Recipient who used to have iPhone. Messages always try to send as imessage instead of text.

I have a coworker who used to have an iPhone. Every time I message him, it trys to send as imessage and fails. Then I have to tap the ! and choose send as text.
I've delted the entire text string. I've completely removed him from my address book and re-added him. How do I tell the iPhone to always send messages to him as a text?
Thanks

Seems like your doing a lot of leg work for your friend.
Use the search function at the top right of the forum - this topic has been brouight up in many threads.
He/She would deregister their iphone from the apple server.. Sorry don't know the link or website.

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9:16 pm Sunday; April 12, 2015
 iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
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DKMac wrote:
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Hi,
The Name at the "To" spot should become a drop down and this should show you the various ways you can connect to them.
A "Chat" with someone can then switch between the various options if they have several ways.
As @mac.com and other Apple issued ID can also be AIM valid Screen Names you sometimes have to take a little care.
If you have made it to be an AIM chat though it should not switch back to iMessages even if that was the last method they used to contact you.
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9:52 pm Saturday; April 4, 2015
 iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

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This thread provided someone with a near identical problem a solution. Hopefully this helps you
https://discussions.apple.com/thread/5844705?tstart=0

Recipient who used to have iPhone. Messages always try to send as imessage instead of text.

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