SMTP AUTH

[Richard Stevenson]

On Tue, 25 May 2004, Noah wrote:

> sendmail-8.12.11
> freeBSD-4.9-STABLE
>
> I must be doing something wrong.  SMTP AUTH is not working very well for me.
> I have been trying to authenticate with user and password to port 25.
>
> I prefer to send all auth user and password information with SSL encryption.
> would like SSL Version 3 encryption.

You've got "This server requires a secure connection (SSL)" enabled for 
the SMTP server in Outlook?

> I am using microsoft outlook on windows XP machine to do the sending.  I have
> the username and password defined.
>
> I have configured outgoing mail requiring authentication then clicking both
> with Secure Password Authenticaiton and without.

That should be "without" for SPA.

> this is the error ending up in /var/log/maillog
>
> --- from the Maillogs ---
>
> May 21 16:19:33 typhoon sm-mta[64503]: i4LNJXxA064503:
> hostname.domain.com [10.10.10.10] did not
> issue MAIL/EXPN/VRFY/ETRN during connection to MTA
>
> --- snip ---

If you're requiring SSL, then my guess is that Outlook isn't seeing 
"STARTTLS" in response to EHLO.  You can confirm by getting a session log:

http://support.microsoft.com/?kbid=300479

And if you're running one of those !@#$@!$@!% antivirus products that 
scans outbound e-mail, *disable it*.  Those things all prevent SMTP AUTH 
and/or STARTTLS from working.

Cheers

Richard


-- 
Richard Stevenson

   If you can hear your neighbours firing small arms, they are using
   subsonic ammunition.
    -- Andrew Dalgliesh, in the Monastery