Testing Exchange 2007 IMAPS using OpenSSL

I was trying to find out why Thunderbird wasn’t working with Exchange 2007 IMAPS (SSL). So I started testing this using OpenSSL using the following command.

openssl s_client -connect imap.host.ca:993

However, I was able to use the LOGIN command, no command would return an error or any information. I did some searching and found that you need to include “-crlf”, from the man page.

-crlf
this option translated a line feed from the terminal into CR+LF as required by some servers.

Adding this option then allowed me to login successfully. That was a good waste of 2 hours.