Mac Os Catalina do not sync photos with iOS Devices

I have a macbook pro (2014), newest Ipad air and iPhone 8, No Icloud, but I use shared albums and photo stream. Apple Photo's is 64 GB big and contains over 35.000 photos and 3.000 video's. My entire photo library has my directory structure. I have the same problem. No synchronization between photo library and numerous IOS devices.

I have tried the following things and came to the following conclusions:

• Put photo albums in root folder of Photos-app. - This results in a partial sync of that particular folder. When syncing iPad or iPhone the exact same photo's and amount of photo's get synced. Never a complete sync.
• When syncing a direct folder from the HD and bypassing Apple Photo's, all documents in this folder get synced correctly. photos and films.
• I have created a new Photo-database in the Photo-app. I let Photo's manage the folder structure. And i did not experience any synchronization issues.
• Only Smart albums get synced. Regular albums in the root do not get synced.
• I get the same behavior or problem when syncing iPad or iPhone.
• I see no progress bar or something when syncing iPad or iPhone.
• Syncing a direct file works (syncing a single movie to AVplayerHD).
• Syncing via Wi-Fi does not work

This gives me the impression that something is wrong Photo's, not my devices or cables.

I am currently thinking about purchasing a new Macbook Pro but these issues are putting a dent in the Apple-trust I have. :-(

Catalina is a disaster, iOS13 is also a disaster.

• The PhotosApp do not sync properly
• Some images within the PhotosApp duplicate while syncing
• Some music syncs, some does not
• Bluetooth mouse constantly disconnects from my Mac
• As far as "sub folders" are not allowed, I'm a firm believer in tech adapts to us, we do not adapt to tech

I too have been old by Apple Techs that "they are aware of the issue and a fix is imminent". Which of course we know really means nothing as many on this board have been told the opposite.

For my photography, I'll be moving away from Apple and brining my 30k+ images to my Synology server. Images will no longer be on my iPhone or iPad, but they will be in the folder structure I deem appropriate, not a tech company's idea of what is best.

Sadly, Apple has lost its way, its creative edge for creative professionals, you know, the people that put Apple on the map.

We can only hope that one day all of these bugs will be fixed, but until then, hello Synology!

Hello captainharry,

• If you can, please see my post below as it may help you.
• Your structure is the exact way that I have mine and how it dod work (for me) prior to Catalina/iOS13/
• It would seem that others in this thread were not so lucks and their syncing was broken before Catalina.
• In my opinion, I think if you attempt to do it in this manner you'll run into technical issues (but again, others have not), so I would proceed with caution.
• Good Luck!
• 
  

My recent sync tests between my iMac and iPad Pro and iPhone 11 Pro (tested in macOS Catalina 10.15.1 and the most recent update 10.15.2 (as well as prior and the most current updates to iOS and iPadOS).

1. Along with most people in this forum I have not been able to sync Albums in Folders via Finder since Catalina.
2. I recently tested a couple of smart albums placed directly under My Albums and while the album synced perfectly on my iPhone, unfortunately most of the images on my iPad are blank/black boxes - over 95% are black - and I tried multiple syncs and restarts and same result. I eventually stopped syncing that smart album and tried a different smart album with fewer pics & vids and that album has many blank black boxes where pics or vids should be on my iPad - but about 75% are visible on iPad. Not sure why my iPad Pro is having issues while my iPhone is not.
3. I did not have any syncing issues before Catalina.
4. My photo library is too large for iCloud so that is not an option, otherwise I would attempt that just to circumvent this issue and not have to wait for the software fix.

My workaround works reliably and gets all my photos onto my devices. It's simple and not particularly efficient, but it works.

NOTE: that I only transfer smart albums (one per year), directly under "My Albums".

• Use USB and not wireless (for performance reasons)
• Have Finder configured to disable automatic sync when device is connected
• Go to the photos tab and uncheck the checkbox against all albums
• Apply and allow the albums to disappear from the device (apart from the initial backup, this doesn't take long)
• Re-check all album checkboxes
• Apply and wait until all the albums reappear on the device (it takes perhaps an hour for my 10,000 photos)

As I said, my particular syncing issue is about top-level smart albums gaining random duplicates of many photos with each sync - including albums which should remain untouched between syncs. This may not help in your particular cases.

