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Helpful answers
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Jan 18, 2016 6:17 AM in response to bmilot56by jeremy_v,Hi bmilot56,
Thanks for participating in the Apple Support Communities.
It sounds like you're sending SMS/iMessages but it's unclear if they're being delivered to one contact.
You should see a red exclamation point next to messages if they're not delivered, as seen in If you can't send or receive messages on your iPhone, iPad, or iPod touch.
This article also has steps that can help with troubleshooting the situation.
Sincerely.
