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My Photos app on my Mac hasn't been syncing properly with iCloud since the Monterey Update

Ever since the Monterey update (about a month ago), my Photos app on my Mac hasn't been syncing properly with iCloud and my iPhone (and it always did before). Over the last month, I have tried a plethora of troubleshooting steps, but to no avail. I have roughly a quarter of a million photos and videos in my library so, as you imagine, every fix takes multiples days to finish. At this point, I really want it to just work, and not sure what exactly changed when I downloaded Monterey.

Posted on Mar 18, 2022 10:32 AM

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9 replies

Mar 19, 2022 9:41 AM in response to jeffreymcohen

OK - we may be on to something.


Sometimes those unable to upload items can block the sync process. You need to export them from photos to a folder, convert them to a compatible format, then delete from photos and re-import the compatible versions.


Also check the smart album I suggested.


Also worth answering the questions from Leonie below. And see her user tip about weeding out legacy media

How to Weed out Legacy Media in Photos fo… - Apple Community


Mar 20, 2022 7:45 AM in response to jeffreymcohen

The free storage is looking good, then.

The system version would have been helpful, if you upgraded from a system that still has been supporting 32-but applications. In that case you might have been running a system version that supported legacy formats for media files(About legacy media in iMovie for macOS - Apple Support).


For the "unable to upload" items you may want to look at this support document "Check the status of your library in Photos for macOS - Apple Support" to follow Tony's suggestion of exporting and reimporting. The problematic items need to be removed completely from the library, including "Recently Deleted", before you reimport them.


In my library the most recalcitrant items blocking the upload have been PDF images, very old videos, Live Photos created with third party apps, externally edited photos with unsupported color sync profiles.




Mar 18, 2022 4:19 PM in response to TonyCollinet

Hi Tony. Thanks for the quick reply! Yeah, I've let it go a month and it was "uploading" one by one through my library, but now it says the below (but Photos app on Mac still doesn't match what is in iCloud or on my iPhone). I think also I need to disable the sleep mode as you suggest.


Per you other question, my library is on a supported location (all stored on iCloud).


Mar 18, 2022 5:51 PM in response to jeffreymcohen

Where is your local library package? As well as being in iCloud it is synced to your mac. By default in the pictures folder, but with a library this size you may have it on an external drive. You can see where it is in preferences:


Do you have an "unable to upload" folder in the app. Or if you create a smart album with the condition "photos - is unable to upload" does it show anything?

Mar 18, 2022 11:31 AM in response to jeffreymcohen

I'm guessing that your upgrade to Monterey has triggered a complete new sync with iCloud - if your library is large this can take many days (or even weeks) even with the Mac on 24/7, so it may just be a case of letting it get on with it, leaving your mac on 24/7 with sleep disabled.


However, if your library is in an unsupported location (eg an external drive NOT formatted APFS or MacOS extended - or on a network drive, or on a synced drive like dropbox) then that may prevent the sync working correctly.


What does the sync status say at the bottom of the all photos view?


Mar 21, 2022 9:09 AM in response to TonyCollinet

Thanks Tony. In my previous reply, I meant to also say that my library is also stored locally on my Mac (I bought extra memory some time ago to accommodate the sheer number of photos) - see screenshot below. Per your 2nd question, there is an "Unable to Upload" folder in my library, but there's only 25 photos in it.




[Image Edited by Moderator to Remove Personal Information]

My Photos app on my Mac hasn't been syncing properly with iCloud since the Monterey Update

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