Mac Os Catalina do not sync photos with iOS Devices

I had the same issue, and if I ticked a box in any of the tabs to select a Photos album to sync or to modify an option, I could't even push the apply button because it was greyed out.

Then I read a comment on Reddit suggesting to untick all the sync checkboxes at the top of each tab and then push the sync button next to the storage bar at the bottom.

After the sync finished, I was able to tick back on my Photos sync, choose the albums I wanted to sync and finally apply the changes with all my Photos album back on my iPhone X.

Hope it helps.

Cheers

So, I've had the same issue with my iPhone X (iOS 13.2) and my MacBook (MacOS 10.15). Until I installed MacOS 10.15.1, I was NOT able to get my albums in folders (by years) to sync. I have been noticing that it takes forever for my iPhone to sync and there really ins't any visual clues in the new OS. But, as an experiment, I had an album NOT in a folder, but directly under the My Albums folder. IT WORKED! I was able to sync the album to my iPhone. So I tried all my other ablums (both Smart Albums and regular type albums by moving them into the My Albums folder. They all sync'ed. I'm fine with this, I can rename the albums to show the year as long as I can manipulate my picture library on my MacBook. It is not perfect, but it works for me.

The icon of the empty circle fractionally getting filled caught my eye. The two arrows chasing each other in a circle is misleading. The empty circle appears to indicate that something useful is happening.

I will be happier when folders can be used again, but I sigh with relief that albums are sync'ing again.

I have been in contact with high level support on the issue over the last few weeks. They have taken screenshots and diagnostic files from me and a few days ago admitted that the issue has now been recognised by the software engineers to be a bug ( I think we could have told them that ages ago but .... ) and a fix is being worked on for a future update to Catalina ( timing of course TBC )

Complaining about the bug in this forum will not have any impact as Apple does not monitor/take any notice of posts here ( this was specifically stated as part of my discussions with them ) so the only way to keep pressure on them and to keep it high priority is to :-

1) call up Apple support to report the issue. Note to say the issue is about direct syncing via usb/wifi using the new Finder process and albums within folders not syncing and NOT Cloud syncing as that is a separate issue.

and ...

2) if you do have the issue above, report a bug on Catalina AND on Photos with Apple on the following sites

https://www.apple.com/feedback/macos.html

and

https://www.apple.com/feedback/photos.html

again being specific about the selective sync via Finder and albums within folders not working

Keep the pressure on and hope for a speedy resolution.

Ok so im no a big Mac guy. I just recently bought my 1st Mac but have owned a iPhone since the start. I was experiencing the same issue with my photos. I was messing around earlier and figured out a way to get my photos synced with my iPhone from my Mac. I had my photos in individual folders with the album inside of of the folder. I opened the folder and left clicked on the album and dragged it out of the folder into the column that the folders are in and dropped it there. I then checked the box beside it and was able to sync it to my iPhone then. Well i hope this helps with the problem for everyone

Yes, there seems to be a lot of confusion now in this thread.

The original issue is Photo "ALBUMS" located within "FOLDERS" on macOS Catalina Photos.app (and perhaps Mojave?), not syncing with iOS devices using a USB Cable (or perhaps WiFi aswell). - Via Finder.app (Not iCloud)

I so far have tested Catalina 10.15.0, 10.15.1, 10.15.2 (most recent developer Beta) in conjunction with iOS 13.3 (Developer version) and this does not work.

Some people have suggested dragging the ALBUMS outside of the Folders directly under the built-in "My Albums" level. I think its fair to say most of us have had success with syncing albums when we do this step however, for me, its a total mess and looks very unorganised in Photos.app on Catalina.

So, i have reported the issue several times using the online feedback forms., If this is not resolved this week i will start calling. I just don't have the time during the week to spend hours on the phone with them over something i know will not be resolved by the person troubleshooting. In my opinion, this is something the software "engineers" have to fix.. getting their attention is near impossible. Unless someone knows a tech YouTuber who will have contacts? lol

So, knowing that 10.15.2 will probably not fix this issue, my temporary workaround is to create a Smart Album called "iOS Sync" at the root level of the Albums folder, and use a bunch of "Album is ..." conditions to add all the albums I want to sync. Seems to work, but a total pain in the *** to set up :/

I have been in contact with high level support on the issue over the last few weeks. They have taken screenshots and diagnostic files from me and admitted that the issue has now been recognised by the software engineers to be a bug ( I think we could have told them that ages ago but .... ) and a fix is being worked on for a future update to Catalina ( timing of course TBC )

Complaining about the bug in this forum will not have any impact as Apple does not monitor/take any notice of posts here ( this was specifically stated as part of my discussions with them ) so the only way to keep pressure on them and to keep it high priority is to :-

1) call up Apple support to report the issue. Note to say the issue is about direct syncing via usb/wifi using the new Finder process and albums within folders not syncing and NOT Cloud syncing as that is a separate issue.

and ...

