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Helpful answers
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Dec 9, 2015 11:55 PM in response to sashtonby Ingo2711,Are you using the steps mention in this article to transfer the photos?
Sync photos from your computer to your iOS device using iTunes - Apple Support
Are you taking photos in HDR mode? If yes, try to disable HDR and test if you can sync the photos back to your iPad.
Troubleshooting for Photo Stream is covered in this article: