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Helpful answers
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Jan 10, 2013 4:36 AM in response to um who am i?by Dave Hutch,Connect the iPhone to your Mac and open the camera using Image Capture (in the Applications folder).
You can then select all photos in your camera roll and hit Delete.
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Jan 10, 2013 4:39 AM in response to um who am i?by Ingo2711,Did you try to disable photostream, let icloud remove the photos and turn photostream on again?
iCloud: How to delete photos from Photo Stream
I would remove all photos from the camera roll instead of tapping 500 times. Import one photo into iPhoto, after the import you should have the option to delete the pictures in the camera roll. After that sync your selection back to the phone.