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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

Jan 31, 2020 2:37 PM in response to DSLunsford

wireless sync doesn’t work, plugged in sync worked but it took me 4 hours and 6 attempts.

its just ridiculous.


iPhone 11 Pro and MacBook 2016, not vintage devices.. if I add the fact that the noise cancelling on my airpods pro is ruined with the last firmware and my HomePod is the dumbest smart device on the market, sorry but when I’ll need a new laptop I’ll go for a different brand and I’ll install Linux for a third of the price and I’ll look around for a decent smartphone from some other brand. I’m absolutely done with this.

Jan 31, 2020 2:53 PM in response to rider88

I have 2012 Mac Mini and once upgraded to Catalina, it stopped syncing my 2 iPad Pros, iPhone 6 Plus, 7 plus not to mention my iPod Classic gen 7 which hasn’t synced in 2 years.


using Boot Camp I installed Windows 10 on the Mac Mini, moved my library to Windows compatible external drive and 23,000 songs and 18,000 photos synced in 1 hr with a full status bar let me know what is going on. And guess what, it synced the iPod Classic.


what the **** is wrong with Apple when their products don’t work with each other?

Feb 1, 2020 6:11 AM in response to leobond77

Agreed! I've attempted to let my iPhone sync overnight the last two nights to ensure it had time and no success. I can see the iPhone in Finder and I have new hardware (iPhone 11 Pro, MacBook Pro 2019). This is absolutely ridiculous!!!! In the iPhone window, I see spinning circular arrows... In Music, I have an empty pie circle next to iPhone and the word syncing at the bottom of the page. This is the last time I upgrade OS before waiting a few months for Apple to clean up after themselves. It's said when Microsoft products are actually more innovative and stable than Apple's. I am extremely invested into Apple's ecosystem, but if they're going to treat customers this way, then it's time for a change. I feel we simply can't trust Apple's quality anymore.

Feb 2, 2020 7:50 AM in response to Pkovacs1

So still no fix for duplicate photos showing up on my phone after syncing with my iMac Library, I guess no surprise.


One of the things the I see that seems so wrong is when I sync my iMac photo library with my phone, the sync process first removes all the photos on my phone then updates and places them back on the phone. Why wouldn't the sync process just compare the two photo databases and just update the changes. Seem pretty basic to me....


I would like to have my entire library on my phone, that is why I purchased the 250 GB option on the phone, but with the sync process working the way it does, it just takes too long, plus it isn't accurate. As I mentioned, duplicates show up on the phone.


Feb 2, 2020 8:17 AM in response to Rod Janes

I gave up. I had numerous problems with syncing photos and people being recognized- takes days for the library to be read after waiting days for the photos to sync. It’s not like I have a ton either - about 8 thousand. It was with night Sierra and iTunes on a 7. I don’t use the cloud or iPhoto but sync with a cable and straight folders from iTunes - now finder....


spent hours and hours on the phone trying to just get it to work the way it should and used to - with no luck.... gave up. Heck, every time I’d plug in the phone in the phone, it’d sync 400 to 4000 photos every time even though I’d made no changes or additions.


id switch back to MS if they had us based cs that you could ever get on the phone (without having to log in to another ID and password and pay extra for) AND understand and if I didn’t have to use apple calendars


are your pics in the cloud? Mine aren’t. I know it’s weird, but it seems to me that it’s intentional to get users to move to the cloud, ie to pay for more storage.

Feb 2, 2020 5:40 PM in response to jhewell

So I burned about 5 cds into library using music app. Deleted about 30 - 50 megs of synced pictures from sync folder and plugged in to sync. 2.5 hours and still syncing - I guess. All I see are the little circles going around. Wait... the arrows stopped spinning. And then the pie filled in. I’m done. Oops, guess not - the arrows are spinning again. Hummmm.



R.EALLY ?!!?

Feb 2, 2020 7:16 PM in response to mrchntmarine

So right after the last sync, it didn’t get an album for some reason. I then re added to library then re synced. About 45 minutes of music, should have been any other changes. Took 1 hour 20 minutes.


so here’s something weird. Maybe a coincidence- on both syncs i left the screen on the summary page and syncing music. When things didn’t move I started going to different tabs, tv, files, etc. when I went to music then back to summary, the circle syncing arrows changed to the pie then finished shortly afterwards. Like I said maybe a coincidence but it seemed like it was stuck until I went to the music tab and it then moved. Whatever..... 1 hour 20 is a joke.

Feb 25, 2020 2:11 PM in response to Steven Smith3

Having similar issues. I think it may be linked to the fact that Apple Music moved all my music to icloud (despite my Preference settings not allowing this!) and now i get error messages saying I can't do certain functions because my music is not recognised as being on my computer. (the same computer I've had for the past 7 years) So I'm left to ask if Apple music has misappropriated all the music i paid for on iTunes as i now can't amend or add to my playlists or burn playlists to CD because my thousands of songs that i purchased from iTunes are so longer recognised as being on my computer. How is this possible? So, do I have to re-download those thousands of songs back on to my computer? Agree this is a debacle and something Jobs would not have allowed to happen. Help!

Feb 25, 2020 3:32 PM in response to AUS250

It's both scary and obnoxious the changes that Apple allowed themselves to make on our iOS and Mac OS devices with Catalina and iOS13. My least favorite was hiding all my root level (which is where I've kept all my important files since the mid-1980s) to an obscure folder called "Security". I just wonder how many people lost or thought they lost all of their files. It reminds me of the way a company IT department takes liberties with company computers, but these aren't APPLE'S computers!

Mar 7, 2020 10:46 AM in response to Steven Smith3

After my 10.5 year old 2008 MacBook Pro died, I finally upgraded to a 2019 MacBook Air. Getting everything setup from my external drives was fine. The initial sync with my new iPhone 11 Pro was fine. I ripped 11 new CDs recently and wanted to update my phone before hitting the gym. It's taking forever! No status bar, but the Activity Window claims everything is still syncing. I just did some research and found that sometimes the status wheel shows up in the Finder and sometimes it doesn't. Found an AppleToolBox article for tracking the status through Terminal, but the command didn't work for me. This is incredibly frustrating. I'm really feeling like Apple is designing the manual syncs to take a longer time to sell people on Apple Music and purchasing Cloud storage for having your music stored in iCloud, which I just DO NOT want to do. So incredibly frustrating not knowing how long this sync is taking or if it's even syncing correctly. For all I know there could be an issue with the sync and it's not telling me!

Catalina - iPhone sync issues

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