My mail server flagged spam!

[Robert Bonomi]

> From owner-freebsd-questions at freebsd.org  Sat Oct 23 17:45:25 2010
> From: Marwan Sultan <dead_line at hotmail.com>
> To: <m.seaman at infracaninophile.co.uk>
> Date: Sat, 23 Oct 2010 22:46:40 +0000
> Cc: FreeBSD Questions <freebsd-questions at freebsd.org>
> Subject: RE: My mail server flagged spam!
>
>
> Dear Dr. Matthew.=2C
> =20
>    When my client or any clients uses the web mail that i have configured=
> =2C=20
>    then everything works fine NO spam problems and email will be
>    received by hotmail=2C gmail and vise versa.
> =20
>    I found out that this particular client complaining because they use
>    outlook express NOT the web mail.
> =20
>    they configure their outlook express to use SMTP user/password
>    with mail.clinet_domain.com as incoming/outgoing.
> =20
>   even if they send from xyz at client_domain to admin at MyDomain.com
>   both are in same server=2C I will still receive it as SPAM.
>   (They are sending from outlook.)
> =20
>   looking at spam log=2C and why its scored as spam.. here is a copy.
> =20
> pts rule name              description=20
> ---- ---------------------- -----------------------------------------------=
> ---=20
> 0.9 RCVD_IN_PBL            RBL: Received via a relay in Spamhaus PBL=20
>                            [95.66.68.100 listed in zen.spamhaus.org]=20
> 0.0 HTML_MESSAGE           BODY: HTML included in message=20
> 0.0 BAYES_50               BODY: Bayesian spam probability is 40 to 60%=20
>                            [score: 0.5019]=20
> 2.2 TVD_SPACE_RATIO        BODY: TVD_SPACE_RATIO=20
> 0.1 RDNS_NONE              Delivered to trusted network by a host with no r=
> DNS=20
> 2.8 DOS_OE_TO_MX           Delivered direct to MX with OE headers=20
> =20
> =20
> As you see 2.8 for DOS_OE_TO_MX
> and 2.2 for TVD_SPACE_RATIO
> =20
>  I have looked for DOS_OE_TO_MX
>  and it says because client is sending "directly" to MX records?
>  well! i asked them to use "mail.server_name.com" for income/outgoing
>  for outlook express..but still the same error and email is scored as spam.
> =20
>  Any help is highly appreciate it.


lots of stuff is mis-configured.

If you have people outside your network addresses trying to send mail 
through your server, you need to be running a 'mail submission agent'
on port 587, as well as the MTA on port 25.  If you're not doing this
already, you'll have to set it up.  Since this access is password
protected, and available only to your 'trusted' users, it does -not-
need spam-filtering on it. (usually, that is -- you know your customers
better than we do :)

*AND* the client using Outlook Express needs to configure _it_ to use your
server *on*port*587* as the 'outgoing mail server'.

This will require entering 'authentication' information (username and
password) into Outlook Express.