qmail and SSL: handshake failure:s23_lib.c:188

lucmove · 09-22-2009, 09:57 PM

Can someone help me fix this? I want to enable SSL on my qmail server, by far the most secure and difficult to configure MTA in the world. I followed these instructions and pop3 is working, only SMTP is being difficult: I can't send any test message with Kmail. Granted, Kmail doesn't help much either, but I test the connection with my server and get an error:

Code:

[213-0]~> openssl s_client -crlf -starttls smtp -connect mydomain.com:465                                                  ~
CONNECTED(00000003)
didn't found starttls in server response, try anyway...
16174:error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure:s23_lib.c:188:

[214-0]~> openssl s_client -crlf -starttls smtp -connect mydomain.com:25                                                   ~
CONNECTED(00000003)
didn't found starttls in server response, try anyway...
16191:error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure:s23_lib.c:188:

I have googled that and similar error messages, but can't reach any useful conclusion. I have also tried many sample configurations posted in old discussions. This is tough stuff.

Granon · 10-09-2009, 05:55 AM

Sorry I can't help you with configuring qmail.

However your use of s_client for testing is slightly off.

IIRC port 465 is intended to be SMTP over an SSL connection, not tcp with starttls. So instead you'd need to run:

Code:

openssl s_client -crlf -connect mydomain.com:465

Also you could add the "-debug" flag to have an idea about what's happening, both attempts were seemingly complaining that the service hadn't advertised starttls.