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Unable to upload 16,000+ images and 400 videos to iCloud — all are in the Masters Legacy folder

I have transferred a 60,000 images, 2,500 videos, 300GB, iPhoto Library to Photos, and then started to upload the library to iCloud.

About 16,000+ images and 400 videos remain in the "Unable to upload" folder (I have tried a few times, logging in and out from iCloud and restarting the upload, but the result is the same).


The official advice from Apple support is to create a smart album with the condition "unable to upload", export the originals of this images and videos, cancel all the images in the smart album, and re-import them to Photos ("You might be able to fix this with steps below, but edits and keywords that you applied to these photos will be lost." https://support.apple.com/en-us/HT205409).


There are four problems with this solution:

  1. 1,000+ images have a wrong date either in the file data or in the EXIF data, and would have to be found and corrected with a new date manually.
  2. Fot the videos: For some reason, when re-importing the videos, Photos gives them the date of the import, not using the creation date of the file. So after importing, 400 videos would manually need to have their date corrected, first checking the date of the corresponding video which is already in the library.
  3. For some reason, when I try to create the smart album in Photos with the "unable to upload" condition, no images are found.
  4. 16,000+ images and 400 videos are a lot.


I discovered that all the images and videos that Photos is unable to upload to iCloud are found in a folder in the Photos library called "Masters Legacy". Making a smart search in Finder for all images and videos in that folder (which have lots of sub folders) I have been able to extract all these images and videos.


So in theory I could now re-import them to Photos, but I would still have the issue with 1,000+ images and 400 videos that would need to have their date corrected. And not being able to create a smart album it will be difficult to cancel the existing "unable to upload" images and videos from Photos.


A bit of a mess in other words.


Is there a way to help Photos uploading these images and videos to iCloud directly and avoid this huge hustle?


I am using a MacBook Air with Mac OS Catalina 10.15.7 and Photos 5.0.

MacBook Air

Posted on Oct 9, 2020 12:32 AM

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Posted on Oct 10, 2020 12:27 AM

Ah - that is a bit of a mess.


If you haven't already tried it it might be worth trying a library repair. Backup the library first though.

https://support.apple.com/en-us/HT204967

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8 replies

Oct 9, 2020 1:48 AM in response to Mats Lewan

I know in catalina, support for some formats has been removed, and the fact they are in masters.legacy makes me wonder if this covers your problem files (though I've not managed to find any specific info on that folder)


What format are the files you are having problems with?


EDIT - and please don't take offence, but sometimes we miss the obvious issue - you do have more than 300GB of Icloud space, don't you? :D

Oct 9, 2020 7:37 AM in response to Mats Lewan

OK, not that then.


Lets get back to this date correction thing and see if we can find a workround.


Normally the file creation date is stored in the EXIF data (though not always for videos). How is the date you want to keep currently stored in photos that you will lose if you export originals and re-import?


EDIT - done a bit of research. The masters.legacy folder seems to be a folder that holds original files from previous versions of photos that (for whatever reason) have not been renamed into the new long-alpha-numeric-filename format. This will be why they can't be uploaded because from what I read, I-cloud now needs the new filename format. So I think the only solution will be to re-import and we need to find a way to do that with minimum effort.

Oct 9, 2020 12:25 PM in response to TonyCollinet

Ok, thanks, the explanation for items in the Masters Legacy folder not uploading to iCloud seems reasonable, although it is unclear to me why images end up there at all, and so many images too! Appears like a major failure of the conversion software from iPhoto to Photos.


The dates I want to keep are the dates where I have manually placed the images using the "adjust Date and Time" command in the Photos application (or in the iPhoto application—this adjustment has apparently been kept through the conversion) , but I don't know how this date is reflected in the image data in the library.

Oct 9, 2020 2:33 PM in response to Mats Lewan

OK - I'm going to hope that is put into the exif data - but we'll see.


Can you select one of the images where you have had to do that, Export it as original, then open it with the preview app.


Then go Tools>show inspector. Does the date time original date match what you have put into Iphoto manually?


If yes, then the date should survive the export import process. Delete the exported image from photos, re-import it from the one you've just exported, and check if it still has the right date in photos.


Also when you export the original, tick the export iptc as xmp box. That should export a matched xmp file that holds any data youve put in in photos. (Hopefully). When you import with that file in the same folder as the image file, it should bring that data back.


If that all works you can be fairly sure it will work with the other 16K pictures.

Oct 9, 2020 4:23 PM in response to TonyCollinet

So this is what is happening.


First, when I click the thumbnail of the first image in the folder "unable to upload", it says in the info window that this is actually two images. And clicking on the thumbnail there are really two images that I can switch between. Very strange. The other image is not far away in the library, but have nothing in common, neither date nor file name. Then somehow, this effect disappears and the thumbnail points only at its own image.


Then, when trying to export this image as original, ticking the XMP box, the only thing that is exported is an .xmp file, no image file. If I don't tick the box, nothing is exported at all. It says "Export completed, 0 (of 0 files) were exported" (translated from Swedish). Same for any image in the "unable to upload".


If I try the option "Export 1 image" (shift-cmd-E) and choose to export it as JPEG (the original is JPG too), it fails. = (of 1 files) have been exported. Filename: F1050005.jpeg, Error: Unknown error (-1).


So, what I have are the image files that I managed to extract from the Masters Legacy folder, many of which have wrong creation date, as I explained in my first post.


Also, as I explained, for some reason when I create a smart folder in Photos with the condition "images that cannot be uploaded", it says that it doesn't contain any images. So I have no efficient way of cancelling the images that cannot be uploaded, even if I would be able to re-import these images and change the date manually.


I guess canceling them from the Masters Legacy folder in the library is not a good idea...

Unable to upload 16,000+ images and 400 videos to iCloud — all are in the Masters Legacy folder

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