IMessage doesn't deliver photos to certain contacts

My friend and I both have iPhone 5's running iOS7. We can send and receive imessages just fine (blue quote bubbles) but when I send a photo it fails to deliver. This even happens in group chats where the I and the other people can see the photos but he can't. We've tried restarting but to no avail. Any suggestions? Anyone else having this issue?

Hi andrewmatoxy,
Try using the troubleshooting steps in the following article to help you address this issue with iMessage and MMS:
iOS: Troubleshooting Messages
http://support.apple.com/kb/ts2755
Thanks for using the Apple Support Communities. Have a good one!
-Braden

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Hey jordannicole6,
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http://support.apple.com/kb/TS2755
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Thanks for using Apple Support Communities.
For more information on this, take a look at:
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hnrm wrote:
Randomly my iphone well seem to decided to only send text messages to a certain contact when I am out of cell service. When i go to messages it says 'text message' and the send button it green only for that contact and there doesn't seem to be a way to tell it to send a immessage and it isn't that the contact is not a iphone cause most of the time it has no issue sending imessage.
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Hello sakputnam,
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gerio wrote:
Wooo.....
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Geri O

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IMessage doesn't deliver photos to certain contacts

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