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[iaik-ssl] newbie questions

i have some client/server stuff. i want to swap out the sockets for secure-sockets.
is it a trivial job or will i have to get into certificate issues at the server?
has anyone come across this error?
HTTP/1.1 502 Proxy Error ( SSL port specified is not allowed.  )
Via: 1.1 spirit-proxy
Pragma: no-cache
Cache-Control: no-cache
Content-Type: text/html
i am using the "CONNECT" method to our proxy, hoping to get secure stuff
through to a server on the internet.
also, has anyone got "ntsniff" working on Windows 2000 Pro? if not, is there another
free sniffer about that anyone would vouch for? (I couldn't get Network Monitor from
the w2k server edition, for some reason it would not install)