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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.

247 replies

Oct 16, 2019 10:31 PM in response to Fsquire

Did you find a solution? In Music/Edit(I think) I selected all lost then chose "Find Artwork" It found all but about 20%. Most of the rest were so obscure that I had my own folder of their artwork already available, but until that update last night, my Mac was as slow as DSL! Finally loaded the last album just now and I'm syncing my phone... slowly. At least there IS that stupid pie chart.

Oct 17, 2019 4:51 PM in response to jhewell

I also have had issues - album art missing. Half my library missing on my iPhone. Can't sync now can't get my music back on my phone. Apple TV's will no longer stream music to my other three receivers so I can no longer play music throughout my house. There are major things broken. Does anyone know another app/product which we can change to? I am loosing faith in Apple. Has anyone figured out the sync issue?

Oct 17, 2019 7:31 PM in response to Music Lover2

Followup. I restarted everything. Pulled about 50 album covers from the web (they were there before the upgrade) and tried sync again and now have all my album art (24,000+ files) and all my music is back on the phone. Hopefully it will be stable. Prior to upgrade all five of my Apple TV's would play together - now only the two new ones will play together. Others will play by themselves only (I wish they would have told me about this, I wasted considerable time). Tech support indicated that it's airplay two. Hmmmm or is apple wanting you to upgrade. It seems that if the previous OS would play all of them together the new OS should not break it.

Oct 18, 2019 3:46 AM in response to 1Cellar_Door2

SOLUTION TO MY PROBLEM: Apparently, the beeping when trying to have my phone recognized by Finder was something I did, or rather didn't do. I was trying to synch with my phone screen open. When I closed it, I got right in. Now I know I can restore it but I am going to hold off doing anything until I peruse all the cited problems here of synching stuff. Jeez, all my research in resolving my problem did not mention this simple step of turning off the phone screen. But during this quest I have been learning a lot.


HTHS...Hope this helps someone.

Oct 18, 2019 4:10 PM in response to Steven Smith3

All I can say is, if you haven't updated to Catalina, D'ONT!!!! For me, Catalina has been a disaster. My $5000 2017 iMac won't sync with my $2600 XS Max ("...not enough room on my iMac" when I have 1.3TB free) and its stopped my $900 Time Machine from backing up. I've had several very long conversations with Apple Support (been bounced from one side of the world to the other) but its beyond them. I was hoping last weeks iOS update would solve the problem but no.... To say I'm disappointed (and angry) is an understatement..... Here's a suggestion Apple, don't bother having your new product release at the end of the month. Until you get Catalina fixed, I wouldn't entertain the thought of buying another product.

Oct 19, 2019 4:57 PM in response to Noname-v

I have a brand new MacBook Pro (2019), and iPhoneX with 256GB. Managed to sync but if I recollect it was more like a 15 hour process. I now have used aprox 130GB.


There is a small pie chart that shows progress when backing up. Have been able to discover no status bar for the 'sync' process itself. I connected my iPhone today to sync again. Backup was done at 12:05 today, it is now 7:51PM, sync still going on, at least the circle with arrows is spinning. What concerns me is that once again the phone asked me if I'Trust' this laptop -- there was no indication on the laptop to suggest that I needed to respond on the phone.


It seems to me that Apple is trying to push us all to sync on iCloud - unfortunately I cannot and will not put all my info on the Cloud, even if it was free. All this is forcing me to do is consider moving to alternate phones when I do need to upgrade.


I think Apple's software development has made progress backwards over the last few years. It is almost like individual components are now profit centers and they optimize to their own product, so the "Finder team' is trying to do the iTunes job on the cheap and it shows.


I am disappointed, if I could I would return the MacBook Pro and just get a Windows machine for less than half the price - evidently iTunes still works there.

