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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 21, 2019 12:57 AM in response to Steven Smith3

Same thoughts and feelings here:

I've maintained my music DB since 2003 on a Mac, Catalina removed long searched (or self-scanned) covers. It also removed covers from the audio books, I don't even find a possibility to save new covers in the iBook.app.

Syncing with the iPhone is not possible tracks are synced or not - not predictable.

Playlist are being doubled.


After first software quality issues Apple introduced the official Beta software program (was it after the iOS 8.x disaster?).

But it's still UNACCEPTABLE not to check basic software features that are needed on a daily basis like a correct sync.


Yeah Yeah Yeahs - Heads MUST roll

Oct 21, 2019 5:52 AM in response to TheAlpsman

Same experience. Playlist folder synchronization is totally broken. Multiple copies of the folder appear on the iPhone, with the copies having incomplete contents. Also, I was getting multiple copies of smart playlists on the iPhone. (I did not see duplicates of ordinary "dumb" playlists. And in a really weird twist, multiple new smart playlists were created on the iPhone that had the name of a playlist folder. Repeated syncing produced more duplicates. Finally, of course, the duplicate smart playlists can at least be deleted on the iPhone, but the iPhone does not support deletion of playlist folders. What. A. Mess.


From my perspective, Catalina is totally busted. I've restored to my High Sierra backup on my computer, and wiped my iPhone and restored it from backup as well.


Seeing all the other similar sync issues here, Catalina doesn't look like it was ready for release. Somebody really dropped the ball on this one.

Oct 21, 2019 6:01 AM in response to Rachel Altos

I've searched the net for other forums for comments describing these issues to glean potential solutions and have found a few. But what really irks me is that none of the publications or so-called tech websites seem to address this issue at all. It's all hunky dory, Catalina is here and it's great kind of coverage. The Mac community seems clueless about it.


My fear is that it will never get resolved, much like the several other issues that have plagued iTunes long-term (e.g., skipping to the next song in the middle of the currently playing song - which still occurs in Music). I've been a long time, ardent supporter of Apple since 1987, but lately my loyalty has been eroding. Steve Jobs must be rolling in his grave.

Oct 21, 2019 8:16 PM in response to WC_Ente

Endless bugs on Catalina at the moment. And bugs that are still present from back to Sierra. It’s just ridiculous. We get .1 updates with new emojis.

I’m a big Apple supporter but I’m starting to lose it.

Installed Catalina from Mojave (Mojave installed fresh about 7 months ago):


- imported hundreds of pictures from iPhone 11 pro on 13.1.3 in photos, selected to delete the files after the import, the files are still on the phone but photos on the Mac doesn’t see them. Had to delete them manually from the iPhone.


- took me 3 days of trialing and testing in order to get the Apple Watch unlock to work. Apple Watch 4gps on 6.0.1


- an old bug where selecting and highlighting text on a PDF is selecting random words instead of the words you select is still there, but reported 7 months ago, still there. High Sierra has the same issue. Not on every PDF, but it isn’t a pdf issue, with acrobat it works fine, it’s an issue with preview app.


- logging into a second user account is breaking the continuity/handoff features on the Mac and iPhone. Apple Watch unlock stops working, personal hotspot stops working, continuity camera not working, handoff not working (works only from Mac to phone not the other way around), only solution is a reboot and log into one single account.


- can’t sync pictures in albums I created in photos on the Mac, they just won’t sync on the iPhone. Tried EVERYTHING, rebuilt library, reboots, nothing.


- switching users takes at least 10 times longer than in Mojave.


- sending a lot of photos with airdrop from Mac to another iPhone or from iPhone to iPhone is not reliable at all, sometimes it ends the transfer and the photos don’t show up, sometimes they are all double and they are always sorted in a random order and not in chronological order.



This is the worse MacOS release ever and the team doesn’t even bother fixing the bugs that are reported on their website. 

All they care about is emojis and wallpapers.

I’m really losing it.

Does anyone else experience the above issues?

Oct 22, 2019 8:50 AM in response to Steven Smith3

I too upgraded only to find that syncing my iPad/iPhone a nightmare. How can Apple get such a fundamental function messed up? Pie indicator is totally lame and only showed progress on the backup then I get the two spinning arrows not knowing if it is syncing or it's frozen. Had it go all night with no syncing done. Rebooted both and now trying again.