CB

From other replies in this thread I have used a "successful" workaround for this issue.

The problem is folder structure.

No folder or its contents under My Albums is transferred.

The solution is to move only the album to the top level (root) of My Albums.

In Photos on your Mac,

• move the Album you wish to move to the iPad to the root of My Albums
• syncing within the new Catalina Finder window will then work.

Not ideal (AT ALL) in preserving YEARS of organizing and curating structure and selects, but a solution to at least get several albums onto the device for a temporary project.

What can be done is duplicate the album in its location in your structure, then move the duplicate to the root of My Albums to be deleted later once Apple gets the fix done.

Best for a New Year ya'll.

@quiksilverboy - just ref your last point, I can confirm that the sync problem exists with smart albums.

i’ve never used folders.

i selectively sync via USB, smart albums only (each 1 year, based on date range) and these albums are directly under My Albums.

Since iOS13 with Mojave, the sync problems began for me.

Then with Catalina, things became worse, and with Finder, more difficult to troubleshoot.

The problems I refer to are:

• Sync taking ages due, it seems, to unnecessary processing of content which is unchanged since previous sync
• Occasional blank pics on iOS device
• Duplicates (seemingly randomly) on iOS device after second sync and further syncs

My workaround is to sync less often and to deselect all albums, deleting all pics from device with first sync, then select all albums and sync once more. It takes a while.

CB

I am suffering from this issue as well - none of my Albums are syncing to iPhone, iPad or Apple TV.

Here are some updates/tips:

1. I've filed a bug report using Feedback Assistant right after Catalina launched which is still open and resolved.
2. I've also been in contact with a Senior Adviser since early December. We did some troubleshooting to confirm the issue initially. I reached out to him after Catalina 10.15.3 and iOS 13.3.1 were released and still didn't fix the issue. He assured me that it's a known issue that is still being worked on. While that might be true, it certainly seems that this is not a high priority issue for Apple to fix. Makes you wonder if any of the programmers working on these areas actually use their own software...
3. I tried moving all my Albums in Photos under the main 'My Albums' and while that actually syncs the albums, it only syncs smaller photos (seemingly up to 1280 pixels wide), so that's not a viable workaround for me.
4. Syncing using a Smart Album doesn't work either, it only syncs smaller photos (seeemingly up to 1280 pixels wide), so that's not a viable workaround for me.
5. Since I have my photos stored in a folder and imported them into Photos as referenced files, I was looking at the option of syncing from a Folder instead, but that's also not a viable option for me as it works fine on the first sync and then on subsequent syncs it creates duplicates after duplicates.
6. Switching to iCloud Photos is also not an option for me as it only works for photos that are moved into the Photo library - it does not work with referenced files. I am using referenced files since I do all my actual photo editing in Photoshop and Lightroom.

I did find an alternative workaround that at least partially gives me what I am after: Shared Albums

I turned on "Shared Albums" in Photos, on iPhone, iPad and Apple TV. I then created a shared album in Photos and added all the photos I want to sync to it. That way, I can view all the photos on my devices and on Apple TV I can also select a shared album as a screensaver source which is something that we are heavily using at home.

It's not ideal as there is no folder structure and none of the standard Photos features work for shared albums, eg. no searching, no people detection, etc., but at least I can view and show photos again.

On the plus side, it made it a lot easier to get the photos onto my wife's iPhone. And Shared folders don't count against your iCloud storage, so no need to spend any extra money.

I still hope that Apple fix the actual issue soon, but at least for me this works for now.

We'll, I have also the syncing problem like all of you. I've got a temporary solution to keep my Photo library synchronized without duplicates or errors, but it can be synched only once; in order to add new pictures to the library I have to do the complete process again.

• First of all, prepare the photo library on the Mac. In case you want to copy and organize your iPhone/iPad pictures to the library, manage albums, etc... now it's a the right moment.
• On the Mac Photos app, create an album called "Empty" which is (surprise!) totally empty.
• Sync the iPhone or iPad and on the Photos section, choose to sync ONLY this "Empty" album.
• This should delete the synched pictures (which contain errors) on the device. Check that the sync was completed correctly. The recent pictures stored on your iPhone will remain safe, don't worry about them :)
• Repair the Mac Photo library: open the Photos app while holding down the Option and Command keys. Click Repair.
• Now it's probably a good time to restart the Mac and the device, but I'm not sure it's necessary.
• After that, synchronize your device with the Mac, selecting the Albums you want to synchronize, or the full library.

