MacOS Catalina does not sync photos with iOS Devices

On March 24, Apple published a new procedure entitled ‘Resolve issues caused by changing the permissions of items in your home folder’ (see link below). Last week, the Apple support person I have been dealing with contacted me and asked if I would ‘test drive’ this procedure to see if it solves any of the multiple issues I’ve been having with Catalina and the syncing of Photos with my iPads, and syncing my iPods to playlists in Music.

To get to the point: it solved just about everything!

Background: Upgraded to Catalina in December. Had many of the same challenges others are experiencing: only syncs all photos/albums to my iPad Pro (at first, I couldn’t even get Catalina to recognize the iPad); can’t sync a mix of albums; takes forever to sync; very flakey and unreliable syncing of my iPods, etc.

Configuration: late-2015 27” iMac running 10.15.4 syncing via USB cable (no iCloud involved) to a 2017 10.5” iPad Pro running 13.4; 4thgeneration iPad running iOS 10; iPod Classic and Nano; and iPhone 5s and 6s with latest OS that each will run.

All images are stored in the Photos library. Not dealing with referenced images. This is a critical point, as I earlier moved my almost 15k referenced images into Photos to address an ongoing issue of the links to the referenced images getting severed in Photos. In hindsight, this was also likely a permissions issue.

I have not tried to sync pictures to an iPhone, so I can’t confirm if that problem is fixed. Images download to Photos on my iMac from my iPhones without any problems.

Prior to going through the new permissions procedure, we ran the following on my iMac: Booting into Safe Mode, resetting the NVRAM, and resetting the SMC. Also did a minor clean-up of my album hierarchy in Photos.

Did these preliminary steps help with the fix? Don’t really know, but they did give me about as clean a machine as possible before repairing the permissions.

With this procedure you use Terminal to access the Repair Home app. After repairs are complete you install a new copy of your current OS. This is a direct replacement and does NOT require any, at least for me, resetting of preferences, moving files, etc. Very simple.

With the procedure I went as far as Step 7. Did not need any of the ‘If the issue persists’ steps.

IMPORTANT: Because you are trying to fix issues that involve Photos there are two critical, not documented, steps after Step 7:

Step 8 - Immediately after login to the updated OS, hold down the Command and Option keys and launch Photos. Repair/restore the Photos library. This can take some time and for me it stalled at 99% for 3-4 minutes. It did finish.

Step 9 - Immediately after the Photos library repair is complete, restart your computer.

Now you can test and see if this has solved some or all of the issues you are having.

After this fix I can sync any combination of albums to my iPad Pro. Even my six-year-old iPad running iOS 10 actually syncs, very slowly, however. iPods sync quickly and correctly, although some times the sync doesn’t take on the first attempt and ejecting and reconnecting the iPod is required.

Why did this work, at least for me? In conversation with the Apple support person, he highlighted the critical role permissions play in the working of the Mac OS. Over time permissions get corrupted and/or just do not function as required. At the start of the support article there is a long list of problems caused by permission issues.

I am guessing here, but possibly the major changes Catalina introduced accentuated any underlying permission issues with the Home folder. The new process of syncing Photos and Music with various devices via the Finder was part of the ‘collateral damage’ of such a radical OS change.

My suggestion is that if you are currently working with an Apple support person you first discuss this procedure to confirm it makes sense for your particular situation. And as always, don’t try this unless you have a current backup of your system.

I hope this process addresses some of the multitude of issue out there relating to Catalina and syncing.

Here is the link to the support article. Good luck!

https://support.apple.com/en-ca/HT203538

I've had a similar experience:

1. Some albums still say "syncing"
2. Some albums have duplicates (better than none)
3. After removing and trying to re-add one of the albums with duplicates, it won't resync.

I did submit bug report for this too, so I'd recommend everyone seeing issues do the same.

Who marks it "solved", an Apple representative to just some one like the rest of us having the same issue but something happened to work for them?

I have updated all of my devices but have not tried as yet to sync my iPhone Xs with my iMAC. I was able to get it to sync some time back but only by moving some of my albums out of folders and placing them directly underneath my albums. I will give it a try sometime today, since like everyone, we are to stay home.

Thank you for the new thread.

Phoning hours and hours with the Apple support. We're already talking about the weather and our hobbies, but the support can't provide a solution! It'S just gathering information to escalate it to the senior support. I'll see, bit I don't think they solve anything.

It is really disappointing how Apple messed up their formely good software.

I am still having the same trouble. I have been syncing one album at a time having removed them all from my iPad. Sometimes it works and some time not. It appears to be random as to which albums sync and which do not. Sometime most of the pictures in an album sync but in another album only one photo synced. Tried removing that album and re-syncing again, just one photo, the same one, appeared. So Finder seems to know what it likes and what it doesn't - which I find completely weird.

One improvement that Apple has made - which at least shows they are working on it - is the reappearance of the progress bar. When you click "Apply" the storage use bar to the left turns into a progress bar; so that at least is something.

