MacOs Catalina add music manually on iPhone 11

If they don’t do that Catalina is a joke and unusable for me

Thanks for the tip. This works at a basic level, although it doesn't take the album artwork with the music files, which I don't like. It's a nice bandaid for now, though.

This is terrible by Apple. i can not manually add music to my iPhone 7. Oddly, i can only add music manually to my old iPod.

How are you able to manually add music to your old iPod? I have an iPod Classic and I'm struggling to figure out how to manage my music library now that I've updated to Catalina. Any tips?

My main problem right now is this: I want to add music to my iPhone, the music app sees my phone but I can’t drag. Then o restart the computer and the music app allows drag. And then it doesn’t.

This was extremely helpful & completely solved my issue.

It’s so lame this fix was not part of the latest update. It’s a way bigger issue than a lot of the other crap they fixed.

I won’t subscribe to Apple Music either. I already have Spotify for that.

Thank you! I had to re-sync it after doing all that but it worked. What a shame that Apple cares so little about its users that it couldn't have done this itself.

Hopeless! I used sync but only the playlists that I choose. Manually doing it is a total disaster. One may be able to add music manually but you have to delete it from your library on your device to remove it. It seems to me that if you have to use the music app and playlists, even to add or remove a single song you have to do it from a playlist and then Sync again.

Steve Jobs must be turning in his grave with what is happening to Apple. In thinking themselves smart I feel that they have disenfranchised at least half of the Apple device users on this planet. The music app is a lemon. Surely they know enough to realise that "If it ain't broke, don't fix it!"

I've had this problem since updating to Catalina (10.15.2 on a 2015 MBP & 13.2.3 on an SE). Any songs in the Recently Added area won't add to iPhone, however, the playlist trick mentioned here works ok. I proved that it worked, then deleted those songs from the iPhone & then proved that I still couldn't re-drag them (I was checking to see if some flag may have been set, or that iTunes had 'learned' - it hadn't). Someone here suggested a restart, which worked but before I did that, I also found that going into Sidebar - Library - Songs, that I could drag highlighted songs to iPhone successfully but still couldn't drag them from Recently Added area (I didn't try doing it from Album or Artist).

Apple - I bit into your products with an iPod 3rd in 2004, & until around a year ago, I thought it was the best thing I'd done technology-wise. My experience has always been bullet-proof equipment coupled with software that worked perfectly well. I don't know what you're doing these days but this is an example of a basic feature that should be ironed out before updates are released. From reading many other reviews, it seems that Catalina has many other issues & you're changing basic functions, where die-hards are having to waste time re-learning every time you put out an update.

If the Darwin Awards did trophies for operating systems, you wouldn't win but, compared to how your products used to be, it seems that, unfortunately, you're getting there. Get the basics right & stop messing about with our Apple OS experience before you eventually force your Customers back to the dark side.

In case anyone is still having issues, here's what worked for me. [iPhone version 13.3, macOS Catalina 10.15.2]

On your iPhone: Go to Settings -> Music -> Turn off "Sync Downloads"

On your Mac: Open Music app -> Preferences -> uncheck "Sync Library"

Now, simply drag and drop songs directly onto your device icon on the left (make sure device is highlighted as you hover over while dropping)

I simply unchecked “check the box” and checked “manual”. Then in the Music App on the Mac I dragged the music to the device on the left bar