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My brother has a Windows Phone, and an iPad. Whenever I try to text him, it sends him an iMessage to his iPad, not a text message. Since he does not always have his iPad with him, he doesn't get my texts most of the time.

Is there a way to choose when a message is sent via iMessage, or via SMS?

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If you press and hold on the iMessage it will let you choose Send as Text Message. If you do this enough it will automatically start to send as a text message.

Also tell your brother to visit https://selfsolve.apple.com/deregister-imessage to deregister his iMessage so this doesnt happen with anyone else.

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