I know this is an old post, but I think I might know why your program in saying 'yes' all the time.
The reason it might be always reporting that the server is up might be that if it is a linux box, iptables might have icmp host unreachable turned off. If that's the case then when your send call is done, it returns without error and in the gap between the nth and the (n+1)th send call, the OS reports an ICMP host unreachable, but due to the iptables rule, it gets dropped at the point of entry, never making it to the program. So your subsequent sends do not see any errors reported by the previous ones and it looks as if all is well.
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