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Catalina - iPhone sync issues

So I upgraded to Catalina today, and then tried to sync my iPhone (knowing to expect differences with the upgrade due to the departure of iTunes). However, when connected, it just continues to sync, and there is no status bar to show the progress, so I'm left guessing where it's at, what it's doing. etc. It has been syncing now for over an hour, and still no signs of coming to an end any time soon. Any help would be appreciated. Thanks!

iMac Line (2012 and Later)

Posted on Oct 7, 2019 7:56 PM

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Posted on Nov 13, 2019 4:16 AM

Thank you for sharing all this information. I looked at the /~Library/Preferences/ directory and found that I have 56 com.apple.*.plist files. So do you think it is safe to delete them all? Most of them look like they are config type files. I am having a hard time pulling the trigger on the delete button.

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Nov 1, 2019 10:35 AM in response to lunayconsuela

Thanks, found it (search field - should have seen it before!). By the way my wife's phone took about an hour for the update and restored all the music this time. Maybe the bugs are getting worked out. I wish I had a dollar for the hours I spent on the update. Maybe now that the major components have been split off things will settle down a bit...... At least for me.

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Nov 11, 2019 2:53 PM in response to Tung1131

I get the story I am with you it’s horrible water my whole day off. Iphone XSMax 512 wont sync properly plus backup area greyed out. Just very poor. Was going to back up as as to get new iPhone but no way. Said it backed up but when I look it was actually the file was 4 months ago.

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Nov 11, 2019 2:54 PM in response to Douglass Scott

I get the story I am with you it’s horrible water my whole day off. Iphone XSMax 512 wont sync properly plus backup area greyed out. Just very poor. Was going to back up as as to get new iPhone but no way. Said it backed up but when I look it was actually the file was 4 months ago.

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Nov 11, 2019 7:58 PM in response to Steven Smith3

This departure from iTunes has been a complete disaster, A long time Apple fan boy, I am really starting to question my loyalties! The finder sync is awful, never works properly, it is either just hanging, or I am left guessing as to what it is trying to do. Music & TV+ are nearly as bad, you can't search your own library if, heaven forbid, you have added your own files, but it is happy to search the store... go figure eh? I have been trying for nearly two hours to remove two audiobooks & add three more & it's still not done. So, I suppose my question at this point is, how do I go back to my previous version of Mac OS that actually worked!

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Nov 12, 2019 9:10 AM in response to Steven Smith3

So, here's what I'm thinking: Apple just doesn't want to be in the music library manager business anymore. They want to be in the Apple Music subscription business. It literally doesn't matter to them if iPhone music sync is busted, because they don't care about it.


So, if you want a good solution of music library management and syncing, you need to find a company that cares about serving those customers. And that company isn't Apple. I'm currently investigating CloudBeats. They use cloud file systems like DropBox to handle storage management and music file synchronization, while they handle the user interface for playing music. So far, it looks pretty good, but I'm still working on the best strategy for migrating playlists.

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Nov 12, 2019 1:39 PM in response to Rachel Altos

I have the Catalina MacBook Pro Finder sync to my iPhone xs Max recognizing each other. The sync seems to be working with no errors, but.... I have a number of purchased iTunes movies that I can download from the Cloud to my MacBook Pro (late 2013). I have successfully downloaded 3 or 4 of them to my MacBook. I verify they are in my local TV library and play them while disconnected from the network just to be sure. When I bring up the Finder window and connect my iPhone to sync these movies to my phone none of the downloaded movies appear in the list movies. In fact, it looks like the only movies listed are the ones that I manually loaded in the past from DVD to iTunes. TV show that I purchased via iTunes show up in the Folder sync list along with the TV shows I manually added from DVD and they can be sync'd to the iPhone. I am very puzzled by this behavior.

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Nov 12, 2019 4:27 PM in response to 4symmetry

@4symmetry the weirdest thing to me about all of that, is you deleted Catalina and started from scratch correct? Or only wiped your phone to 0? I too have been wondering if wiping my computer and starting from scratch would help, as I was one of many that when installing Catalina it just hung, and did not finish the install process, and after several hours I just pushed power until it cycled. Wonder if I export my library to an external disk, wipe my MacBook Pro, and re import into the library after fresh install, it would work...

