Run:

# tcpdump -n -i [interface facing client] -s256 'host 66.24.215.191'

See if they are actually attemping an SMTP connection and if
the socket is handshaking.  It doesn't sound like it.

Also, run 'netstat -tan' on both the client and server at the time of the
send/receive mail operation.

Note: No SMTP traffic is shown in your log below.

~BAS

On Sat, 28 Mar 2009, Jonathan Nalewajek wrote:

> Hello everyone,
>
> I just set up an Ubuntu 8.10 server, which purpose is to act as a web
> server and e-mail server.
>
> I have courier installed (courier-imap + courier-imap-ssl), and I also
> want to use courier as my smtp server (courier-mta and courier-mta-ssl).
>
> I configured Courier (using the web admin gui) and installed squirrelmail
> for a webmail client. I configured squirrelmail, and it is running
> flawlessly. I can send mail, receive mail, etc. No problems whatsoever (I
> am sending this e-mail from it).
>
> However, most of the people that will be using this server use Microsoft
> Outlook or Thunderbird. I tested both Outlook and Thunderbird, and
> although both can receive mail, neither can send mail.
>
> So my first thought was to make sure telnet could connect. Telnet does
> connect on port 25 and 465, and I was even able to send an e-mail via
> telnet commands.
>
> I then ran:
> $lsof -i :25
> COMMAND PID USER FD TYPE DEVICE SIZE NODE NAME
> couriertc 1397 daemon 3u IPv6 497068 TCP *:smtp (LISTEN)
>
> $ lsof -i :465
> COMMAND PID USER FD TYPE DEVICE SIZE NODE NAME
> couriertc 1432 daemon 3u IPv6 497107 TCP *:ssmtp (LISTEN)
>
> When I try sending an e-mail via Thunderbird or Outlook, here is what is
> in /var/log/mail.log:
>
> Mar 28 13:01:27 lucy imapd: LOGIN, user=jonnale,
> ip=[::ffff:66.24.215.191], port=[57210], protocol=IMAP
>
> It then eventually times out or just disconnects.
>
> Thunderbird+outlook gives me the error that the SMTP server is rejecting
> connections and that it cannot connect. Also, Thunderbird+Outlook never
> even prompt me for my password when connecting to the SMTP server. Does
> this mean I am not authenticating, despite it saying I am logging in in
> mail.log?
>
> Note: I tried sending mail with the following SMTP settings:
> No Secure Connection: Port 25
> Secure Connection: Port 25 (TLS), Port 465 (SSL)
>
> Neither will send the mail from Outlook or Thunderbird)
>
> Any help or suggestions are greatly appreciated.
>
>
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> [email protected]
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>

l8*
        -lava (Brian A. Seklecki - Pittsburgh, PA, USA)
               http://www.spiritual-machines.org/

    "Show me a young conservative and I'll show you someone with no heart.
    Show me an old liberal and I'll show you someone with no brains."
    ~ Winston Churchill

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