Oct 20, 2019 4:21 AM in response to Steven Smith3

Unfortunately I don't have a solution, but I am having very similar issues. I use my phone as my music device when I teach fitness classes. I update my playlists every week, keeping in them in folders so I know what is current and what is old. I wish I could just add new playlists to the device but I have to go through this whole iTunes/Finder syncing palaver every time. And it just takes too long. I gave up at 50 minutes this morning to sync as I was going to be late for work. Bulky backup music device used. It seems to delete all the music files off the phone every time I sync, rather than just see what it needs to add. That means that if you cancel a sync in the middle, you risk losing everything (which happened to me last week) and today I just lost some things (but unfortunately, most of the music I needed today was missing.) It doesn't seem to delete playlists, or files, but the files are all greyed out and it tells me the music is not available in my region (even though I bought it from a fitness agency in my region and it's legally owned music and I've never had a problem before). It also duplicates/triplicates/quadrup..... etc etc some of my folders and some of the playlists (some now have 9 versions with the same heading but they don't have the right songs in them, nor are they proper folders. It's also dupli/tripli/quadrupli...etc etc more playlists in iTunes. Both my Macbook and iPhone music apps are a complete shambles, and it's taking me 4 or 5 syncs sometimes to actually get all of the music available on my phone. Even though I have meticulously deleted all the extra playlists on my macbook and my phone on 3 occasions, they have all reappeared.


I have slowly been disliking apple as there are so many issues with new updates that just cause a whole heap of extra work and time that I don't have.

Oct 20, 2019 5:27 AM in response to McFazzler

My sync finished sometime last night - not before 10 PM -- so, almost 12 hours. My photographs synced fine, but a couple of music playlists are still missing - now I am scared of starting sync again! Absolute crock.


I would have hoped that Apple would have given us 'finder like' capabilities - show the Music, Photos etc folders on the phone and allow you to drag and drop any music you want from your collection. The only 'new' capability in finder then would have been the summary pages where you could click to make a backup, when you wanted.


But I guess that was too simple. I wonder if Apple did away with usability labs -- where you bring off the street people and watch how they try to do assigned tasks, and what they prefer. I guess not, because the results do not show that anyone paid heed to customer requirements and usability.

Oct 20, 2019 5:33 AM in response to sapper268

I have synced my previous iTunes playlists as I had them previously on my iPhone and the new finder sync results in all kinds of errors, I am getting doubled playlists on my phone and a lot of album covers changed, it is a big mess, I hope APPLE can come up with a solution to it all and fast.


I love apple products, but this is making it very hard to continue loyal....

Oct 20, 2019 10:06 AM in response to Steven Smith3

I am experiencing almost all the same issues after updating a bout three days ago. It is so frustrating. Every time Apple does an update, functionalities get more difficult to interact with or it gets hidden. My iPhone has been syncing for over 8 hours with no progress indicator. I called Apple Support and they were completely useless for me too. I'm so done with Apple. The company has severely declined in the quality of the products they put out since the days of Steve Jobs. Frankly, I don't even think Apple pays any attention to this Community and if they do they just don't give a **** about it's users and their experiences. I'm ready to switch.

Oct 20, 2019 3:51 PM in response to jorgefgr

This is an update to my previous post...


There are two huge groups of items that I keep on my iMac but sync every time with the iPhone. One of them is songs and music videos from Music, the other pics and vids from Photos.


Since iOS 13 and macOS 10.15, I've come to learn that what takes a long time (for me, at least) is the sync up of the pic and vids. Every time I sync, I see the the pics/vids removed from the iPhone only to see them re-stored later. The sync process takes more than two hours every time either wired or wirelessly. With this, what I've been doing is I sync wirelessly during the night. One thing that's problematic here too is, it seems to me, if you add, remove or edit any pic or vid in Photos during the syncing. That, I've seen, stops the syncing process in the middle.


With this said what I decided to do is uncheck the box in Photos (in the Finder) so the pics and vids aren't synced up every time. I chose to keep the contents in the iPhone, which serves better my needs. After this change, syncing the updates to songs and music videos in Music is pretty much instantaneous.


This isn't ideal, but it's better than waiting 2+ hours every time, just to transfer one pic from the iMac to the iPhone.


I'm hopeful that Apple will rectify this in a future software update, though.

Catalina - iPhone sync issues

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