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I've setup ispconfig3 on my debian six server, and here is a little smtp over ssl:

The server is postfix

AUTH PLAIN (LOL!)
235 2.7.0 Authentication successful

MAIL FROM: lol@lol.com
250 2.1.0 Ok
RCPT TO: lol@lol.com
RENEGOTIATING
depth=0 /C=AU/ST=NSW/L=Sydney/O=Self-Signed Key! Procees with caution!/OU=Web Hosting/emailAddress=postmaster@lol.com
verify error:num=18:self signed certificate
verify return:1
depth=0 /C=AU/ST=NSW/L=Sydney/O=Self-Signed Key! Procees with caution!/OU=Web Hosting/emailAddress=postmaster@lol.com
verify return:1
DATA
554 5.5.1 Error: no valid recipients

but, the thing is, if I just do a vanilla telnet over port 25 I can authenticate and send mail like a madman... hopefully this is enough information! (as opposed to 'mail.app can't handle ssl!')

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Not by a long shot. Provide the output from postconf -n and the relevant part of your mail log (the part containing the entire transaction from beginning to end). –  adaptr Dec 1 '11 at 12:58
    
Have you tried another RCPT TO: lol@lol.com? –  Andy Smith Dec 1 '11 at 12:58
    
possible duplicate of Exim TLS and Secure SMTP –  jj33 Dec 1 '11 at 14:53
    
Ooh, I like the automatic comments when you flag as a dupe, nice touch. It's not super obvious that the questions are duplicates since they're using different MTAs and @lol didn't say that he was using s_client to test, but he is, and they are =) –  jj33 Dec 1 '11 at 14:55
    
really, you're beautiful people. you can have a doctorate in methods in computing but if you simply are not well versed in using programs you still need community help! I <3 stack overflow. In terms of the actual duplicate post - what should I do? (since the tags and the title in no way reflect what is actually going on in the tty) ...? –  lol Dec 1 '11 at 15:04
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1 Answer

up vote 4 down vote accepted

Pressing "R" in an s_client session causes openssl to renegotiate. Try entering "rcpt to:" instead of "RCPT TO".

You might also try tools that are more suited to SMTP-specific testing, such as Tony Finch's smtpc or swaks.

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+1 for case sensitivity... you're never too old to forget what is and isn't case sensitive! –  lol Dec 1 '11 at 15:08
1  
To be clear, s_client is just wrong here. You were correct in principle for using "RCPT TO". It's completely braindead that a plain text "R", in a tool that's made for typing text into, causes a renegotiate. The fact that you can get around it by using "rcpt to" is just a way to work around the bug/poor implementation decision in s_client. –  jj33 Dec 1 '11 at 15:11
    
Thanks, I will keep that in mind - I'm migrating from a play server -> a production one (with real ssl!) and so I haven't used all the security tools before, just learned about the unsecured transport protocols :) –  lol Dec 2 '11 at 5:27
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