Pictures in iMessage...

I cannot send pictures using iMessage or MMS to just 1 contact.
Can anybody provide a clue as to why or a solution??
Have tried all sorts to resolve but no joy!

No, the contact is my wife who is using her iPad over wifi. This problem only started about 4 weeks ago. I can send messages with iMessage but not pictures. Never had a problem before that. It just seems strange that she is the only contact I cannot send pictures to.

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having iPhone 5 with iOS 7 (the newest one) and having problem with sending pictures via iMessage. The picture is usually sent and marked as "delivered" but after few seconds it´s showed again as "undelivered" with red exclamation mark. I have tried to reinstall the iOS, I changed the phone at all (like to different piece of device) and the problem is still there.
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BR
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Hello there, Martinacep.
It seems you were referred to us from the very article that provides some troubleshooting recommendations for issues with sending attachments via MMS:
iOS: Troubleshooting Messages
http://support.apple.com/kb/TS2755
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If you can't send and receive MMS
You will need these to send and receive MMS:
An iPhone 3G or later
iOS 3.1 or later
A cellular data connection (MMS isn't available if you're using only Wi-Fi)
A domestic MMS plan from your cellular provider. You might need an international messaging plan to send MMS to an international contact (Contact your carrier for more information.)
A roaming MMS when using a cellular provider's network that is different from your billing cellular provider's network (Learn more about roaming and contact your carrier for more information.)
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Go to Settings and turn airplane mode off.
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Make sure that you have a cellular data connection in the status bar of your iPhone.
Go to Settings and turn Wi-Fi off. Open Safari and navigate to www.apple.com to verify that you have a data connection. Turn Wi-Fi back on to continue using Wi-Fi for other features. If your cellular data connection isn't available, follow these steps.
Make sure that you can send and receive SMS. If you can't send and receive SMS, see the "Issues with sending and receiving SMS" section, above. MMS might not be available while you're on a call. Only 3G and faster GSM networks support simultaneous data and voice calls. Learn more about which network your phone supports.
Restart your iPhone.
Tap Settings > General > Reset > Reset Network Settings on your iPhone.
Remove your SIM card and insert it again.
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Thanks for reaching out to Apple Support Communities.
Cheers,
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All of a sudden this afternoon I can no longer send pictures using iMessage to a specific contact. The contact is the other phone in my house which is an iPhone 4 and I am using a 4s. The iPhone 4 can send photos to me using iMessage with no problem but I cannot send any to that one. iMessage will show delivered and then change to not delivered, I have turned iMessage off and on, done soft and hard reboots, and done a restore as well from a time when it was working. In every scenario I get the not delivered message. Can anyone help with this?

of course all 3 iphone 4s are using there own apple id's
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the exact settings as the 4s that shows a phone number
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After update 6.1.1 I can't send pictures on iMessage and im on wifi. But if I send the picture as a text message it going through. I sent out several pictures before the update now I can't.

HI,
So you have updated past this point ?
http://support.apple.com/kb/TS5419
There also seems to be no issues listed here.
http://www.apple.com/support/systemstatus/
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I am having issues sending pictures via iMessage to only one of my contacts. They can send me pictures through iMessage so why are mine coming back undelivered?

Have managed to get it working.
It might be as simple as switching the other phone completely off, and resetting it...
I say this because I have no idea how I finally managed to get it working again. I tried so many things. Removing all the iMessage addresses. Sending messages from the computer, iPad...etc and found that the weakest link was my wife's phone. It wasn't receiving iMessage pictures from ANYONE (not just me). That allowed me to narrow down the possibilities somewhat.
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Pictures in iMessage...

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