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Nov 12, 2019 4:36 PM in response to photoguy7

I essentially rebuilt my MacBookPro. I moved any messages I wanted from folders on my Mac back to the Inbox, saved my Documents, Downloads, Pictures, Music folders onto a spare hard drive. Then I installed Mojave (after deleting the drive etc). Used transfer Assistant to move Settings, Documents from an older TM drive saved a few months back.


Then I replaced the 'old' documents, downloads, pictures and music folders with the more up to date ones. I deleted the iPod Photo Cache.


After the mailboxes were rebuilt, I moved all the old messages from Inbox to the folders I use. iTunes sync works like it used to now!!

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Nov 14, 2019 7:41 AM in response to Pkovacs1

So sad that many people are facing the same issues but Apple doesn't seem to be interested in releasing a single tech note or whatever. It's like they're thinking: to **** with your photos and whatever. And we don't care about your music, just spend 10 bucks on Apple Music (or Spotify, we don't really care). We all miss Steve and The Woz. This is Tim Cook's Apple. I'll still enjoy their cool displays with a linux distro running on it. End of an era.

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Nov 15, 2019 5:53 AM in response to alvarez007

I could not agree more. Trying to synch my playlists with the new macOSCatalina continues to be a nightmare. Firstly the synch message just sat there for over an hour....and did nothing. Secondly, when it did manage to synch I ended up randomly losing many of my favourite songs in several playlists. Thirdly, it refused to synch completely with an older itouch model. Yet another example of Apple prematurely rushing out a new model before it has been properly tested and therefore ignoring their customers' needs. Why do we constantly have to suffer such a poor user experience while waiting for you to send us updates? You seem to have more patches than an A&E Department! When things eventually work, the quality is impressive but your customer care continues to be rubbish.....Shame on you Apple!

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Nov 15, 2019 1:21 PM in response to Fsquire

I'm am CONSTANTLY re-adding Artwork! It ****** me off so much. I don't want a Greatest Hits cover - I want the album or single sleeve art from where the track came from. With over 30K tracks, it took me long enough to get them. WHY isn't artwork burned in to the track with the rest of the metadata?!?

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Nov 16, 2019 10:52 AM in response to Cromiriark

43,439 songs on itunes.....29,817 photos and 785 videos in photos. I am happy i nearly never purchased anything neither on itunes or apple music ( if you can buy something there ?? ). it reconfirms me a lot i did well never to do so, and i probably never will. Did spend a month trying to solve the problem..... the only solution is a total back-up then reset.....and then restore my phone...a i supposed to do that 3-4 times a week ?


The no answer policy from apple is certainly due to the fact.... they ...well i don't know... i just don't get it how you can put something on the market that doesn't work......

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Nov 17, 2019 11:26 AM in response to awoodell

awoodell wrote:

Thank you for sharing all this information. I looked at the /~Library/Preferences/ directory and found that I have 56 com.apple.*.plist files. So do you think it is safe to delete them all? Most of them look like they are config type files. I am having a hard time pulling the trigger on the delete button.

Hey @awoodell,

while I would guess that deleting any .plist files won't break anything permanently, I only deleted a few: "'com.apple.finder.plist' plus any .plist files that start with 'com.apple.' and then have something like AMP or applemedia... after it. They haven't shown up again and I didn't note down their names so I can't tell you the exact name, but those were like 2-3 .plist files."

Hope that helps! Those definitely were safe to delete. But no guarantees! Good luck :)

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Nov 17, 2019 4:18 PM in response to Steven Smith3

I'm also having this issue, called support and they took the issue to a senior advisor, no luck, still no fix, and I have some audiobooks that I need to transfer over to my iPhone and I can't. Apple please bring back iTunes this whole Finder syncing thing is a mess.

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Catalina - iPhone sync issues

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