HT204065: If you can't send or receive messages on your iPhone, iPad, or iPod touch
Learn about If you can't send or receive messages on your iPhone, iPad, or iPod touch
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Helpful answers
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Apr 23, 2016 9:46 AM in response to Lahjonesby ZikzakCorp,Have you checked to see if the other user on the phone not receiving the messages has the number blocked? If it's an iPhone, go to Settings > Messages > Blocked.
Block calls and block or filter messages on your iPhone, iPad, or iPod touch - Apple Support
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Apr 23, 2016 5:20 PM in response to ZikzakCorpby Lahjones,It happens with multiple people. The send button turns green before it is sent.