MacOs Catalina add music manually on iPhone 11

So I did a complete wipe and reloaded all my data on Mojave a few weeks ago because of Catalina being so screwed up in this iPhone file management respect. Has there been any catalina updates to fix any of these issues?

As everyone have said, this is beyond frustrating and ridiculous.

I was able to add the tracks to my iPhone by clicking the already mentioned "manually manage music..." option on Finder.

You go to this horrendous "Music" app, right click on the track you want and you will have the option "add to device". However, if you want to add the whole album, you can't do it. Why this happens? I have no idea: if I can add track by track, why can't I add the whole album at once? This is not even logical.

It took me years to migrate to Apple. But it seems it won't take that long to go back to what I had previously in the non-Apple world: full control.

It is very inconsistent now. After doing every update and restarting several times I am able to click and drag only full albums that were added before the updates. Better than before when nothing would transfer in manual mode. New stuff I have added will not transfer, but shockingly anything newly purchased from Apple Music transfers just fine. I agree the new interface is horrible. Ironically my whole reason for choosing Apple many years ago was because of the music management interface. It was the best in the biz. I have no problem buying music from Apple. But I have 500+ cds I like to listen to on my phone too. This Catalina platform seems to want me to repurchase all of my collection to make it mobile. Not fair Apple. Why do this? Just for a little more money? Stock price? I'd love to know the logic behind it all. Or is this just a dumb mistake by a really dumb software engineer? Sounds like your going to loose some folks over this, or at the very least have a lot of folks time machine back to the last OSX. I'd like to see iTunes come back. I'd like to see it but back the way it was. The interface was easy and very user friendly. See what the next update brings I guess.....

Connect your iPhone to the Mac.

In Finder select the iPhone in the sidebar

In the main finder window it should show your iPhone with tabs for General, Music, TV Shows etc. Select General.

Near the bottom of the window under Options check the box beside Manually manage music, movies and TV Shows and click apply.

Open the Music app. You should now be able to drag songs and albums to your iPhone

If you select individual songs you can right click and Send to Device but if you right click on an album there is no option to Send to Device, only to playlist. If you expand the album you can select all song and right click to Send to Device.

This is an absurd problem that needs a fix.

I can't add an album (via songs) to my device, as the option is greyed out. I can't drag a Recently Added album to my device. This is the very basics of what Music should offer. I've rebooted, updated, wiped my iPhone's music library (200GB) and tried to start over, all to no avail.

When I use finder to try and add music, album artwork is stripped out and individual songs appear as the only track on an album (a fun feature when I have 51 tracks on a new album). When using my phone (XS), sometimes I see the music I just copied over, sometimes I don't.

I don't want to create playlists, I want to manually add albums as an album.

The inconsistencies and the broken functionality is unacceptable.

I have the same problem. My feeling is that I am being "pushed" in the direction of a subscription to the Apple Music service. And a bit violently maybe... At the moment the only solution I have found is to handle my music through a windows machine using iTunes. I tried the solution of "manually managing my music" in finder, and it completely wiped away ALL my music from my iPhone 11. (painstakingly sorted and organised over many hours of work...) The whole thing doesn't make much sense. It seems that I don't get the option to have different music in my phone than my computer!!

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.

This is the best detailed description of what is going on that I have read so far.

the only thing I would add is that the new Sync interface sucks wax fruit. A spinning circle and then a little timer? That’s it?

So much for the details. Apple has got to be reading this stuff. I’m really hoping R&D takes notice and gives us back some of what made iTunes so great. Come on Apple, we know you can do it.

Does not work - that's the original point. Menu choice of "send to device" and the connected iPhone are available but nothing happens. IMHO modern developers haven't a clue what they are actually doing - opinion of a retired developer glad to no longer have to work in the environment

I would just like to add my voice to this one. It's January 26, 2020 and there is no end in sight to this frustrating and horrible problem. I can add music to my iphone, but never the same way i did it last time, i have set my phone to sync over wifi, sometimes it works like that, sometimes i have to connect it, sometimes i have to create a playlist on the music app on the mac and then some other times i have been able to drag and drop directly from the "recently added albums" to the finder on the graph that shows me the storage distribution on the device. it's never works the same way twice and what's worst, sometimes even when it said it works the music doesn't show on the iphone and i have to delete it and add it again for it so show, sometimes 3 times. Listening to music on my phone used to be a source of joy and has now become something i dread and i have to take time to do. I wonder where did "Just works", which used to be what apple used to say about their products went? the current status of this is shameful, please do something.

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)

Hey I feel your pain. I was finally able to get it to work. I replied to the original post, but in case you can't find it, see below:

karawanz wrote:

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)

Hope that works for you too!

It's February and I'm still seeing this same bug. It's infuriating. Is Apple going to address this major bug soon? I can drag and drop all music that I had in my library before Catalina, but anything I added to my music library after cannot be dragged to my iPhone.

Did you try the solution mentioned below?

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)

This worked for me post Catalina with new songs as well.

I have tried everything suggested here and nothing works well at all. I tried the sync and non-sync methods and they still won't add random files of music, not just to playlists but to my phone. I'm on all the latest software updates, so that shouldn't be the problem.

I also signed up for Apple Cloud thinking that would help. It doesn't.

When I have tried to add music/playlist to my iPhone, via the finder and Apple Music, it takes forever and then some files won't transfer so I have to unplug and restart the manual sync. Then the system switches all of the "sync" options (phone and laptop) to "on." Then it starts the process all over again.

This morning, I tried this again:

bandic00t wrote:

Did you try the solution mentioned below?

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)

This worked for me post Catalina with new songs as well.

It totally messed everything up and when I re-synced, of course it took forever and then there were STILL files on the iPhone that I had to manually download in the music app on the phone - playlist by playlist.

I added a CD yesterday and it wouldn't add to my iPhone until I synced. Well, some did and some did not. This was after trying to drag and drop the playlist I made of that CD to my iPhone via the finder. They all should have added since they were all imported from the same CD in the same format.

Speaking of which, there are many audio files that just refuse to sync and/or get dropped manually in the finder. They were fine before this horrible update.

I'm tired of fighting with Apple Music and my iPhone every time I want to add new music. Not only does it not work correctly, but it takes forever. I'm done.

I'm going to look for a third party app/software and simply delete everything from Apple Music and re-upload my music to that.

If anyone has any links to music apps/software, that would be great.

If that doesn't work, the next time I upgrade my phone I'll switch to Android.

Seriously Apple, you really screwed this one up and you don't even seem to care. :(