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using openssl s_server to investigate exchange server encryption negotiation

Hi Folks,

Seriously?  I can't ask a question about anything except Exchange Server 2013?  Sheesh...  It is probably the same answer for both 2013 and 2003, but really, ...

I have an old, old, old version of Exchange Server (Exchange 2003) and I am trying to establish a connection with an upstream SMTP Smart Host, which uses various forms of authentication and encryption.  I can use "oppenssl s_client -tls1 -starttls smtp -crlf -connect <host:port>" to investigate what the upstream SMTP Smart Host wants, but I need  to use "openssl s_server ..." to investigate what Exchange Server 2003 is offering in the encryption/authentication negotiation, and I don't have the experience to know how to set the command.

Does anybody know how to set a command with openssl that will mimic the upstream SMTP Smart Host and reveal the encryption/authentication negotiation of Exchange Server 2003 as seen by the upstream SMTP Smart host?

Thanks for the help,

Chris.


Thanks for the help,

Chris.


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