Why won't my iMessages go through to my friend but works with others? iMessage is activated on both phones

I can iMessage friends and they receive my messages except for one friend who has not been receiving my iMessages sent to him. If I turn off iMessages he receives my text messages. I can receive iMessages from him and reply but I can not initiate the iMessage. My iMessages are going out successfully to others. I have done a hard restart, turned iMessage off and back on, and deleted his contact info and added it back to my contacts.

Is there a not sent indicator on the message initiated by you, or is the message sent but not received?
If no problem with anyone else and the only problem is on the recipient's end, doubtful the problem is on your end.
What has the recipient done?

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3. Press the Power button to select “RECOVERY.”
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5. Using the volume button, scroll down to “Wipe cache partition” and select it.
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Why won't my iMessage work with only one contact in my phone all my other iMessages send and they just got an iphone but all their iMessages are sending also. I've tried restarting my phone, deleting messages, contact, restarting network

Why won't my iMessage work with only one contact in my phone all my other iMessages send and they just got an iphone but all their iMessages are sending also. I've tried restarting my phone, deleting messages, contact, restarting network

Hello Jesslb23,
Thanks for using Apple Support Communities.
For more information on this, take a look at:
iOS: Troubleshooting Messages
http://support.apple.com/kb/ts2755
To resolve issues with sending and receiving iMessages, follow these steps first
Check iMessage system status for current service issues.
Go to Settings > Messages > Send & Receive and make sure that you have registered iMessage with your phone number or Apple ID and that you have selected iMessage for use. Learn more about troubleshooting iMessage registration if the phone number or Apple ID isn't available for use.
Open Safari and navigate to www.apple.com to verify data connectivity. Learn more about troubleshootingcellular data or a Wi-Fi connection if a data connection isn't available.
iMessage over cellular data might not be available while on a call. Only 3G and faster GSM networks support simultaneous data and voice calls. Learn more about which network your phone supports. Go to Settings > Wi-Fi and turn Wi-Fi on to use iMessage while on a call if your network doesn't support simultaneous data and voice calls.
Restart your device.
Tap Settings > General > Reset > Reset Network Settings on your iPhone.
If you are still unable to send or receive an iMessage, follow these steps
Make sure that the contact trying to message you isn't blocked in Settings > Messages > Blocked.
Verify that the contact you are attempting to send a message to is registered with iMessage.
If the issue occurs with a specific contact or contacts, back up or forward important messages and delete your current messaging threads with the contact. Create a new message to the contact and try again.
If the issue occurs with a specific contact or contacts, delete and re-create the contact in the Contacts application. Create a new message to the newly created contact and try again.
Back up and restore your device as new.
Best of luck,
Mario

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http://support.apple.com/kb/HT3529
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http://www.apple.com/ca/ios/messages/
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Troubleshooting iMessage Issues: Some Useful Tips You Should Try
http://www.igeeksblog.com/troubleshooting-imessage-issues/
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Why won't my iMessages go through to my friend but works with others? iMessage is activated on both phones

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