Mac Os Catalina do 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; 4th generation 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

Copperlanding

Hi - FWIW, if you read the first post in this thread, the OP intended this thread to be for people who DO use the Photos app to sync. Most of the people posting here do use it.

If you want to read about experiences NOT using the Photos app to sync, please see these two threads (and I'm sure there are more)! Good luck.

https://discussions.apple.com/thread/250716061

https://discussions.apple.com/thread/250927454

So basically are you suggesting that we should be quiet, polite and don't complain about a huge problem that a lot of people are experiencing?

Show me where I said or implied this?

I am merely pointing out that no amount of threatening, stamping of feet or calling out Apple will change the purpose and function of this community.

I found very rude and wrong that nobody "official" from Apple is participating to this forum, especially on hot topic like this.

Tell them how you feel.

Feedback for Apple goes here >>> http://www.apple.com/feedback/

You agreed to terms to be here, and Apple clearly stated in those terms they do not necessarily provide support here. "They" are here to preserve the peace, but not speak to an individual ongoing issue such as this.

That 100s, 1000s or even 10s of thousands are affected does not change this. Not my rule.

Yes, this has been my routine to sync as well. This week I tested adding a few photos and syncing as before IOS 13/ Catalina and the result was unfortunately the same. During the syncing process, I can observe the photo count on my iphone. First, a percentage of the photos are removed, then the photos start to be added. Eventually, the count of photos added surpass the number you can observe on the finder as the total number of actual photos that the sync will produce. This sync produced many duplicate photos in the “curated” view of photos and also in the albums section of photos.

It looks like we have to continue to spend several hours everytime we have to sync. Apple should add that to their step by step guide to syncing using USB cable via finder....on this help page of theirs: https://support.apple.com/en-us/HT210611

I do not know if my photos library is corrupted. All devices and mac are less than a year old. I have also read the many recommendations from several posts here on sucessful syncs but have yet to hear from other users to confirm this.

Hello everyone. I’ve been following this discussion since last autumn because I had the same problem. In October I created a discussion that focused on one aspect: During each sync after any changes, every single photo was removed from all my iOS devices and then all photos were reinstalled. It caused numerous duplicates and the photo count and storage used were erratic.

It’s not exactly what some of you are saying, but it’s certainly related. Here is the link to my original discussion: https://discussions.apple.com/thread/250777933

I know you won’t be happy about this, but before my three-month trip to Asia I decided I couldn’t deal with this anymore. I bit the bullet and began to pay 99¢ per month for iCloud storage. For only a dollar a month everything has been working absolutely perfectly because since switching to iCloud Photos. For many years I preferred the syncing method but now because of iCloud (rather than syncing) I’m not stressed by Apple ignoring the syncing problem.

Yes there was a learning curve but in the end I’m happy with my decision. However this in no way explains why, over the past nine months, Apple can’t or won’t solve the syncing issue.

I actually managed to sync some photos from folders under Pictures ( I too have a folder for each year and then a subfolder for each month). I have had this setup and have always managed to sync it over to my iphone (except that all subfolders were not showing - so all images for all months were just showing together under e.g. 2014).

Not being able to sync any of the folders with a new iPhone 11 Pro and IOS 13, I suddenly managed to get some of them to sync (didn't want to select all 30 years, so started with 5). Not sure whether this is what made it work, but these were the steps:

• create a new admin user
• logged out of main user
• logged in with new user and connected the phone without syncing anything
• logged back into main user and then it worked

BAD news is that after syncing like have my photos 3-4 years at a time, it stopped working again. Now the wheel just keeps spinning.

But my point is that it can work and I have managed to sync like 7000 photos from folders under Pictures onto my iPhone.

Seems a bit temperamental, but not entirely impossible.

As promised, my status update.

The past 2 days I spent several hours with an Apple Support engineer on the phone.

He confirmed, that there any man complaints about this and Catalina in general.

The sync issue is escalated to engineering.

