Re: Postfix + AUTH/TLS + Outlook/OE problem

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
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