Images not sending under iMessage

I recently encountered the problem of not being able to send any photos through iMessage to only one of my contacts. I had never had the issue before and is not occuring with any other contacts that I utilize iMessage with. I have re-booted phone and deleted and re added all of that contacts information. Any suggestions on a  fix as to why they fail to deliver?

After visiting Apple store and hours after rebooting phone to factory settings it still didn't work. So don't waste your time doing either of those. The simple fix was making sure both my phone and the "receivers" phones had been restarted. After he restarted his, worked like a charm. It happened again just a few days ago and we both restarted phone and worked correctly again. Good luck.

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    iOS: Troubleshooting cellular data
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  • Photos not sending through iMessage when on WiFi?

    Searched for an answer for this but so far no luck - sorry if this has already been solved elsewhere.
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    No, my AppleID is only linked to my iPhone and my MacBook Pro (which does not have messages installed).
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    Come on apple. You've basically secured the fact that this will be my last apple purchase. Funny that my friends with androids and windows phones never have any problems, isn't it?

  • My text messages to iphones are not sending as imessages.  Instead I have to copy and then send as text messages.

    Over the last couple of weeks, when I try to send someone an imessage, it won't sent and instead I have to click on the message and choose the option, 'send as text message'.  I haven't changed any of the settings other than install ios7.  Please help.

    Hi,
    This issue is usually caused by some anti-virus programs, disable the anti-virus program you have on the PC, check if this issue will happen again.
    You may also run Outlook in Safe Mode to determine if it's 3rd-party add-ins related:
    Press Win + R and type “outlook.exe /safe” in the blank box, then press Enter.
    If there’s no problem viewing html emails in Safe Mode, disable the suspicious add-ins to verify which add-ins caused this issue. Some security programs may have such add-ins intergrated with Outlook.
    Regards,
    Melon Chen
    TechNet Community Support

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