socket.py for IronPython now has an SSL support.
http://sparcs.kaist.ac.kr/~tinuviel/fepy/lib/

ssl.py can use either SslStream from System.Net.Security or
SslClientStream from Mono.Security.Protocol.Tls. This is because
System.Net.Security classes are new in .NET 2.0 and not implemented
(stubbed) in Mono, but Mono had its own implementation of SSL before
.NET 2.0 came.

Python side of interface is exactly same as socket.ssl of CPython. I
added a new example using poplib's POP3_SSL class to connect to GMail
POP3 SSL server, that you can run with both CPython and IronPython.
http://sparcs.kaist.ac.kr/~tinuviel/fepy/example/pop3s_test.py

Enjoy!

Seo Sanghyeon
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