Re: Configuring Postfix to Receive Mail from Outlook Express 6.0 Outlook 2003

2 msg	MASQUERADING FROM BUT NOT TO
3 msg	Probably not a Postfix problem...?
3 msg	Quick question with user/virtual aliases.
4 msg	Sending healty batch emails
5 msg	use of relayhost, relaydomain?
6 msg	naming the mail server
1 msg	Re: statistics by client ip address - SOLVED
3 msg	question marks on permissions/owner

Configuring Postfix to Receive Mail from Outloo...
\ Jason Hirsh (14 Mar 2008)
. \ Mihira Fernando (16 Mar 2008)

3 msg	tcp_table and propose for new lookup table 'pip...
12 msg	About date spoofing
3 msg	Overriding DNS lookups for a specific domain
2 msg	redirecting a single email address/alias (not a...
1 msg	statistics by client ip address
2 msg	sender+ip restrictions
14 msg	postfix-2.5 RPMs available
1 msg	Setting up Postfix on Solaris 10
8 msg	Yet another virtual domain problem - do not lis...
2 msg	getting a user permissions error
2 msg	551 mail refused

Subject:	Re: Configuring Postfix to Receive Mail from Outlook Express 6.0 Outlook 2003
Group:	Postfix-users
From:	Mihira Fernando
Date:	16 Mar 2008

On Fri, 14 Mar 2008 10:17:37 -0400
Jason Hirsh <hirshj> wrote:

> I am not a real experience postfix user but have muddled through
>
> This one has me stuck...
>
> I have a Postfix/Dovecot installation on FreeBsd 6.1
>
> I have TLS/SSL working using pop3/imap and smtp (110/143/25 and
> 2500)
>
> I believe for outlook i have to enable smtps
>
> I added the following to Master.cf
>
> smtps inet n - n - - smtpd -v
> -o smtpd_tls_wrappermode=yes
> -o smtpd_sasl_auth_enable=yes
>
> Reloaded postfix
>
> openssl s_client -connect localhost:465
>
> shows normal operation
> quote
> CONNECTED(00000003)
> depth=1 /O=Root CA/OU=http://www.cacert.org/CN=CA Cert Signing
> Authority/emailAddress=support
> verify error:num=19:self signed certificate in certificate chain
> verify return:0
> ---
> Certificate chain
> stuff omitted
> No client certificate CA names sent
> ---
> SSL handshake has read 3572 bytes and written 340 bytes
> ---
> New, TLSv1/SSLv3, Cipher is DHE-RSA-AES256-SHA
> Server public key is 1024 bit
> SSL-Session:
> Protocol : TLSv1
> Cipher : DHE-RSA-AES256-SHA
> Session-ID:
> 313873011796FC5A5A44E8EDB6CA19482C3CB7329CD0974D95C5A1E5C0BEAA51
> Session-ID-ctx:
> Master-Key:
> Key-Arg : None
> Start Time: 1205503050
> Timeout : 300 (sec)
> Verify return code: 19 (self signed certificate in certificate
> chain)
> ---
> 220 Hi This is the Ocean Window - BV
> end quote
>
> when I telnet externally to 465 I do not get Helo
>
> when I use outlook
>
> I get various error message and error number 0x800CCC79 BUT
> my maillog server shows no activity
>
> of interest thunderbird if I check ssl instead of TLS on port 465 has
>
> no problem
>
>
> /etc/services does reflect smtps 465/tcp and smtps 465/udp
>
> I am no outgoing blocks on port 465 and am not running a firewall on
> the server
>
> Anyone have an idea what I messed up???

see here :
http://www.awebhosting.com/help/outlook_xp/errors.html#e5

it would appear that Outlook has not tried to authenticate itself.
Check the SMTP authentication settings in outlook and also if Postfix
allows broken clients to authenticate in the main.cf:
broken_sasl_auth_clients = yes

Mihira.
--
"Not many people know when love really starts...
More than a friend, but not quite lovers.
A delicate relationship like this changes gradually once it is noticed,
and keeps on blossoming, Just like the changing seasons."
-- Kanzaki Kyoichi