Mac Os Catalina do not sync photos with iOS Devices

The right way is through the finder and then wait for Apple to come up with a solution to its sync problems. Until then, you will miss photos and some of the photos that do sync will look black on your device.

We have been waiting here for more than 7 months.

1) dont know

2 ) does not work ... added folder „Easter2029“ one week ago ... does not sync, does not even appear on the phone

So there is no correct way it simply does not work.

spent weeks on this since October

D6v1d,

To answer your question about corrupt photo files, here is my experience with two types of what I call file corruption:

a) I had photos that 1) would not sync, and 2) photos that sync’d as duplicates to my iDevices.  In order to fix this problem, I deleted those from my Photos library and re-imported them from my external hard drive where I keep backups of all my files (jpg and raw).  A re-sync eliminated the problem for those that were duplicates and those that would not sync. 

b) I had another subset of photos that would not sync.  But first, a little background….  I use Luminar 4 as an external editor for my RAW files.  I have it set up to be called via the extensions menu in Apple photos.  When I’ve completed editing in Luminar 4 and I save changes, it sends a new jpeg back to Apple photos along with all the RAW file edit commands to be stored with the RAW file and new jpeg thumbnail in the Photos library (see reference article below). Prior to the SUPPLEMENTAL update to MacOS 15.4, Photos would not recognize these new jpegs so they did not sync. After updating MacOS with the SUPPLEMENTAL update (released by Apple on April 8th), all new edits were recognized and would sync to my iDevices but not any of my previous Luminar edits.    I ended up having to go into Luminar and re-edit for each photo and have it send back a new jpeg to Photos.  For some reason, repair/rebuild of the Photos library does not fix this, only a re-edit in luminar would force Apple Photos to recognize the new jpeg.

Prior to updating PadOS /iOS to 13.4.1, there were lots of missing folders and missing pics after a sync.  But now after updating to 13.4.1 it works near flawlessly (see caveat below).  I noticed that for the first sync after updating the iOS, the photos folders on my iDevices were completely removed so the first sync was essentially a fresh start.  And it works.  All my selected folders sync over - 14,300 photos in 210 folders.  The only thing I’ve noticed is that there is this message “syncing…” at the bottom of approximately a dozen folders on my iDevices that doesn’t go away. Not sure why.  But, I can ignore that since ALL of my folders/photos that I’ve selected are syncing over.  I’m pretty happy with things now.  

Subsequent syncs?  No problem, no sync errors, no duplicates. Newly selected folders with photos all sync with success.  

Time duration?  It still takes the same amount of time to go through reading the photos database but copy time is dependent on how many additional photos are selected for sync.  I have about 50K pics in my Photos library so it takes a while to read through my database. 

In summary, you have to have installed the latest updates to MacOS and PadOS / iOS and delete / re-import any suspect photo files in your Photos library. Then it all works.

Here is a great article https://tidbits.com/2019/06/14/the-ins-and-outs-of-non-destructive-editing-in-photos-for-mac-and-ios/ written by Nik Bhatt on the inner workings of the Photos app.  Nik Bhatt is a former senior director of Engineering at Apple and led the Aperature and iPhoto engineering teams for several years.

Just a quick Summary:

Please be aware that although various suggested fixes have worked for some of us, they do NOT work for everyone.

Many Users of Photos still have major problems.

So DO backup your photos often, ensuring that you don't lose or overwrite old backups (these may be the only non corrupt ones you have!), and don't trust any fixes even IF they appear to work at first. The Photos library can still corrupt again later.

Still waiting on Apple to say something!

Fair point rodm7.

I went to the extent of restoring both my iPhone and iPad to ensure a clean sync after deleting and rebuilding my Photos app library. All photos were painstakingly re-imported and organized in folders. This was done in an effort to avoid any possibility of corruption. Well that didn’t happens. I’m still not able to sync my Photos app library to my devices using finder without the previously mentioned duplicate and missing photos. To add to the frustration the location data seems to have disappeared. When I click on that library in the Photos app it only show one photo despite all the photo files having the geotags. This is a mess and far from being resolved.

Frustrating you went thru all that for not - but I appreciate you letting us know. I will add that in my recent tests, after rebuilding and repairing Photos overnight and the couple of sync tests - I noticed that one smart album showing many blanks that initially seemed random but upon close inspection noticed that all the blanks happen to be the “hearted” Favorites assigned images - but oddly enough only blank on iPad, while on iPhone all looks just fine - meaning that album has no blanks on iPhone - so not sure that corrupt images are the issue, if that helps anyone. I tried removing the Favorites assigned keyword restarting iMac and removing the synced images from the iPad then assigning the Favorites again and syncing them again - not change - still blanks on iPad. Another 2 albums are both perfect on both devices. While another album missing 3 pics on iOS devices and not sure why they count is different from the count in Photos. Can’t tell which pics are missing, the album has many images. I am finding syncing to be taking about 35 minutes which is faster than previously versions of Catalina.

I have taken a few months away from this waiting for Apple to provide a full solution. Nothing.

I have over 50 albums and thought today would experiment. I synced 4 albums to my iPad and noticed only 1 of them won't sync. Most of the pictures appear black on the iPad. I decided to try that album on my iPhone. That sync'd fine. SO i decided to restore my Ipad back to brand new - and then synced the photo album. Same issue.

