The OP touches on a problem very important to network communication theory.
It's usually introduced to computer science students in the form of a thought problem. I wish I had a reference to this (it's a classic, textbook problem), but my google-fu isn't cooperating today. Anyway, it goes something like this:
Two blue armies wish to defeat the evil red army. The two blue armies are on opposite sides of the red army. The blue armies can easily defeat the red army, but only if they attack together, simultaneously. If they fail to attack simultaneously, the red army would easily defeat one of the blue armies followed by the other.
The two blue armies can communicate with each other only by sending courier spies from one side to the other, by going
through the red army. However, there is a small but finite possibility that a courier spy can be captured by the evil red army as it passes through. (And there's no going around the red army -- in order to pass a message, the courier must pass through the red.)
So the question is, "is it possible for the blue armies to defeat the red army with 100% certainty?"
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And the answer, it turns out is "no." It can be done with a fair amount of certainty, but never 100%.
A good starting point might be for the right side to send a courier over to the left side with the message, "We attack Tuesday at dawn. Send a courier spy back this way with an acknowledgment that you received this message. We won't attack if we don't receive the acknowledgment."
Suppose that both couriers made it across successfully. The right side blue army is now ready to attack Tuesday at dawn. But the left side gets to thinking, "hmm. Ya know, I'm not sure if my acknowledgment courier spy made it across. If he was captured, the right side won't attack and we'll be defeated."
So instead of sending back a simple acknowledgment, the left side sends back this message, "We got your message to attack Tuesday at dawn. This is the acknowledgment message that you requested. Please send another courier spy back this way acknowledging that you received this acknowledgment. If we receive the acknowledgment of this message, we will also attack Tuesday at dawn."
And continuing that thought process, it's soon realized that in order to attack with 100% certainty, an infinite number of courier spy messages are needed.
[Edit: And what's more, since there is a finite probability that any given courier spy would be captured, and since it only takes a single capture to foil blue's plans, the probability of blue succeeding tends toward 0 with increasing number of acknowledgments. So a vast number of acknowledgment messages is definitely not the best approach.]
The real-world application to this is network protocols such as TCP-IP. Acknowledgement messages are built into the protocol. With single a acknowledgment it's reasonably certain that the desired information was transferred successfully. But it can never be known with 100% certainty.