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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