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Ventura, Apple Music, and files re-copyuing to my iPhone

Hi. I just migrated from Mojave to Ventura. I’m getting acclimated to Apple Music. I’ve successfully brought my old iTunes library in (thanks to turintest2!). But I’m being stumped by the syncing to my iPhone (14, running iOS 16.6).


I go to the desktop; select my iPhone; check “Manually manage music, etc”


Then in the Music tab, I click Playlists; check off a few playlists I want to copy over; click “Sync music onto iPhone”; and “Selected artists, albums, etc”


Then in the Audiobooks tab, I do the same. When I click “Sync audiobooks…” I get the “Are you sure you want to remove…” prompt. I go for it.


I click Sync in the lower right and the relevant mp3s and audiobooks copy over. 


Fine.


I unplug my phone and check: everything I wanted copied over is there.


I plug it back in. On the General tab, “Manually manage music, etc” is un-checked. Is this what is supposed to happen? My computer won’t remember the setting I selected the last time I had it plugged in?


I select the Music tab. The boxes I had checked before are still checked. So, it can remember what I checked there, so that’s right, right? I check a few more playlists to copy over. I do the same on the Audiobooks tab.


I go back to the General tab and “Manually manage music…” is un-checked. I check it again.


I click Apply. On Step 4, it copies over ALL of my selected mp3s and audiobooks again.


This happens every time I try it. As long as its plugged in, I can add to it, but once I unplug it and plug it in again, this “re-copying every file” routine happens.


What am I doing wrong? I went from Mojave to Monterey and had this issue. So I upgraded to Ventura, and it’s behaving the same way. 


Thanks!

iPhone 14

Posted on Sep 1, 2023 8:25 PM

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4 replies

Mar 31, 2024 4:46 PM in response to Stephen Altobello1

Hi...It's been 7 months since I posted here. I've upgraded to Sonoma. I've left the "manually manage music, etc" box checked and dragged playlists via Music (the way it was suggested above). The duplicating files issue has disappeared, but managing playlists via Music is very unwieldy. I have to manually delete old playlists off my iPhone (fine) but those deleted playlists keep returning. After realizing I had over 70 playlists that I had manually deleted return incessantly, I toggled back to syncing via the desktop level.


In the iPhone window on my desktop, I've done the following:

-under General, I've unchecked the "Manually manage music, movies, etc."

-under Music, I've selected "Synch music onto," "Sync: Selected artists, etc." and then selected the exact playlists I want copied over

And the old problem is there: Once I reconnect my phone, to add some more songs, it copies most if not all of the mp3s over again. It takes upwards of 10 minutes to sync my phone.


I want to respect the way Apple wants us to do things nowadays, but either approach has major stumbling blocks I can't figure out.


BTW, my info:

Mac mini 2018

3.6 GHz Quad-Core Intel Core i3

32 GB 2667 MHz DDR4

Sonoma 14.3.1


my iPhone:

iPhone 14

iOS 17.3.1

Apr 1, 2024 5:30 AM in response to Stephen Altobello1

Hi...It's been 7 months since I posted here. I've upgraded to Sonoma. I've left the "manually manage music, etc" box checked and dragged playlists via Music (the way it was suggested above). The duplicating files issue has disappeared, but managing playlists via Music is very unwieldy. I have to manually delete old playlists off my iPhone (fine) but those deleted playlists keep returning. After realizing I had over 70 playlists that I had manually deleted return incessantly, I toggled back to syncing via the desktop level.


In the iPhone window on my desktop, I've done the following:

-under General, I've unchecked the "Manually manage music, movies, etc."

-under Music, I've selected "Synch music onto," "Sync: Selected artists, etc." and then selected the exact playlists I want copied over

And the old problem is there: Once I reconnect my phone, to add some more songs, it copies most if not all of the mp3s over again. It takes upwards of 10 minutes to sync my phone.


I want to respect the way Apple wants us to do things nowadays, but either approach has major stumbling blocks I can't figure out.


BTW, my info:

Mac mini 2018

3.6 GHz Quad-Core Intel Core i3

32 GB 2667 MHz DDR4

Sonoma 14.3.1


my iPhone:

iPhone 14

iOS 17.3.1

Ventura, Apple Music, and files re-copyuing to my iPhone

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