Postfix + AUTH/TLS + Outlook/OE problem

[Darren Pilgrim]

Adrian Gonzalez wrote:
 > Hello
 >
 > I'm seeing some very strange behavior with Outlook 2003 and Outlook
 > Express trying to send mail using TLS/SMTP Auth with Postfix 2.3 and
 > FreeBSD 6.1-STABLE
 >
 > It seems like Outlook/OE don't like the SSL handshake for some
 > reason.  They connect to the server, issue STARTTLS, and disconnect
 > during the handshake, giving an "Error Number: 0x800CCC0B".  I've
 > tried both STARTTLS and using 'wrapper mode' on port 465 with the
 > same results.

Which version of Outlook Express were you using?  Outlook Express 6 
doesn't support STARTTLS, only wrapper-mode.  OE6 also also has a broken 
SASL implementation (set broken_sasl_auth_clients=yes).  Yay for Microsoft!

Have you modified your cipher settings in postfix?  FYR, Outlook XP/2003 
and Outlook Express 6 prefer 128-bit RC4-MD5 and do not support AES, 
whereas Thunderbird supports and prefers AES256-SHA.

On my own mail server, I can send email using all four clients through 
STARTTLS+SASL (Outlook and Thunderbird) or SMTPS+SASL (OE).  The server 
is FreeBSD RELENG_6_1 with the stock OpenSSL and postfix 2.3.1 with 
default tls_*_cipherlist settings.

Be happy to compare configs off-list, postconf -n and the like.

P.S. You may want to retry this question on postfix-users.  You'll have 
better luck if you're willing to wade through the usual "ditch MS" rude 
commentary.

P.P.S. Please configure your mail client to wrap lines.

-- 
Darren Pilgrim