Catalina - iPhone sync issues

It seems they stopped using a local media library. I had been keeping my iTunes library on an external volume but that's no longer being used during an iPhone sync. This suggests to me that what we used to own a local copy of is now just a right of online access to the titles we've purchased in the past. That would be like owning a gold certificate instead of the gold itself. This would be more convenient in that I would no longer have to dedicate local storage. If true, however, then our ownership rights to the titles we've purchased have been reduced from that of a freeholder to that of a tenant in common.

I had related issues with Photos library not syncing because I keep my photo library on a folder-mounted external drive. It works in the Photos app, but the Finder-integrated sync thing could not find my Photos library. I think it initializes too early (during login) when my external drive hasn't been mounted yet. While they figure this out, I switched back to keeping my Photos directly in Pictures located in my home folder, because I don't have time to mess with it. Ugh.... my SSD isn't big enough for this s***.

Check that (replying to my own post). The music portion of iTunes didn't so much go away, it just got split out and renamed to Apple Music. Well over a week after upgrading to Catalina, the Apple Music app kicked in and started looking for my media folders. In almost the same way I had previously used to show iTunes, I just now showed Apple Music: Music > Preferences > Files (used to be iTunes > Preferences > Advanced), then browse to your media folders, then tell it to organize folders and such... you'll see.

I would also like to be able to drag more than one file at a time. Or have files that you are dragging hilight the folder icons you are dragging them to. Hopefully Catalina 10.15.2 will resolve any of the thousands of issues with this upgrade

Agree with everything here. Same issues as everyone here.

Aside from the dreadful new process of syncing which leaves you in the dark about progress, I have also 15+ years of music library, over 45k songs, carefully filed, organised and with artwork that I have been updating regularly over the years. It's now trashed. Artwork lost, ton of files wont sync at all, and of those that do, many are greyed out with 'not available in your country' despite them being from my owned purchased CDs. I cant even think where to begin.

So far Ive googled Itunes library alternatives but all of them have a single big flaw. I know its dafte but its actually quite upsetting. My music collection is one of my biggest sources of joy in a joyless world. And Apple have wrecked it.

Steve Jobs will be wincing in his grave with this.

My experience so far: updated to Catalina both on my 2017 iMac Retina and on my 2015 MacBook Air. Transfer of iTunes library to Music has been quite easy with a little bit of scripting. I added an album to Music's library.... so far so good. The troubles started when I tried so sync with my iPhone X. All music has been deleted from the phone (nearly 200GB), waited a whole night and the sync was stuck. Tried again, nothing. Restored the iPhone from a backup made with Mojave, still no music. Synced. No music. Factory restore, still no success. Then I did all the same from my MacBook Air where I have the same library on an USB drive, guess what? Nothing. Always stuck with this circle filling up, sometimes it finishes in 30 minutes, sometimes it takes 4 or 6 hours but there's no way it syncs my music. What's been the solution? Download Mojave from the App Store, installed it on a Virtual Machine, restored the old iTunes library and my iPhone synced everything in nearly 30 minutes. Catalina is buggy AF. I've always been an Apple fanatic: I didn't always agreed with all the choices the company made, but -in the end- I've always found great hardware and a great OS. This time I'm really disappointed: I've lost 3 days and the only solution came to my mind because I'm an IT guy and it was a downgrade! It seems that Apple became Bethesda: release it no matter how buggy it is and maybe fix all the issues in the next months. Really, really frustrating.

There is a status bar in the finder if you show the sidebar. It's a circle that slowly fills in a clockwise motion next to your device name. However, syncing now takes much longer than it used to. I used to be able to create a backup of my phone in about 5 minutes. Now it takes 60+ to sync my phone, even if the only content that has changed since my last backup is new text messages received.

Catalina needs a lot of work to be usable.

I have the same problems. I wish I could just treat the iphone as an external drive and simply drag my tunes over to it. I'm much happier using Amazon HD Music. The sound quality is superb, better than Tidal or Qobuz, better than CD's I ripped into itunes in ALAC (I don't know why this is), and I don't have to deal with this clunky syncing problem. Still, I had several songs from cd's that are not in the streaming services that I'd like to have on my phone. I love Apple, but this is a major fail.

Actually, I found that if you select only the "Manually manage music, movies, and TV shows" under iPhone settings in the Finder, a Manage Storage... button appears at the top right of the same screen. Click this button takes you to the media that are currently on the iPhone. Here you can delete whichever songs you want.

Likewise, with this same manual option selected, you can use the Music app to drag and drop media from the Music Library onto the iPhone icon within the app.

So in effect, you can drag and drop to the iPhone.

I'm producing music with Logic Pro. After the update to Catalina the songs I bounce (convert to MP3 and add to my music library) don't sync anymore with my iPhone. So in essence I can only listen to new versions of a song in progress via finding the file on iCloud or using dropbox .. I'm still hoping the slow sync is just because its uploading my whole library again (is it??) but after all I regret I updated. It wasn't working well with iTunes either, but at least I knew my workarounds .. for the premium I pay for Apple I expect a finished product in the OS, not this mess

I've tried this, and it's inconsistent. I tried to drag a 2000 song playlist, and it only transferred 600 songs. The Finder had a message that said my computer wasn't licensed to play many of the songs, which makes no sense, since they are songs I've ripped from my own cd's. The frustrating part of all this is that there seems to be no reliable logic to how it works.

I am also having the issue where I can no longer sync photos from the Photos app to either my iPhone 7+ or iPad. It has removed the folders that were on both devices. Repeatedly re-checked the desired folders and attempted to sync, then they are unchecked once sync is done.

Perhaps they are trying to force you to pay for more iCloud storage.

It worked (albeit slowly) for me. I unchecked sync when connected. Then when to Pictures, selected folder, said select selected folders and then went back to the bottom and pressed apply.

unfortunately one has to be real patient, my first success came after at least 18 hours.

Whoever was in charge of splitting up itunes should be fired! I've lost half of my artwork. Shouldn't this have been tested over and over again before it went public? Some people (such as myself) put so much time into organizing their music, and it's just lost because of a lack of quality control. Pathetic.

I DID NOT APPLY TO BE A BETA TESTER. I bought my Mac Mini for my media server housing my photos, music and videos. Like most of you, I have spent countless hours organizing, converting my vinyl collection and downloading artwork for over 30,000 songs. Luckily, I have multiple backups.

I travel a lot and visiting car event, on each trip I may take 300-400 pictures which I download to my PC after which I watermark them and reduce the size to 1929 x 1080 which reduces the size considerably then and good enough for viewing on iPhone, iPad and TV. I then copy them to my Mac so I can sync with my devices. Again countless hours and effort but all is safe in the cloud.

This is insane that all this effort may have gone to waste. My iPod classic has not been able to sync since Mavericks and Genius Bar essentially proved it and told me I may have to go back Mavericks for it to work. Ironically, the iPod Classic has no problem syncing with iTunes for Windows but NOT THE APPLE MAC.