What we have tested and the outcome:

Pictures which are in folders are not synchronised at all.

Pictures which are in an Album directly under My Albums are synchronised depending on their size

1. 6 pictures which were each between 2.4MB and 3.2MB were not synced
2. the same pictures each between 297KB and 440KB were not synced
3. the same pictures each between 13KB and 18KB were synced

When I tried the 1. group of pictures directly from the Folder on the Hard drive (i.e Select "Choose Folders" instead of "Photos" in Finder) it worked fine.

Logfiles and system data have been captured and sent to Apple.

Response time is about one week.

I will report back once I receive the feedback

Have a nice weekend!

Here is a temporary workaround which is far from perfect but is working for me.

• Create a new folder on your desktop and name it whatever you like. I named mine Temp Photo.
• Open Photos app on computer.
• Drag each folder you want synced from My Albums to the folder you created on your desktop. This duplicates all those photos so make sure you have enough space.
• Move that folder wherever you like.
• Connect phone and go to Photos tab.
• Uncheck 'Sync photos to your device from' and select Remove, then Apply. Once that sync finished, I power cycled my computer and phone. That may be unnecessary, but it's what I did.
• Back in the photos tab, check the 'Sync photos to your device from' box and select the folder you created.
• Make sure Sync 'all folders' is selected and Apply.

That got all my photos back on my phone while I wait for a fix.

The next problem is when I try to send any of those photos from my phone, it crashes back to the home screen.

The fix I found for that is I open the photo I want to send in Snapseed (I'm sure any photo editing app will do) and export it to my camera roll, then send it from there.

Like I said, it's a far from perfect workaround but better than nothing. I hope this helps someone.

I too am considering switching to a PC, and that's a real stretch for me. Catalina is a POS. Here are just a few of the "features" I am having some fun with:

1. Pic sync...very frustrating
2. Sssslow. Not sure what happened but it takes a long time for my mail app to open, not to mention Music and photo apps
3. Music...where's the remote option that iTunes had?
4. system preferences...probably a photo app problem too...hard to get a screen saver working that uses any of my pics
5. This new operating system does not run many of the programs I paid for...Office for example, Aperture, my scanner, and many more. And even when I update the software and firmware for my scanner...it doesn't work
6. I have had to reboot my iMac almost every time i leave it on for any length of time and then Music and Photos both take forever to open

What drew me to Apple in the first place was the integration tweet devices and the way it handles audio and pictures. if all those cool abilities are now gone, it's time for a change.

Suggestion...give us an easy way to go back to High Sierra, where everything worked or fix the **** thing before I buy a PC

Same problem. Spent nearly 2 weeks trying to solve this issue with Apple support

• I've started a new Library and added some photos - nothing
• I've uploaded my entire album to iCloud and re-downloaded it to a new album - nothing
• I've started a new login, copied my Library over and tried to sync them there - nothing
• I've also started a new library in the new login - nothing
• If I put an album by itself with no folders, it works fine, but if I have an album, within a folder - nothing

Another process that worked if I select “All photos and albums”, but it won’t work when I select “Selected albums”

A further update...

Fingers crossed mine SEEMS to be syncing for now, here are a few notes I hope will help someone:

• I'm suspicious that alternating between USB and WiFi for the same device perhaps causes problems.
• I ran a repair on my Photos library.
• I deselected all albums in Finder sync, emptied the device and then added them
• The finder sync pie-charts MAY operate as follows: First=Backup, Subsequent=Sync stages, Last=waiting for items to copy
• Even when adding a single photo to a single album, the sync process seems to touch all albums and during the sync the numbers of photos in untouched albums varies, coming to rest at the correct number ony after the sync is finished.

