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Question: 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)

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Oct 12, 2019 4:27 PM in response to Steven Smith3 In response to Steven Smith3

Catalina is definitely a step back, it is full of bugs and issues. Cannot properly sync my photos, it is either all or none. It is a total disaster. Called the Support number and they are clueless, try to bounce you around to different people and none of them know what is going on. The same thing at the apple store, a very rude person at the front at Short Hills on 10-12-2019 made me call support on the phone at the front of the store, even though I told him that I had already done that, then as I am walking out without being helped and visibly upset, he tries to tell me that he will get a sales associate to help me, when I asked him before that I needed anyone to help me, so I left without even saying goodbye.


I am sorry to say that Apple is no longer a trustworthy company; it no longer innovates, only tries to make things more and more complex and only in a way that benefits them. I currently own 2 iPhones, 2 iPads, 2 Apple Watches, and a MacBook Pro but this is the end of the line for me. I am officially fed up with their nonsense. It will never be what it once was.

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Oct 9, 2019 7:52 PM in response to Douglass Scott In response to Douglass Scott

It's not better than nothing. Tried syncing my iPhone through the updated Finder app courtesy of Catalina. First, it deleted half of my music off of my iPhone (approximately 100 GB worth). Now I see the pie chart and its moving tremendously slow. Is it syncing music right now? Is it frozen? Is it just doing nothing? So dumb. Guess I'll just stare at the screen and wait for hours. My old iTunes would sync in under three minutes flat. I thought one aspect of Apple ditching iTunes was to make it easier to sync through Finder but this experience has been awful. Steve Jobs would have never let this OS off the assembly line. Mac model is Macbook Pro 15 Inch Mid 2014 and iPhone is new iPhone 11 Pro Max.

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Oct 10, 2019 9:11 AM in response to Fsquire In response to Fsquire

So update. It took over two hours to resync my phone since it had to re-add all of my music to it (it also erroneously duplicated a playlist). Now, 70 percent of my Album Artwork is missing from my Music App on my phone (I still need to check to see if its the same on my MacBook pro). We're talking about nearly fifteen years of keeping an organized library with associated Album Artwork for thousands of songs.

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Question marked as Helpful

Oct 9, 2019 7:52 PM in response to Douglass Scott In response to Douglass Scott

It's not better than nothing. Tried syncing my iPhone through the updated Finder app courtesy of Catalina. First, it deleted half of my music off of my iPhone (approximately 100 GB worth). Now I see the pie chart and its moving tremendously slow. Is it syncing music right now? Is it frozen? Is it just doing nothing? So dumb. Guess I'll just stare at the screen and wait for hours. My old iTunes would sync in under three minutes flat. I thought one aspect of Apple ditching iTunes was to make it easier to sync through Finder but this experience has been awful. Steve Jobs would have never let this OS off the assembly line. Mac model is Macbook Pro 15 Inch Mid 2014 and iPhone is new iPhone 11 Pro Max.

Oct 9, 2019 7:52 PM

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Question marked as Helpful

Oct 10, 2019 9:11 AM in response to Fsquire In response to Fsquire

So update. It took over two hours to resync my phone since it had to re-add all of my music to it (it also erroneously duplicated a playlist). Now, 70 percent of my Album Artwork is missing from my Music App on my phone (I still need to check to see if its the same on my MacBook pro). We're talking about nearly fifteen years of keeping an organized library with associated Album Artwork for thousands of songs.

Oct 10, 2019 9:11 AM

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Oct 10, 2019 3:04 PM in response to Steven Smith3 In response to Steven Smith3

I have struggled to even reply to this forum ! iMac playing up and iPhone won't sync. Playlists are being duplicated and triplicated but other playlists cannot be added to my phone. Photos won't update or sync !! These aren't the cheapest pieces of kit on the shelves but they are now performing like lower end cheap products. I could type all night about the problems that I have on my iMac!! I have to say if they don't sort this out quickly I will seriously consider moving away from Apple/Mac products

Oct 10, 2019 3:04 PM

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Oct 11, 2019 3:18 PM in response to Steven Smith3 In response to Steven Smith3

Podcast sync is SO broken that I am losing faith in Apple's ability to release a quality product. This is alpha quality code. Either the podcast does not sync, or it creates a new "untitled" podcast on the phone and adds the podcast over there. Of course, the newly created podcast is not in my station list and I don't see it until I go looking for "untitled" podcasts. What a piece of garbage this is... I wish I had NEVER upgraded to Catalina.

