Mac iMessage won't sync to iPhone after Airplane Mode

Hello all,
Please help! I turn my phone to airplane mode in meetings so that it does not buzz and bother people. Sometimes I will correspond with a colleague via the Messages app on my Mac during the meeting.
BUT when I turn my phone on just 30 minutes later whole conversations I had on the mac will NOT sync to iPhone. I try everything but I can never get the iPhone to sync to the history on the Mac app.
Further, sometimes if I have both the Mac and the iPhone on airplane mode, I will only know I receive an iMessage when it pushes to my Mac after reconnecting, NOT my iPhone. So now I am paranoid about going on Airplane mode because if I can't get to my Mac soon enough, then I may miss a ton of iMessages.
Does anyone know how to fix this issue? Or have an idea as to what is going on?
I have checked the settings and my phone number, and two email addresses (my persona and my iCloud one) all are checked on both the Mac and the iPhone.
My Mac is: MacBook Pro, OS X 10.9.5
My iPhone is: iPhone 5, iOS 8.3
Thank you so much!!

... i should add that my mac calendar icon doesn't say "icalendar" like it used to.  does that make a difference?

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