2) if you do have the issue above, report a bug on BOTH Catalina AND on Photos with Apple on the following sites

https://www.apple.com/feedback/macos.html

and

https://www.apple.com/feedback/photos.html

again being specific about the selective sync via Finder and albums within folders not working

Keep the pressure on and hope for a speedy resolution.

I did all of what you suggested guided by the top level of Apple support. When it did not work, that was when he decided to record the problem second by second and sent to Apple engineering. My current work around is moving my albums out of folders. Once I did that, all the albums would sync.

my frustration is that this is a SIMPLE problem that should have been fixed easily. I guess Tharee are so many bugs with Catalina including dropping calls for iPhone 11 that this becomes a small potato. My discontent is in the lack of focus on “excellence” as this bug should not have existed to begin with. Guess I should get used to the mediocrity with Apple nowadays or move off to Android like half of my family have already done.

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

I made a Smart Album as shown below matching the name of the Smart Album to the name of the existing sub folder album. See the two screen shots below. So I was able to replicate a sub folder in my Travel Folder (Buenos Aires . . . ) in a top level Smart Album of the same name (or anything else you want to name it)

I was on with Apple Support regarding another issue and asked about why I was not able to sync my albums that were in folders on my Mac to my new iPhone 11 and I was told that Apple is no longer going to allow folders in Photos and that I had to move the albums I wanted to sync out of a folder

I’ve been trying to get this fixed for a few days now, thanks to everyone for the tips so far.

I think the problem lies with syncing the Folder “iPhoto Events” that’s where I had all my picture folders located. These now refuse to sync.

In Photo’s this was in the folder tree under “My Albums “,

to get round the sync issue I created a new folder / folders under the My Albums, so I right clicked on my album, create new album and copy my pictures across to the newly created folder and they now sync no problem.

under the Photo tab in finder I changed the selection to “selected albums” then selected all the albums individually missing out iPhoto Events.

I hope this all makes some sense and works when you try it.

Stu

So with iOS 13.3 and Catalina 10.15.2 released, I decide to install Catalina on an external SSD drive to test if bugs were fixed. As per above, same problem exists where albums under folders don’t sync at all to idevices.

However, taking all your advices, I decided to first duplicate those albums under folders that I want synced with my idevices (underlying photos don’t get duplicated, only internal references to their originals get recreated thus this doesn’t take up any meaningful space), then move these duplicates to the root under Albums.

Voila, they synced flawlessly, though the sync process takes a long long time (the progress indicator is practically useless).

At least I got what I wanted and Catalina 10.15.2 also addressed the music playlist icon issue.

Pls try this and see if this is stable with out any other issues. If so, I will then truly update my internal SSD to Catalina.

Just as an update.

I wrote directly to Tim Cook yesterday, explaining the disappointment in the new operating system and the problem of syncing photos with their own devices. Much to my surprise, I received a phone call & email from the Corporate Executive Relations of Apple. Although we played a bit of telephone tag we connected this afternoon. He advised that he is not tech support but he was going to set me up with a senior support representative, at my convenience, which was going to be tomorrow morning. He also said that he listened to my last conversation with Apple Support when I was told the tech rep would call me back and didn't. He advised that never should have happened and is going to look into that further.

About 30 minutes ago, I received a follow up call from him advising that he did speak to a senior support tech and that she advised that they are very much aware of this problem and are working on correcting it. She looked over what I had written and advised that I am already doing everything that can be done and that the "work around" that she was going to recommend, is exactly what some of us are already doing; moving the albums out of their folders so that the album is sitting directly under My Albums.

Lets hope that the next update includes the correction we are waiting for.

I removed 6 Smart Albums from inside a folder in Photos on my Mac Mini. Previously they did not sync to neither my iPad Pro nor my iPhone XR. After moving the albums to the root location, both sync routines worked as expected when these albums were selected in Mac Sync Settings.

All my devices are using the most current version of their OS.

Neal