CB

My experience to date:

1. "Sync photos to your device from -> Photos" on my iMac will sync albums nested in folders to my iPhone and iPad only if I select "Sync -> All photos and albums" instead of my preferred option to "Sync -> Selected albums". However 1,648 of my 26,317 images in my iMac Photos library do not sync to either of my iOS devices. I have not been able to find a fix for this. I tried removing all photos from my iOS devices and syncing again but it made no difference. I also tried repairing my Photos library on my iMac but that did not make any difference either. It looks like the same 1,648 images in my iMac Photos library do not sync to my iOS devices no matter what I try. Very disappointing and frustrating.
2. Home Sharing "Share Photos from -> Photos" on my iMac will share albums nested in folders to my Apple TV 4K only if I select "Share -> All photos and albums" instead of my preferred option to "Share -> Selected albums". All 26,317 images in my iMac Photos library are shared with my Apple TV 4K, although I would prefer to only share selected albums. At least I don't have the missing photos problem that I have with my iOS devices.

This seems to be a problem with Catalina. I hope Apple is aware of this and will have a fix in the next update.

After grappling with this issue for some time and not yet finding a resolution, I thought I’d summarise my observations:

• The problem existed in Mojave. I first noticed after updating my iPad and iPhone to iOS 13 that the sync process no longer skipped unchanged albums, but seemed to take ages and interfere with everything, leading to the symptoms described below.
• It isn’t limited to albums within folders. My top level albums do not sync properly.
• As pointed out by a couple of other folk, the usual failure symptoms I see are some duplicate photos, where one of each pair has location info and the other doesn’t.
• The only way I have found to recover the situation is to deselect albums to sync and then reselect. Or to globally deselect syncing of photos and re-enable.
• The latter only works reliably with my iPad, not my iPhone. This evidence may be invalid due to a small sample of tests, or it may point to logic which differs between iOS and iPadOS. Or it may be due to a performance-related race condition in the logic. My iPad Pro takes significantly less time to sync (well or badly) than my iPhone X.
• The Finder pie charts seem to relate to the sync stages previously elaborated in iTunes - Backup, Syncing Content, following on after each other without being labelled.
• A repair of the MacOS Photos library didn’t help.
• The Finder sync panel can sometimes forget state, requiring a MacOS restart or Finder relaunch. Sometimes an iOS device reset is also required.
• The whole process is unreliable regardless of WiFi or USB connectivity for sync.
• It would be great (even as a workaround) to be able to retain certain albums on the iOS devices whilst excluding them from the sync process - it’s annoying that multiple albums get corrupted and need to be restored after virtually every sync.
• Regarding the sync process ‘interfering’ with all albums regardless of whether their contents have changed - I wonder if this could perhaps be due to logic which trawls for the purpose of face recognition or similar...

In short, very frustrating and time consuming. Not rocket surgery in this day and age. Should be the sort of core bread and butter functionality that is included in Apple’s regression testing. I do think it will be fixed, but it really should never have been broken in the first place.

What on earth were Apple thinking when faced with the strategic need to rehome the sync process from iTunes to Finder? The sensible engineer would have surely thought... “Syncing logic is complex. Let’s make the first step to retain the well-tested logic and constrain changes to the user interface only.”

CB

Interesting article Patti.

Catalina's drop of 32 bit support caused me to:

• ditch MS Office in favour of Pages, Numbers and Keynote - which seem fine for my purposes actually
• rewrite a piece of 32-bit music software (MIDI Patchbay) to operate in the 64-bit OS; luckily I was able to find the decade-old source code in GitHub, and luckily I'm okay with writing software!

On this issue of ours - I'm wondering if MacRumors would take the story. It's the kind of stuff they do comment on and may gain a groundswell of support from users who don't use this forum. Just a thought.

CB

Waiting for Apple to fix, I’m proceeding like this: 

1. Duplicate the nested albums I want to be sync’d and move the doubles under the root directory
2. Flag only those albums and synchronise the device, by pressing the “apply” button first, and then again the “synchronize” button. Sometimes I’ve had to repeat these steps two or three times, but eventually it worked.

In case Apple fixes the issue, I’ll only have to delete the duplicated albums.

Of course I’ve always kept a copy of my pictures out of Photo app