After the process, the Albums I synchronized were done correctly on both my iPad and iPhone. If I do add new Music or Books to the Mac and the Photo library remains unchanged, the sync will be correctly done. If I change something on the Photo library, (add pictures or albums) I get errors again.

Now I can patiently wait until an update comes and things work again correctly </ironic mode off>. Hope they fix this issue, and still can't understand why is not already fixed. It worked out just fine before the last major update, please, just restore the old algorithms!!!

<old guy mode on> This situation remains me to the time I used windows 95, 98 and XP before switching to my first Mac, when many tricks and research was needed to get basic system functions to work just correctly. After switching to Mac, almost everything worked just as expected, that was the almost magic and great thing about MacOS. Unfortunately, not anymore.

Sadly I have given up hope and moved to another photography platform.

• Apple has forgotten us
• They have put out the worst OS since the introduction of OSx
• Catalina is an unmitigated disaster in every sense of the word
  • I have moved back to OS 10.14.6 but sadly since the Photos app had been updated for Catalina, there is no going backwards, which is why I have abandoned Photos and moved along
• I should not have to figure out the technology, it should work the way we work
• iPhone & iPad is still awesome, but Apple has neglected and forgotten about the very users (like me) who helped make them the creative force they used to be. My entire agency runs on Apple and we are all back on 10.14.6 so the machines will actually run and we can actually make a living

Sad to see what is happening.

I see that Apple has marked this thread as "Solved". No, it is not solved yet!

Yes, after the upgrade of both iOS and MacOS, the photos started syncing again.

However:

1. the random "black blank squares" are still appearing in many albums on the iPhone. When you tap into this black squares, there is a no photo but just the geo-tagged photo location displayed at the top. Adjacent to it is the actual photo but without the geo-tagged location.
2. On the iPhone, many albums are still showing "Sycning..." at the bottom even though sync has finished more than 12 hours ago.
3. Some old People names whom I do not want to see and deleted in MacOS Photos are still showing up in iOS.

It is really buggy. Please help to really fix it!

Adding some of my same & similar issues as below. Which I'm using iPhone 7 in iOS 13.4

1. Some old People names whom I do not want to see and deleted in MacOS Photos are still showing up in iOS.
2. Lots of duplicate photos in the albums

And issues in iPad Pro in iOS 13.4

1. Some duplicate photos in the albums as well
2. Erased all the photos after updated the iOS

Hi MikeyB,

thanks for the Post.

Could you please explain a couple of things:

• What does "Fully" repaired mean? Photos has only one option for Repairing a suspect Photo's Library as far as I'm aware (a very simple double click on the Photos App while holding down Option + Command keys). Did the Apple engineer guide you through some special repair process?
• What did a Safe Mode boot have to do with all this:
  • You can ONLY sync Photos successfully now in Safe Mode?
  • You performed the repair in Safe Mode?
  • The Safe Mode was a once only thing (for some unknown "engineer" reason) and a Photos sync now works in normal bootup?

Thanks mate.

This references help/comments from MikeyBananas and gvd1. Thanks guys.

Just adding two paragraphs from my experience:

(1) Have had major problems syncing images from iMac (2017) to iPhone 6, from Folders in Photos as well as other minor syncing probs. with Catalina. Solved for now (hopefully).

Tried the suggestions from MikeyBananas and, unlike many Users, had reasonable success.

That is, I did a Repair in Photos on the Library (took about 2 hour for 16,000 images just so you know. Seemed stuck on 74% Restoring but eventually reached 100% complete). Rebooted in Safe Mode, as per Mikey's suggestion (dunno why this would help), and then rebooted normally.

Synced a few Folders in my Photos Library to iPhone. Successful (first time Folders have synced for me).

Synced a few more Folders. Successful except a few Albums on my iPhone had a few missing images.

Manually selected ALL my Folders and other Albums in my Library and synced then to my iPhone. Total success. All images on my iPhone.

Obviously still not ideal (as multiple Syncs were needed), and may still fail on the next Sync.

(And I know the steps above don't work for everyone because of reasons below???)

(2) An educated guess as to what is going wrong...