As folk have pointed out earlier in the the old thread no-one at Apple pays much attention to the comments here so what we all must do is go to the feed back section and post as clearly as we can the problems we are still having. Contacting customer support will not help either as resolving this is beyond their ability as it is a operating system issue.

To cap it all off, since updating my iPad iOS to the latest version, I can no longer import my camera photos from the camera SD card.

Total disaster when this was working prior to the update.

Apple has lost my support and I am totally disillusioned by their failure to address an issue that has been around now since Catalina was released.

Back to the consultant again.

Not solved for me yet (at MacOS 10.15.4 and IOS 12.4.6 (iPhone 6)).

Won't sync Folders and won't even sync all my photos even when I select "sync all photos and albums".

(and no my iPhone's memory is not full)

:(

Working for me at the moment. Devices are: 2019 iMac 27, iPhone 6, iPhone X, old iPad Air, and 2018 iPad Pro. All devices and iMac are running latest software updates.

I've been following this discussion since the beginning of the original thread. I had a work-around using smart albums at the root level mirroring sub-folders from my original library structure which I'm unwilling to change. These were syncing fine on all my devices. I synced using a USB cable; wifi syncing did not work.

With the latest OS updates, I have had 100% luck syncing from the original sub-folders. No dupes, no black squares. Still using USB cable, have not tried wifi syncing yet.

I can't get to my photos on my Mac since the macOS Catalina update. The MacOS Catalina update is ridiculous for Mac users and photo app issues that come with it. They could do a better job communicating.

Got a call from apple customer care today because I also wrote in the yet closed thread that the problem is not solved and even worse for me. I missed the call but wrote a long reply to there support email that it is true: nested folders work.

I also mentioned the new progressions bar in the bottom of finder window which shows some syncing info.

But the sync process does not work at all. It stalls, after it looks like finished strange things happen in the background, and folders were added to the phone without status feedback. Even if the device was ejected it tells "syncing" in some folders but nothing happen. it took me 1 week, one whipping of the phone and 1000 of sync trials to get 90% from my former pics (around 30k) back to my phones, with duplicates missing folders, missing pictures, empty white "persons" frames outside the "persons" folder ... is a mess mess mess ... i would store all my data in a working cloud but have poor internet upload and after sync worked sends my first smartphone 20 years ago I do not accept this.

MusiaMat, I also noticed when syncing that it would stop and appear as though finished - the syncing progress circle had changed to the eject icon next to device, but not all folders had been downloaded (I was monitoring the Photos folders on my iPad). But the progress bar in the devices finder window was still grayed out and so was the rest of the download selection panel. After a short delay, syncing would continue and complete as expected. Is it possible that if you waited a bit longer that the syncing would complete??

Yes, you are right. I noticed this behavior since the first Catalaina release and it was impossible until now to understand when what happens. Last two weeks I tried really hard on several scenarios to figure out ... bye i am senior embedded system integrator for audio I have fun to waste weeks on finding causal behavior on malfunctioning systems

Hope you get lucky. I have spent countless hours on line to Apple support and sent numerous files, screenshots etc. which were then sent to the software engineers. There has been an update the Catalina and also iOS since then and still the issue has NOT been fixed.

Photos issues are obviously not a priority or they have messed up when they developed Catalina and now cannot find the bug that started all these discussions way back last September

Don’t hold your breath waiting for a fix

Patti wrote:

Who marks it "solved", an Apple representative to just some one like the rest of us having the same issue but something happened to work for them?

Only the user who originally started a thread can mark it Solved. In this case, the original poster (user dervatii) said "After almost 6 months this is finally solved." That tells me that his particular problem was solved for him.

I have had some of these problems since installing Catalina (I have an iPhone 6 and Apple TV 3). Can't sync any image in a Photo's Folder to my iPhone or Apple TV if I select individual Folders, or Albums in Folders. But if I select "Sync ALL Photos to iPhone" then almost all of my images sync to the iPhone BUT not quite all of them - Go Figure.

I have spoken to Apple Support (Australia) twice about this and both times they were helpful, investigated, confirmed the problems and said the problem was known and would be fixed.

The only thing I have to add to this long running mess is that Apple should be making a statement about current state of the problem, and issue a strong Apology when it is all fixed.

(I had initially thought that Apple Developers had deliberately left Folder syncing out of Catalina because they didn't have time to finish and test it, and that the normal old syncing would be implemented Real Soon in an update. Boy, was I wrong. Must be some almighty mess which is strange given that there were no major changes to Photos. Maybe, just maybe, there ARE major changes planned to Photos so why wast time fixing this %$%$#$ problem before the new release??? I'm probably being too generous?) ).

I would really like Apple to explain how a mess like this could occur, and what is being done to prevent it occurring again. I wrote computer software for 35 years and this problem is strange in the extreme.