[Pkg-exim4-users] Problem with exim4 and Outlook 2003 when sending emails

[Liviu Tudor]

Hi everyone,

	I hope somehow that you get the type of question that I'm about to
ask quite often (and therefore able to point me immediately to a resource on
the web which will help me solve it) and it's just me who has been searching
using the wrong terms and therefore not finding an answer to this question
-- as I have posted this question on a few forums and spent a couple of
weeks searching for a solution and got nowhere :(
	So, in brief, I'm using exim4 on a Debian Linux system (more
specifically the exim4-daemon-heavy package) and I am trying to get this
thing to work with MS Outlook 2003 (note that I am talking about "Outlook"
and not Outlook Express -- in other words, the Outlook that is part of MS
Office 2k3). I'm using Courier IMAP SSL to read emails with a self generated
certificate and that strangely enough works fine in Outlook (well I had to
do a little bit of configuration on courier side but nothing major).
However, the problem arrives when I'm trying to use Outlook to SEND emails! 
	Before I start explaining what's what, I must point out that having
read about various quirks in MS Outlook 2k3 SMTP implementation, I have
decided to test the configuration with another email client as well so I
have also installed and configured and tried Thunderbird -- which works fine
(for both sending and receiving emails) so it looks like the config is ok
but I'm just guessing I'm just missing that extra configuration line that
reads something like "fixoutlook2003 = 1" :)
	Right, so, what I have tried to achieve is the following: have exim
accept email normally for my domain (say example.com) and obviously prevent
open relaying -- so unless the email is intended for a user in the domain
example.com then the user will have to be authenticated. Now that is very
easily configured (in fact it's present by default) in
/etc/exim4/conf.d/acl/... (I use a split file configuration). In order to
enable TLS (on port 465) I have the following in my
/etc/exim4/conf.d/main/000_localmacros:
 
daemon_smtp_ports = 25 : 465
tls_on_connect_ports = 465
AUTH_CLIENT_ALLOW_NOTLS_PASSWORDS = 0
MAIN_TLS_ENABLE = true

In terms of authenticators I've only got 2 set up:
plain_server:
   driver = plaintext
   public_name = PLAIN
   server_condition = "${if
crypteq{$auth3}{${extract{1}{:}{${lookup{$auth2}lsearch{CONFDIR/passwd}
{$value}{*:*}}}}}{1}{0}}"
   server_set_id = $auth2
   server_prompts = :
   .ifndef AUTH_SERVER_ALLOW_NOTLS_PASSWORDS
   server_advertise_condition = ${if eq{$tls_cipher}{}{}{*}}
   .endif


cram_md5_server:
   driver = cram_md5
   public_name = CRAM-MD5
   server_secret =
${extract{2}{:}{${lookup{$auth1}lsearch{CONFDIR/passwd}{$value}fail}}}
   server_set_id = $auth1


(all the others have been commented out)


Now as I said, this configuration works just fine with the likes of
Thunderbird (which is configured to authenticate both at receive and send
email) and my messages are sent just fine. In outlook though, I can only
receive emails and any time I try to reply to any emails received (or simply
just send a new email) exim throws an error about relaying not being
allowed. Which basically says to me that Outlook is not sending the
authenticating at all when sending emails.

As I said before, I've posted this question on a few forums (even asked my
ISP -- and they were useless at fixing this!) so I decided in the end to
post it on this group as I'm sure someone else must have come across
something similar and hopefully found a way to fix it.
Any help in this is greatly appreciated.
Regards,


Liviu Tudor