iCloud Photo Library and iTunes Sync Solutions

The new iCloud Photo Library feature in iOS 8.3 and OS X 10.10.3 is a HUGE improvement over Apple's old My Photo Stream. We’ve been using it ourselves for a few months now and it’s been working really well.

There is however, one particularly exasperating problem that people are encountering when they try to enable iCloud Photo Library in their Settings or during their upgrade to iOS 8.3. They see a very scary warning message like this:

Photos synced from iTunes will be removed.

Syncing photos via iTunes is not supported when iCloud Photo Library is turned on.

XX photos will be removed

Most sane people confronted with a warning like this will tap Cancel and forget about iCloud Photo Library forever. After all, who wants to have a bunch of their valuable photos deleted?

However, we’d like to suggest that the benefits of iCloud Photo Library are sufficient that you should consider going ahead anyway if you’re willing to follow the steps in the rest of this blog post.

What Does the Warning Mean?
First of all, the warning means business: if your iOS device contains photos that you’ve synced at some point in the past via the iTunes app running on your Mac or Windows PC, they will be deleted from your iOS device when you enable iCloud Photo Library. Bummer. (It’s hard to understand why the Apple iOS engineers didn’t take the time to do something better, like maybe ask if you'd like to keep the photos even if they no longer sync...)

That’s the bad news, but the good news is that, assuming you still have all those photos on your Mac or PC, it’s pretty straightforward to restore them to your iOS devices using iCloud Photo Library itself.

If you don’t still have the photos on your Mac or PC, then definitely do NOT enable iCloud Photo Library because they will indeed be deleted forever.

How To Restore Previously Synced Photos to your iOS Device

If you decide to go ahead and tap Remove Photos when you enable iCloud Photo Library, the next sections describe how to then restore the removed photos back to your iOS device from either a Mac running OS X or a PC running Windows.

Mac OS X
If the photos that you previously synced to your iOS device are still on your Mac, follow these steps.

  1. Upgrade the OS X operating system on your Mac to Version 10.10.3. If for some reason you cannot upgrade it to 10.10.3 (e.g., insufficient disk space) then you should follow the steps below for Windows.
  2. Once your Mac is running 10.10.3 your old iPhotos app will have been replaced with the new Photos app. So launch the new Photos app on your Mac and when prompted, enable iCloud Photo Library. This will (eventually) upload all your photos to iCloud where they can then be downloaded to your iOS devices. 
  3. Then, back on your iOS device(s) enable iCloud Photo Library (in Settings or during the upgrade to iOS 8.3) and go ahead and tap the scary Remove Photos when prompted.

    Depending on how many photos are on your Mac and iOS devices, within a few minutes or possibly hours, all of the photos on your Mac will be copied to your iOS devices and all of the photos on your iOS devices will copied to your Mac. From then on, all your photos will stay in sync between your Mac and your iOS devices without you ever needing to use iTunes to sync them again.

If the photos that you previously synced to your iOS device are still on your on your Windows PC, then you have to use the iCloud.com web site, since there isn’t an Apple Photos app for Windows (at least not yet).

  1. On your Windows PC (or Mac), use your web browser (e.g., Internet Explorer) and go to www.icloud.com. Login using the same iCloud username and password that you’re using on your iOS devices.
  2. On your iOS device enable iCloud Photo Library (in Settings -> iCloud -> Photos or during the upgrade to iOS 8.3) and tap the scary Remove Photos when prompted. As mentioned above, the synced photos will be removed, but the next step will put them back.

    Depending on how many photos are on your iOS devices, within a few minutes or possibly hours, all of the photos on your iOS will be copied to iCloud and you should be able to see them appear in your Photos page on iCloud.com.
  3. Now go to the Photos page on www.icloud.com in your browser and click the Upload button at the top of the page. This will then open a file chooser that will let you choose the photo files that you want to upload to iCloud. For example, you can navigate to your My Photos folder and select the photo (.jpg, .gif, etc.) files that you want to restore to your iOS devices. Once you have the files selected, click Choose and the chosen files will be uploaded to iCloud. 

    Depending on how many photos you’ve uploaded, they should all eventually appear on your iOS devices in the Photos app.

Since you can no longer use iTunes to sync, there will no longer be any automatic “sync” from Windows. Each time you add or make changes to photos on your Windows PC, you’ll have to again go to iTunes.com and manually Upload the photos so you can see them on your iPhone or iPad. (Maybe some day Apple will update iCloud for Windows to support iCloud Photo Library, but the current version only supports the old My Photo Stream.)

Photo Albums
One of the features of using iTunes to sync photos to your iOS device was that you could choose to only sync specific albums or folders.

For example, if you’re an architect and you only wanted to sync a small portfolio of photos from your Mac to your iPad, you may have created a “Portfolio” album in iPhoto and then used iTunes to selectively sync only that album to your iPad.

If you’re using the Photos app on the Mac, iCloud Photo Library will include all of your photos iCloud Photo Library - it doesn’t have album-level selectivity. However, all of the albums on your Mac will sync to your iOS device so you can selectively see just the photos in, for example, your Portfolio album. And if you choose the “Optimize iPad Storage” setting in Settings -> Photos, your possibly unwanted photos shouldn’t consume any space on your iPad (typically just the space for each photo's small “thumbnail”).

On the other hand, if you use iCloud.com instead of the Photos app or you’re a Windows user, you can manually upload only the photos you want, but it’s strictly a manual operation. And, worst of all, if you let iOS "remove" all your previously synced photos from your iOS device when you enable iCloud Photo Library, all the photos will also be removed from their folders (though the folders themselves seem to be retained). In other words, any work you did to put the synced photos into albums on your iOS device will be lost, even after you restore your photos from Windows via iCloud.com.