Connecting to Exchange Server 2003 over POP using openssl s_client

Posted by Andreas Jansson on Server Fault See other posts from Server Fault or by Andreas Jansson
Published on 2010-05-12T12:48:36Z Indexed on 2010/05/12 12:56 UTC
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I'm trying to fetch emails programmatically from Exchange 2003 over POP. As a proof of concept I'm trying to connect using openssl s_client.

I've started the POP service on my Exchange server. Trying to connect using

openssl s_client -connect MYEXCHANGESERVER:995


20303:error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure:s23_lib.c:188:


openssl s_client -connect MYEXCHANGESERVER:995 -starttls pop3



Forgive a newb - I'm basically shooting wildly in the dark with no idea on what I'm supposed to be doing. In the past I've read my GMail over openssl s_client, and setting up those certificates was easy and well documented. I would imagine I need to set up some sort of certificate here as well, and I've looked a bit at using a .pfx file. But like I said, I'm completely lost here.

Thankful for any advice,


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