Why do I get a "not delivered" message when using iMessage???

When I text my husband, the iMessage fails every time.  We only get texts from each other if not using iMessage and just using texting. 
We are having so many problems with iCloud!
I'm guessing we didn't set up the account right from the beginning. 
Can anyone pleae help?!!?

I've noticed that this happens a lot to me with some people who are connected to corporate wifi.

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