I think this confuses me even more as an Apple rep was telling me my photos library must be corrupt but surely this proves this not to be the case?

Has anyone done the Photos library repair? Any difference?

On April 13th I posted:

"I found a way to workaround the photo sync.

My hardware: MacBook pro Retina 2015, iPhone 6s, iPad pro 9.7" first generation plus my wife's iPhone 11 and iPad Air 2 2014. All of them with the recent OS updates.

Here my way to sync the Photos from my MacBook pro to the iPhones and iPads:

1st unselect Photos in the iCloud settings of all devices

2nd connect the iPhone/iPad via lightning cable with the Mac

3rd make a backup of the iPhone/iPad

4th in the Finder select all contents but photos to be synced

5th select the photos to be synced from the folder of the Mac (in my case the path is users/shared/data/photos1, photos2, photos 3. Each of these photos folders has several subfolders from 50 to 500.)

Important: Stay on the Photos page of the sync tool!

6th click on "apply".

7th if there is an error message like "folder 'unknown' not found" select the folder on the Mac again and click on "apply" or "sync", whatever is offered.

8th if it is still not syncing or even deleting your photos from the iPhone/iPad repeat step 7th.

This worked for all my devices. The only problem: I have to run one more sync for the music.

Next I tried it with my new iPad pro 11" 2020 and it's working as well.

Next experiments I did: Syncing with Win 10 based iTunes.

I tried it using BootCamp, but unfortunately this doesn't give acces to the Mac partition.

Next I tried Win10 with Parallels on my Mac. This doesn't work as well. iTunes crashes after some minutes.

Perhaps I will try Win 10 with VMWare and Virtual Box as well.

Finally I want to say, that Apple was an excellent example for reliable Hardware and software as well. This was their big advantage over the competitors and this was the reason for the relatively high prices they could charge from the customers."

I am going to ring Apple again and speak to a senior advisor. Photos were syncing correctly in my phone and just plugged it in and synced and loads have been removed from various folders so photo count is different across all albums on phone versus Mac photos!!! Copy and paste into new folders still doesn’t recognise once pasted on Mac photos so u end up doubling up. Modified photos come out as white no picture when syncing so not recognised on phone but yet showing on Mac photos!

What is wrong with these developers how can they get this so wrong, it wasn’t broken why didn’t they just leave it. Absolutely appalling from Apple.

I am now noting that my iPhone syncs fine.

However my iPad does not.

I am not sure if this is good or just bad as inconsistent. I have tried resetting the iPad and still some albums just have 80% blank (black) images. The exact same albums are fine on iPhone.

I finally gave up. Effective 4/21, Microsoft gave everyone with a subscription 1TB of free space on OneDrive. I exported all of my files from Photos and uploaded them there. It took no time to remap things to albums. I'm finally free. 40,000 files, and everything loads perfectly on my phone now. Unfortunate solution, but if Apple cannot get their act together to fix their own software, they're going to lose people. Forcing people to use iCloud is a losing business model.

Oddly my iPhone XR loaded all pictures just fine using the latest updates on both my MacBook & XR. I loaded my iPad Pro from Mojave loaded on my spare MacBook just as a comparison, nothing to choose between them other than the changes to iTunes.

Thanks to all for testing,..,.but I have not tried any of the suggestions here waiting for at least several people to confirm whether any of them work. After the last update, we were able to to sync albums that were missing since Catalina and IOS 13, but the workaround we used to sync photos is no longer working: In order to avoid duplicates, we were deleting all photos first. This would take a couple of tries for complete photo removal. Then we would sync. It would take a while but it somehow worked. Now, I can’t remove all the photos. And when I sync to add new photos, theduplication of photos appear again, now with empty black boxes to signify a photo. However, when I look at the photos that were synced in the albums view it all appears without duplicates and without the black boxes.

It seems every one’s experience is slightly different but generally filled with bugs. Im hoping for a solution soon as this has seriously changed my mind about this expensive phone we purchase every several years.

I too have been reading everyone's experiences with different scenarios but all around the same theme. I'm still waiting on Apple to come up with the fix. I read where someone had some luck after the supplemental update of 10.5.4 and wanted to try it. I could not find the Supplemental update for my Late 2015 iMac as it said that I was up to date.(?). In their infinite wisdom, they did not notate the supplemental with a different release number. Poor software development! I'm a retired project manager of software development and Apple has shown that their development lifecycle process is in need of major improvements. Tim Cook said that this was going to improve after the Catalina fiasco. Let's hope so.

If you're coming here because your iOS device (in my case, an iPhone 7) wasn't syncing photos and your Mac (Catalina 10.15.4) Finder window wasn't showing any folders under the Photos tab (even though you know the Photos app has many folders in it), what worked for me was to unplug my phone and plug in a different iOS device (in my case, a 7th-generation iPad).

The Finder window then correctly displayed the expected folders under the Photos tab. (The iPad also synced automatically, although I don't know if that setting has anything to do with this "fix"). After I unplugged the iPad and then plugged the iPhone back in, the expected folders showed up again under the Photos tab for that device and I was able to sync them successfully.

As to why this worked, your guess is as good as mine.