We need a proper status bar with stages.

Oct 22, 2019 8:57 AM in response to Pkovacs1

ITunes was clunky, but worked, should have been easy to remove Movies, Podcasts, Books & Photos from it - it’s only code - the remaining code just need to be renamed Music


Not rocket science, but Apple have tried to do additional things like moving the Sync to the Finder at the same time


Just seems at the moment that there’s no focus within the teams, and certainly no communication with normal users

Oct 22, 2019 11:22 AM in response to Steven Smith3

Same issue here. Catalina & iOS, both latest versions of OS's. Cannot sync photos from mac / Finder (Photo app albums) to iPhone 8 Plus.

It's a complete joke that this issue, which has existed on & off for at least 3 years now, hasn't been fixed yet by Apple. Worked fine for a while under iTunes, now the issue is back. Genius Bar & Apple support over phone could not help.


When will Apple listen?

Oct 22, 2019 11:47 AM in response to Steven Smith3

Does Apple bother to do any beta testing these days? Like, BEFORE releasing software updates/upgrades? Just a ridiculous amount of problems with Catalina, and iOS13, Apple CarPlay, Time Machine, etc.. ALL Apple products for crying out loud! Since these updates, I can't back up to Time Machine, I can't sync music to my iPhone and the ability to do it wirelessly seems to be forever gone now, Apple CarPlay nor iOS 13 seem to be able to comprehend the use of their own Podcast app, I can't sync photos and if I'm asked if I "Trust This Computer?" one more time after connecting my iPhone to my MacBook via USB, I'm going to take a hammer to the **** thing. Same thing with CarPlay not working until I unlock my iPhone regardless of the fact that I've chosen "Allow CarPlay While Locked". And I could go on. In my 32 years of using Apple products exclusively, this is the worst it's ever been.

Oct 22, 2019 11:57 AM in response to Todd Templeton

Apple should hire enough new graduates -- with ANY degree -- to test every possible use case of every current Apple product before releasing new hardware or software. It should be an ongoing program. I suspect that back in the day, Steve Jobs did most of this himself out of pride of ownership. It's going to take an army now, and the growth of the testing army will lead the growth of the company. Hardware and software development should report to the testing department and the testing department should report to top management. That way the testing department will always have the final say on whether a new product or service is ready for general release.

Oct 22, 2019 2:54 PM in response to BeldarConehead

I believe it has to do with everything becoming a cost center. So the Manager of the Finder group tries to minimize cost by reducing testing. We see the result 😭


Time Machine is another area where they have messed up. I use two different drives for this. My ‘encrypted’ back up drive could not be seen by Catalina! So I had to reformat and start new backups. Just hope I don’t need any of my old stuff.

Oct 22, 2019 2:56 PM in response to Steven Smith3

First time posting. Using my iPhone Mac XS, watching my 2018 MacBook Pro (all upgrades) trying to sync with my 2018 iPad Pro (all upgrades) and about to pull my hair out with Catalina. First, as the iPad is syncing (and taking forever) the keyboard on my MacBook Pro is NOT working. Brilliant. Also, I keep getting random pop ups saying MP4 video files can’t be played. This is taking FOREVER and there is NO clear indicator what is happening for the sync process. VERY disappointed.

Oct 22, 2019 4:43 PM in response to Lexicon2600

It's probably destructive in some way but I found out today how to achieve sync/life balance. Once the Last Backup date has been updated in the General tab showing that the iPhone backup has completed, with little or no disk activity showing in Activity Monitor and no pie chart progress icon in the left side panel, I can use View > Send Signal in Activity monitor to send a SIGHUP signal to the AMPAgent process. Again, not recommended because I don't know what the effects are, but FWIW that's how I achieve sync/life balance.

Oct 23, 2019 10:45 AM in response to Lexicon2600

It is goofy, but the MacOS side of sync doesn't log anything. However, the iOS side does log the synch process. So you can open the Console, select your iPhone or iPad on the left side and watch the log messages. If you set a search term like "importing" or something like that you will essentially get progress indication so you can see if it is doing stuff.

Catalina - iPhone sync issues

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