Oct 11, 2019 3:18 PM

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Oct 12, 2019 4:27 PM in response to Steven Smith3 In response to Steven Smith3

Catalina is definitely a step back, it is full of bugs and issues. Cannot properly sync my photos, it is either all or none. It is a total disaster. Called the Support number and they are clueless, try to bounce you around to different people and none of them know what is going on. The same thing at the apple store, a very rude person at the front at Short Hills on 10-12-2019 made me call support on the phone at the front of the store, even though I told him that I had already done that, then as I am walking out without being helped and visibly upset, he tries to tell me that he will get a sales associate to help me, when I asked him before that I needed anyone to help me, so I left without even saying goodbye.


I am sorry to say that Apple is no longer a trustworthy company; it no longer innovates, only tries to make things more and more complex and only in a way that benefits them. I currently own 2 iPhones, 2 iPads, 2 Apple Watches, and a MacBook Pro but this is the end of the line for me. I am officially fed up with their nonsense. It will never be what it once was.

Oct 12, 2019 4:27 PM

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Oct 12, 2019 9:19 PM in response to Steven Smith3 In response to Steven Smith3

I am having the same problem. I have always used itunes to manage my music manually instead of syncing because it allows me only transfer the songs that I want onto my iphone, however after upgrading to Catalina, I am unable to do so. I checked the box where it says "manually manage music" but it doesn't allow me to do so. As result, I select the sync my music option, but it has already been 2 hours and it is still syncing (it only took a couple minutes to do in the previous Mac OS) to make matter worst, it does not even have a status bar to show how long it still needs to complete the syncing ! It is totally unacceptable !! I currently own one mac mini, one macbook and one iphone, but I am seriously considering switching to Windos and android completely to avoid this apple mess. I wish I had never updated to Catalina!!

Oct 12, 2019 9:19 PM

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Oct 13, 2019 4:49 AM in response to Steven Smith3 In response to Steven Smith3

iMac A2116, iPhone 6 Plus, 64GB

iPhone constantly syncing. No progress status bar icon. No pie chart progress icon.

iPhone memory bar shows as full (should be max 60% full). I have no idea what the extra 40% of DOCUMENTS AND DATA are.

Only files I can find add up to 719 KB


I upgraded from an 8 year old Mac to this one. Mac is 2 months old. So far I've had 4 very long sessions with Apple help for slow running, crashed Catalina update etc.

So disappointed with my purchase.

Oct 13, 2019 4:49 AM

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Oct 14, 2019 6:34 AM in response to nurjhan In response to nurjhan

Hi nurjhan I was able to recover my playlists following a long call with Apple support. I’m still having all sorts of problems but don’t despair they might at least be able to help with that 🤞There is no point in me trying to explain how because I don’t know due to being a technophobe 🙃

Oct 14, 2019 6:34 AM

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Oct 14, 2019 8:53 PM in response to Fsquire In response to Fsquire

All I can think of is:

  • Steve Jobs is gone and stringent, golden-rule pre-release testing seems to have died with him. I noticed this difference in the first MacOS release following his passing (Yosemite), which bricked my MacBook for about 3 months.
  • Microsoft is no longer serious competition to Apple, thus removing from Apple at least that one big incentive to excel.
  • Respect for the user's time has gone the way of Microsoft and its intrusive, uninterruptible updates. Time Machine and now iPhone syncing have become glacial and opaque. Time Machine is at least interruptible but without detailed status, it's hard to know when to interrupt and defer an iPhone sync. I'd want at least to know that the backup completed.

I expect Apple will be full of surprises in the coming years but it seems now to be settling into the long, shallow plateau of an old-growth blue-chip company. Maybe one day they'll be overtaken and bought up by a resurgent IBM.

Oct 14, 2019 8:53 PM

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Oct 15, 2019 7:17 AM in response to Steven Smith3 In response to Steven Smith3

Same issue here, so I decided to just wait it out. Several hours later waiting to sync 30GB of music, I received this error with no recommendation or details:


The iPhone “iPhone” could not be synced because the sync session failed to finish.


Unreal... So... basically, it doesn't work.

Oct 15, 2019 7:17 AM

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Question: Catalina - iPhone sync issues