Catalina - iPhone sync issues

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.

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.

Hi all,

I've struggled with this sync problem for the past 48h but I fixed it! I'll let you know how, maybe it'll work for you too!

Info: I'm using an Iphone 8 Plus + a MacBook Pro 15" 2018.

Background/Problem description:

Since I upgraded my MacBook to OS Catalina, iTunes was gone. I previously had had my iTunes library on my external hard drive, which isn't possible at least for audiobooks now that audiobook management moved to iBooks.

So I added some audiobooks to my internal MacBook drive/SSD via the iBooks app and then tried to sync my Iphone using the Finder. No luck. It would sync for 3-4 hours and the audiobook wouldn't transfer in the end. A lot of the times, I couldn't stop the "sync" which seemed like it would just go on for forever, and had to unplug the Iphone without ejecting...

Things I tried to fix sync that didn't work:

• Reset my phone and deleted all content + restored from backup
• Reset my phone and deleted all content + started fresh
• Upgraded to iOS 13.2.2
• Bought an original Apple USB-C to Lightning cable
• Used my old Lightning-USB cable and a USB-C adapter

Nothing worked, nothing changed.

I read a bunch of things on the internet and then, in combination, did these things:

THE FIX:

1. Eject and unplug phone
2. Eject and unplug any external hard drive that you don't need
3. Open Finder app
4. Click on Go > Go To Folder from the top menu
5. Type in ‘/~Library/Preferences/‘ without the quotes and press enter
6. Delete these files: '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.
7. If you have any photos that you sync from your MacBook to your Iphone, go to the folder on your Macbook that contains them. In my case, that was under Photos/foriPhone8. Search for a folder named iPod Photo Cache, and delete it. Don't worry, you won't break anything by just deleting a cache file :) Also: Yes, it's really called iPod Photo Cache, even if you have an iPhone only.
8. Press Cmd+Alt+Esc and in the pop-up window click on Finder and click "Relaunch".
9. Open a Finder window
10. Connect your iPhone to your computer and wait for it to appear in Finder
11. Sync.
12. Rejoice! 😃

For me, those steps let to a flawless sync within 5-10 minutes!!!!

Credits to these sites for contributing part of the solution:https://appletoolbox.com/items-could-not-be-synced-see-itunes-for-more-information-error-fix/

https://discussions.apple.com/thread/3407102

https://appletoolbox.com/items-could-not-be-synced-see-itunes-for-more-information-error-fix/

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.

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.

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

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.

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!!

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.

FWIW, you should send suggestions to Apple via:

Product Feedback - Apple

for one sent them the following:

-Popup the iDevice window when the device is connected. Currently,

I plug in my iPhone and wonder if anything is happening unless I actually

open a finer window and select the iPhone. Seems like it should have been

a no-brainer.

-Pop an icon on the desktop with a process bar on it, much like is done when

downloading apps from the App Store in launchpad.

-Also, an actual progress bar in the finder window showing all the steps taking

place like it did in iTunes instead of that tiny pie cart next to the sidebar icon.

I have been having similar problems. TO mitigate the issue, I have unchecked the Photos tab (I have about 30GB of photographs).

After doing this: Backup took from 5:15 to 5:20 yesterday- which is acceptable.  Today I used a USB C to Lightning cord.  Back up took 3 minutes!

Auto sync selection was remembered across boot ups.

Suggested steps.

1. Disable autosync on connect.
2. Select what you want to sync - Music, Photos etc to minimize sync time
3. Press ‘Apply’ - OR - ‘sync’ on General Page.

I did find duplicates in my Podcasts folder on the phone yesterday. I plan to check it again and delete them.

NOTE:  My iPhone asks “ Trust this Computer” every time it is connected.  Make sure you answer this!  I hope Apple SW mavens remove this feature - why should this be required if both devices (Computer and Phone/iPad) use the same AppleID.  Even if you think it is needed, then once, NOT EVERY TIME.

I fervently hope that Apple QC improves, and they restore the functionality that iTunes gave us.

I installed Catalina and the woes began.

1. Microsoft office does not work - bought the new 2019 version so am okay
2. Some utilities I use (file rename) etc did not work, downloaded some substitute so okay
3. iTunes does not work, the substitute is a PITA - but I can live with it just barely.
4. Can not connect to public network like at Panera etc - shows connected, but the screen to accept and go to Internet does NOT come. iPhone connects fine. Spent an hour with Apple support. Connects if I go into safe mode but that is not something I want to continue.
5. With the new BackBook, it was recommended that I encrypt my HDD, did that, then also recommended that I encrypt my Time Machine drive, I did that too. On upgrade to Catalina this encrypted TM back up was NO LONGER USABLE. SO I had to delete it and start afresh - result -- lost all my TM from when I bought the laptop earlier this month. Fortunately I have a second drive that I use for TM backups - I did not encrypt it as I leave it at home when I travel.

So:  Need to make an appointment with the genius bar so they can fix it, possibly reinstall Catalina or maybe go back to previous OS. My preference is to go back - only problem remaining is how to retain all my emails (from Catalina update onwards.

RECOMMENDATION: Do NOT upgrade to new OS until their next point release

Whit MacOS Catalina 10.15.1 I was able to Sync my music again:

1. step

I removed all music on the iPhone (go to iPhone memory)

2.step

sync over finder

control:

checked that all playlists had the same count of tracks in iTunes and on the iPhone

That was OK

Already altered playlist Icons or covers are still altered. :-(

My first iPhone 11 sync with Catalina was very problematic as well... My situation is particularly complicated for the new "itunesless-sync" because I store my iPhone backup + my Photos Librairy on an external device, which wasn't connected when I tried to sync for the first time in Catalina...

What fixed my situation was to do the following :

1. Disconnect phone from computer & Wifi (so it doesn't Wifi Sync or sthg)
2. Open "Photos" so it can update the library, then close it. This can take time.
3. Make sure my previous iPhone Backup is in place (which shouldn't be a problem for 99% users, stored in the usual local storage "Mobile Sync" folder)
4. Connect phone and let it sync, or sync it once before changing all the sync-options/music/Photos selection... just let it do its first sync & backup (patience). As long as you see the "sync arrows" spinning or the pie-chart moving next to your connected device, wait some more (took me a good 30min).
5. Then start changing / adapting your sync options and medias... hopefully it'll go fast and without hickups

I gave up on Catalina and moved back to Mojave. Took three reinstalls to get everything set.

1. The first time, install done at Apple Store - Safari would not work and so had to do a fresh install.
2. Fresh install worked fine, but Contacts would not sync, also the 'On My Mac' folder in iMail was missing. Managed to sync contacts, but all groups would show up multiple times. Two hours with Apple Support and several work arounds later, I decided to do another fresh install.
3. Third time was the charm -- everything is working as expected. iTunes is working great, everything is now sync'd up.

I plan to stay on Mojave for at least another two, or more months. Frankly I just bought the MacBook as it is touted to be easy to work with, everything works etc. I am now very skeptical about SW development at Apple.