. I have a massive CD collection. I still buy CDs. For years, I have imported these CDs into iTunes and I might change the meta data (titles, album name, track number) to create my own custom compilations. I just tried this in Apple Music and I can't drag these tracks over to the iPhone.

This is in addition to my frustration that when my iPhone, or iPod, is connected now, the Apple Music UI won't let you edit or even play music that is stored on that device. Why are you taking away this functionality? Why are you making it difficult for music lovers to still use your platform?

So what if we dont want to sync, just drag and drop to iPhone like we did in Mojave?

Same question here.

For real? Can't drag and drop to an iPhone like we used to?

I can't believe they'd actually release iTune without this most BASIC of functionalities....

Seriously. I just caught this issue when trying to use iMac to drop songs/playlists to my iPhone for a trip Im taking. And I cant! thats ridiculous - I dont want to use my iphone for EVERYTHING! Aplle bring back this functionality so we users have a larger screen to work with.

Thanks Captcoco, that is a very intriguing solution to this issue. I wonder if that process of backing up and restoring the phone on the new Catalina OS somehow registers the music files in a better fashion, allowing for the removal and re-loading without a problem. It seems like it is worth a try!

That does indeed sound fairly straightforward, thanks! Admittedly, I feel a little nervous about having this process remove all the music from iPhone first, as I have this fear that it won't let me drag all those same albums back over again. But your recommendation seems sound enough, I will give it a try soon!

I'm with Grail047. WTF Apple?

Thank you - that seems a lot easier.