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Transfer photos from icloud drive to photos

I have approximately 30GB of photos I want to transfer from Dropbox to iCloud Photos, and the experience so far has been absolutely abysmal. I am seeking the best way to get these photos onto iCloud photos. I was prepping to move to Mac, but I’m not going to now how I see how buggy some of the software is,


I am using a Windows 10/11 PC, an iPad Pro 11” latest and iPhone XS Max.


  • I downloaded the photos from Dropbox and copied them over to iCloud photos on windows. The iCloud for Windows app is EXTREMELY buggy. If I copied the files to iCloud photos, only 1000-2000 would upload despite 6000 photos being in the folder. The iCloud app would get stuck at “waiting for xxx files to upload” and it stayed there for WEEKS (I have been at this for about 2 months now). I reformatted the computer, reinstalled iCloud etc and same problem. Even if I did it in smaller batches. The worse part is it added hundreds of duplicates every time I tried.
  • I copied the photos to iCloud Drive where miraculously they all uploaded fine! Yay! But even now they’re on Apples servers, I cannot simply copy them to photos!! I tried in the browser and in files on the iPad as well as looked for an import option in photos. Surely nobody would overlook this basic functionality so I must be missing something?
  • If I actually try to get the photos from iCloud advice and save them to my iPad so that they automatically update (though surely this double handling can’t be required), I can’t, because there’s just too many to save. I had issues doing it in batches too.
  • So I saved the photos to a USB stick so that I could simply copy them to my iPad. Except I can’t copy them to photos, only to files, where I have to save them from there. Fine, except the files app doesn’t work. Even in a small batch of 20 photos, if I select 20 photos and press “share” it will come up with “Save 6 Images” despite the fact I have 20 selected. Played around with this for a while and ended up with tonnes of duplicates.
  • I cannot even get all my photos onto Files from the USB stick (Sandisk Extreme SSD), as when I select all my photos, the app crashes.
  • I tried manually uploading the photos to iCloud using the Website, the progress bar got to about 50% then stalled. Some images did go in, not sure how many, most seemed to be duplicates.


I am open to any suggestions, if theres a way to force photos to upload? Or to simply copy images from Drive to Photos?


If not, I’m open to a job. The US is a bit of a commute but I’m an experienced developer, project manager and executive and easily bribeable.

Posted on Nov 7, 2021 7:07 AM

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Question marked as Top-ranking reply

Posted on Nov 8, 2021 1:11 AM

The problem is that the iCloud app on Windows doesn’t work for uploading photos. So these guides simply don’t work.


Syncing photos between all my devices is exactly what I want to do, but it can’t seem to do it.

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5 replies

Nov 8, 2021 11:22 PM in response to brbo

Yes, everything is set up correctly.

The issue is that the photos app simply gives up on upload and cannot complete it. It uploads SOME photos, but not others. And it duplicates them.


I’m going back to Dropbox because iCloud just seems super buggy and it’s meant to “just work” which means there is no support or alternatives for when it doesn’t work as intended. I’ve just realised my passwords are not syncing across devices either - with my iPad and iPhone having different passwords for one site, and my pc not having any password for that site.

Nov 7, 2021 10:20 PM in response to Dredgy

Seems iCloud is mainly for syncing the files you choose from one device to another, or all, of your devices.


Apple have articles online, many with steps to follow.

Sometimes older, known methods have been changed / updated.


Keep your photos and videos up to date with iCloud Photos

https://support.apple.com/en-au/guide/icloud/mm8b32f3ae27/icloud


Set up iCloud Drive on your Windows computer

https://support.apple.com/en-au/guide/icloud-windows/icw0144825a5/icloud


View, add or remove iCloud Drive files in iCloud for Windows

https://support.apple.com/en-au/guide/icloud-windows/icwddbc813bd/icloud


iCloud for Windows User Guide

NB: Click "Table of Contents" at the top, for all the topics, leading to detailed articles.:

https://support.apple.com/en-au/guide/icloud-windows/welcome/icloud


Hope this helps :-)

Transfer photos from icloud drive to photos

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