Several facts stand out:

1. many different types of problems reported since Catalina:
   1. can’t sync any images in Photos' Folders.
   2. some corruption of some images.
   3. a Sync All sometimes syncs images in Folders but not all images.
   4. results and bugs vary from one sync to the next, and one User to the next.
   5. Just one of my (many) problems: Albums created on my iPhone by syncing from Photos on my iMac show a certain no. of images in an Album which is actually wrong (i.e. the no. of images shown at the bottom is say “21 photos” but there are actually 50 healthy images displayable in that Album on my iPhone. What?).
   6. etc. etc. etc. and etc.
2. a Photos Library Repair (plus a reboot in Safe Mode once only - seems to help?) only fixes the problems temporarily for most people.
3. Apple S/W Engineers are having a devil of a time finding and fixing this problem.

My educated guess (from 35 years experience writing and debugging S/W) is that:

1. Catalina introduced:
   1. a bug in Photos that corrupts the Photos Library (but in random ways for different Users since every Library will be different in some manner),
   2. OR, some direct corruption of the Library happened (during the actual Install of Catalina)
   3. OR, both of the above.
2. AND, the Library Repair process does not fully remove the corruption (maybe it removes it completely for a few lucky Users but leaves minor corruption for most as it is a new bug that the Repair process simply doesn’t yet know about), and that subsequent Syncing (to iPhones, AppleTV etc.) fail from the remaining minor corruption, and/or the continued use of Photos and Syncing on a corrupt Library makes the corruption worse and worse (until a Library Repair partially removes the corruption). Then repeat all of the above over and over.

The above fits the facts, and I can’t think of anything else that fits all the reported facts.

So:

1. have any Users restored a preCatalina Photos Library from backup and found whether this eventually corrupts or found that it never does? (I haven’t tried this yet).
2. has Apple explored comparing a Catalina Library with the exact same one backed up before Catalina was installed, to see what the differences are? Then doing a (hopefully) unsuccessful Sync and then comparing the Library after the sync with the one before the Sync, to see what the difference are? If there are differences then THAT is related to the corruption point.

Well that's my rave done. Good luck everyone until Apple actually solves this mess. Oh, good luck Apple.

For gvd1 and others using Photos and having Syncing probs.....

(just a first word: before experimenting please backup your entire Library even if it appears to be corrupt, or risk losing everything. Then backup again. On a different medium).

Just old and new random musings given my 35 years experience writing and debugging S/W:

1. (just a repeat for new readers): a few of us have had success with MikeyBananas and gvd1 suggestion: Boot up in Safe Mode and do a Repair on your Photos Library. This helped a few of us even before this week's Catalina Supplemental update.
2. if your Library is not too big, export all the images to hard drive (careful to maintain Quality), delete the Library, create a new Library with whatever Folder / Album structure you want (but no images) and import the images into the new Library. I would import only about 20% of the total images at a time, then do a test Sync - then repeat. Maybe without Folders initially - add Folders later if you want. If my wild guess about Catalina corruption of the Library is correct then this might be the only way to remove the corruption. A painful time consuming fix of course. (There are Apple Scripts that do this for you but also a pain if you are not expert at coding/modifying these scripts).
3. do multiple Library Repairs in a row without doing any Syncing in between (in Safe Mode?). Maybe 4-5 Repairs then try a Sync. My logic here is that the Repair process hasn't yet been updated by Apple to handle (fix) a new form of corruption. Running it multiple times might (?) clean it out "in bits" (this has worked with Hard Disk repairs).
4. have any Users restored a healthy preCatalina Photos Library from backup and found whether this eventually corrupts or found that it never does? If it stays healthy then any new (missing) images only in your corrupt Library could be imported into the restored healthy Library. (I haven’t tried this yet).
5. has Apple explored comparing a Catalina Library with the exact same one backed up before Catalina was installed, to see what the differences are? Then doing a (hopefully) unsuccessful Sync and then comparing the Library after the sync with the one before the Sync, to see what the difference are? If there are differences then THAT is related to the corruption point.

I probably won't test any of the above real soon. My Syncing is now working again, and it's not that I don't care, I'm just busy else where currently. But if any Users are desperate to fix this problem right now then try the suggestions and let us (and hence Apple) know the results. I could say Good Luck but that doesn't seem to help.