I use asterisk behind my Linux firewall with no problem.  For IAX I have 
the firewall forward udp port 5036 to the asterisk box. Really simple nat 
setup.  My asterisk box also connects to other asterisk/IAX servers 
through nat from behind the firewall.  I'm not sure about sip at all but I 
know that IAX works fine.  I don't know anything about Winproxy but I 
would assume you could easily masquerade outgoing packets/connections and 
then for incoming connections forward port udp 5036 to your asterisk box.
AJ

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