IMessage sent as text message

I sent a friend an iMessage but it was sent as a text instread.  What I don't understand is I sent that same message thru the Messages app on my Mac and the friend recieved it on his iPhone as an iMessage.  So I seem to be able to communicate with him thru the Mac messages but when I use my phone it goes as a text.
Other friends with iPhones I can iMessage just fine.
I know iMessage requires wifi but I assume my wifi is ok if I can Imessage other people and my friend's must be ok as ge gets the iMessages I send from the computer.  I just can't figure out why when I use my phone it goes as a text.

What's odd though is I have several contacts where this happens.  One other thing I don't understand though is let's say the iPhone wants to send it as a text but i send it from the computer where it can only iMessage.  If my friend can't get iMessages at that time will my iMessage from the computer eventually get delivered?
It seems once my iPhone starts sending iMessages as texts to certain contacts it takes it a while to revert back.  If I were to turn off the send as SMS option and iMessage wern't available would it eventually go thru?

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