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In an attempt to troubleshoot an apparently "stuck" upload process with iCloud Photo Library, I tried a suggestion I read about in Apple's own forums: Disable and then Re-Enable iCloud Photo Library.

Unfortunately, after doing so, I've apparently run into an unforeseen edge case from Apple. My iPhone refuses to re-enable iCloud Photo Library due to insufficient iCloud storage. The assumption from iCloud seems to be that all my local photos would be "new" to iCloud. In reality, my iCloud storage is adequate, since all my local photos should be detected as duplicates and not actually added to the iCloud Photo Library.

At the moment, it appears my only option is to upgrade my storage just for the purpose of re-enabling this feature. Am I overlooking any other clever solutions?

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A suggestions I've seen on other Q&A forums is to use another device with iCloud Photo Library enabled and wipe the Library so there is enough space for all your photos to be re-added.

If you don't have another device with iCloud Photo Library, I believe you can delete the files from General > iCloud > Storage > Manage on an iDevice.

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    Deleting all the photos from iCloud would possibly solve the problem, unfortunately with the disadvantage of having to re-upload around 12GB of photos and videos. Another option might be to do the reverse: delete all local files and re-enable iCloud Photo Library. Downloading should be faster than uploading. My biggest concern in either scenario is that iCloud might "misinterpret" this act as a desire to delete those files completely. – Avian00 May 4 '15 at 15:03
  • @Avian00 Deleting local files doesn't seem to effect photos on iCloud (tested it) but iCloud isn't the most stable platform around so I'd recommend waiting longer for the upload but retaining a local copy. – Séb May 4 '15 at 15:06
  • I'm looking for a similar solution to this... except my library is 680Gb so deleting it and re-downloading isn't really an option! – Designer023 Jan 19 '16 at 20:44
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it's year 2019 and I encountered the same problem on iOS 12.4.

Here is how I solved it just now:

  1. Goto Apple ID > iCloud > Photos;
  2. Turn on iCloud Photos. There will be a popup prompting insufficient icloud space;
  3. Press the "upgrade plan" (or something similar, I can't remember the exact words) in the popup, then a new window shows with several icloud plans;
  4. Note that there is a button at the bottom saying "continue without purchasing". Press it;
  5. Then, the iCloud Photos option should be on, and the Optimize iPhone Storage is automatically chosen. You can turn it back to Download and Keep Originals if you like.

Apologize for not showing screenshots but I hope the above message could help others who run into the same issue in the future. ;)

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You could create a new library in Photos, enable iCloud Photo Library, and let Photos download all your photos and videos. Once you've verified all photos and videos downloaded properly (this could take a great deal of effort!) you could then delete the old library from your hard drive.

To create a new library in Photos:

  1. Hold down the option key while opening the Photos app. A window should appear which, among other things, has a Create New button.
  2. Click the Create New button which should open a Save As dialog.
  3. Enter the name you want to use for the new library and choose a location.
  4. Click OK and you should be using the new library at this point.
  5. Enable iCloud Photo Library as usual in the settings and let the downloading commence!
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You can't simply create a new Library in Photos, enable iCloud Photo Library and let Photos download all your photos and videos to the Mac because only one library on a Mac can be the "System Photos Library" and only the System Photos Library will sync with iCloud. The first Photos Library that is created is the System Photos Library, you can't designate a new Photos Library to be the System Photos Library. See link below. I suppose you could completely move the System Photos Library off of your drive (or Archive it in Finder the remove it) and then create a new System Photos Library to sync the iCloud photos down to, but I haven't tested that yet. This seems to still be a huge problem that needs to be addressed. Temporarily logging out of iCloud on a Mac should definitely not require an entire Photos library re-download, it should just resync.

https://help.apple.com/photos/mac/1.2/index.html?localePath=en.lproj#/pht211de786

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You could delete all the photos locally before reenabling the iCloud Photo Library. That is, only if you're absolutely sure that all your photos are in iCloud. Then, with an empty local library, reenable iCloud Photo Library on the device.

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