Dunno if this'll help or not, but if you use openssl on the server or client side like this:
in place of your client code:
openssl s_client -debug -connect servername:port
or
in place of your server code:
openssl s_server -debug -accept port
and make (or receive) a connection you should get a wealth of info that might help figure out the timing problem.
-beernuts
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