Why is Messages saying all my Sent messages "could not be delivered" when they have gone through?

Within the last few days, Messages on my Macbook Pro (Retina, 15") is showing the "could not be delivered" red circle with a white "!" after every message I send out to another Messages user. I can see that the messages were delivered by looking at the same thread on my iPhone (iOS 7.1) and the recipient gets all of them as well. The recipient is seeing these messages appear on their iPhone -- and likely their iPad mini as well.
I've tried deleting the conversation and restarting the Macbook Pro thinking it could be a temporary glitch. The problem still occurs, though. Everything I send from Messages on my laptop (to the same user) shows as not having been delivered, though they have been.
Any thoughts? Solutions?
Thanks in advance!

Hi,
Once you have sent an iMessage the server "pushes" at the contact and all the devices they have linked to the iPhone Number or Apple ID.
It continues to Push for some time if one devices does not give a response.
However in the meantime the iMessage may have been delivered to an iPhone of iPad.
It may not get delivered to a Mac for instance and it is the feedback that this has not happened that can give you the "Not Delivered" message.
Of course that are variants depending if you are "aiming at" the iPhone Number rather than the Apple ID and if the iPhone is not on WiFi or a suitable Carrier alternative like 3G.
It's a bit like sending an email to 20 people and only getting 19 acknowledgements.
8:32 pm Tuesday; April 1, 2014
 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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