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It's not working here, and hasn't since Beta 1. Dragging over the iPhone/iPad doesn't highlight the device, and then letting go on it does nothing, both in the Music & TV app.

For me it’s working. Second option is sync. I’m transferring music and samples to iPhone every day.
 
Hang on, you start off, seemingly saying that "Manually..." option is not checked, then say that you manually transfer. Which is it? If it isn't checked, how are you manually transferring? As that's how I used to have my device, before the beta broke it. Syncing music/video/podcasts in the way I mentioned earlier now seems broken, as on my device, in Finder, it's not seeing anything in my library now. I have to use the Files method I mentioned, and put stuff into VLC instead. For music, I have Apple Music, so that's not an issue for me, but I heavily rely on using iTunes for TV/Films (or now Apple TV app).



It's not working here, and hasn't since Beta 1. Dragging over the iPhone/iPad doesn't highlight the device, and then letting go on it does nothing, both in the Music & TV app.
I manually transfer since the dawn of history and up to Mojave. I’m saying that manual transfer is not possible under Catalina. I thought that was what we have been discussing.
 
I manually transfer since the dawn of history and up to Mojave. I’m saying that manual transfer is not possible under Catalina. I thought that was what we have been discussing.

If you re-read your previous post, you imply that you don’t have the ‘Manually...’ checked, in response to my question asking if you have it checked now (I quoted your specific post that I was questioning), since mine has unchecked itself and wouldn’t stay checked on one of my iPhones.
 
OK...firstly THANKS for this thread. It's infuriating.
Secondly, Todhunter is NOT the only one with this issue.
I simply wanted to drag and drop songs from my desktop into my phone without needing to sync libraries and such nonsense. There was a way to do this up to Mojave through iTunes...although when dragging multiple files from the same album at the same time it would turn each track into a new album (ughhh).
And now the somewhat positive news...i've found a workaround that is supremely figitty but it works for now.
Running Catalina Beta 2 and iOS13 beta with "Manually manage" box checked.

1)

Screen Shot 2019-07-11 at 8.14.46 am.png

2) Click the "music" tab to see the window...

Screen Shot 2019-07-11 at 8.15.03 am.png

3) Drag just first song (track 1 or whatever) to that window but WAIT until you see the green plus sign (+) to appear before dropping or it won't transfer (the plus sign usually appears as you first drag it over).
Then drop it anywhere in that library looking window.

Screen Shot 2019-07-11 at 8.15.21 am.png

4) Confirm on the iPhone that the track has transferred then go back and grab all the other tracks and with green + appearing, drop them in the same place.
The iPhone should creat ONE album with all the tracks in it.
Weirdly, EVERY TIME I do this, I have to go back a third time and get Track 3 of EVERY album as it never transfers over.

Screen Shot 2019-07-11 at 8.16.11 am.png

Hope this is somewhat helpful.
 
So to bring this back up now that it's September, I can seem to still add music manually to my iPhone the normal drag from library into iPhone way. But deleting doesn't seem to work at all, which is bizarre and frustrating.

You can manually delete albums/songs from the Music app on the iPhone itself, but that is a tedious process. I used to be able to mass select a bunch of songs/albums and hit delete.... and they would delete. Now it simply does nothing.

Anyone else have the same issue?

macOS: 10.15 beta 6 (19A536g)
iOS: 13 (Build 17A5821e)
 
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