Mail sendt from my mailserver to Yhaoo.com, Hotmail.com, Gmail.com all end up in spam folder

I have a common problem iguess... when sending mail to Yhaoo.com, Hotmail.com Gmail.com from my mail server(MailEnable 3.10) it all ends up in the spam/junk/bulk folder. Sending mail to rest of the world works fine.

My setup;
I do have a valid PTR record (same as A record)
My IP is not listet in the Spam Database Lookup http://www.dnsstuff.com/tools/ip4r.ch?ip=213.180.86.192
I only allow SMTP relay for authenticated users
I have tested from both my webmail service and from my outlook client, same result...
I have also tested with two different IPs

But still its not working... I'm pretty close to throwing something out the window...

------------- Mail header of mail sent from my troublesome server getting stopped ----------------
From Kim Egenes Fri Feb  8 06:13:44 2008
Return-Path: <kim@webkiosk.no>
Authentication-Results: mta115.mail.re4.yahoo.com  from=webkiosk.no; domainkeys=neutral (no sig)
Received: from 213.180.86.192  (EHLO webkiosk.no) (213.180.86.192)
  by mta115.mail.re4.yahoo.com with SMTP; Fri, 08 Feb 2008 06:13:48 -0800
Received: from ([158.36.103.20]) by webkiosk.no with MailEnable WebMail; Fri, 8 Feb 2008 15:13:44 +0100
To: <kimegenes@yahoo.com>
From: "Kim Egenes" <kim@webkiosk.no>
Subject: Hello there
Date: Fri, 8 Feb 2008 15:13:44 +0100
Message-ID: <5E05244D9EEA4A68A5F901E58BC552F1.MAI@webkiosk.no>
MIME-Version: 1.0
Content-Type: multipart/mixed;
      boundary="--=_Part_6EA993954EBC4E65918CDB4DD8321423"
Content-Length: 257


------------- Mail header of mail sent from my workmail getting through to yahoo.com ----------------
From Egenes Kim Fri Feb  8 06:19:09 2008
Return-Path: <kim.egenes@veths.no>
Authentication-Results: mta515.mail.mud.yahoo.com  from=veths.no; domainkeys=neutral (no sig)
Received: from 158.36.103.101  (EHLO mailscanner2.veths.no) (158.36.103.101)
  by mta515.mail.mud.yahoo.com with SMTP; Fri, 08 Feb 2008 06:19:43 -0800
Received: from nvhmail.veths.no (nvhmail.veths.no [10.77.17.50])
      by mailscanner2.veths.no (Symantec Mail Security) with ESMTP id 878CC2020F
      for <kimegenes@yahoo.com>; Fri,  8 Feb 2008 15:23:16 +0100 (CET)
Content-class: urn:content-classes:message
MIME-Version: 1.0
Content-Type: multipart/alternative;
      boundary="----_=_NextPart_001_01C86A5D.927E60A9"
Subject: test from work
Date: Fri, 8 Feb 2008 15:19:09 +0100
Message-ID: <F307A63E90E63248B917DF4AF877988D385164@nvhmail.veths.no>
Thread-Topic: test from work
Thread-Index: AchqXZKSe7MqAZ90SySxUDgowarWaQ==
From: "Egenes Kim" <Kim.Egenes@veths.no>
To: <kimegenes@yahoo.com>
Content-Length: 2271

Thanks
Kim
NVH-itAsked:
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grbladesCommented:
Can you send me an email. I have a test address listed in my profile. It may flag up something.
Please post here when the email has been sent.
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Syngin9Commented:
I was running into the same problem with my Qmail servers.  

You will want to set up SPF and DomainKeys(if available for your email server software).

Further reading:

SPF: http://www.openspf.org/

Its pretty easy to enable as all it requires is an additional DNS TXT record to be added that designates the ips that are allowed to relay email for your domain.  As such, its easy to set up regardless of what email server software you are running.

If you have access to your DNS and have a list of all mail server ips for the domain in question, I can help you write out your SPF record.

DomainKeys: http://domainkeys.sourceforge.net/

This might be a little trickier for you to to implement as it requires its own DNS entry, an additional encryption library installed on the server, and the email server configured to sign outgoing email which is then checked against a public key embedded in the aformentioned DNS entry.

Yahoo in particular is a stickler for DomainKeys since it was the company that developed the technology.

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Syngin9Commented:
Actually, in the header you posted, you can see the check Yahoo is making for DomainKeys:

domainkeys=neutral (no sig)
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Syngin9Commented:
I haven't used Amavis before but its serves an identical purpose to Qmail-Scanner which I use all the time on my Debian Mail servers (ie. adds the ability to tie multiple mail scanners into the MTA) and I actually have a cron job that empties out my quarantine folder once a week.

To be on the safe side though, have a look for the following line in /etc/amavis/amavisd.conf:

$QUARANTINEDIR = '/var/lib/amavis/virusmails';

It should exist and, if it does, you should safely be able to empty out the contents of that directory (don't remove the directory itself though)  If for some reason, the directory has too many files in it to remove with the rm command, you may have to actually remove the directory to get rid of them all.  Just remember to make a note of the ownership and permissions on the directory so you can recreate it afterwards.
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Syngin9Commented:
Ouch, sorry, I typed the solution to another post in this thread by mistake.  Please ignore the above post.
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NVH-itAuthor Commented:
grblades:
Sent you a testmail with Subject "Hello from Kim", thanks

Syngin9:
Yes it looks like Yahoo is doing a test for domainkeys=neutral (no sig) guess this is SPF. The domainkeys=neutral (no sig) is present in the mail that got through as well... maybe adding an SPF will tip the scale in my favour.

I'm starting to suspect that my IPs is blacklisted. I just got my dedicated server with 3 ips, maybe this IP range are blacklisted internally at yahoo, gmail and hotmail? Sounds a bit far fetched though....

Kim
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NVH-itAuthor Commented:
Is there any chance that the problem could boil down to the specific brand of MailServer(MailEnable) that I'm using?

Kim
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grbladesCommented:
You are not on any RBLs (blacklisted)
There is no problem with your DNS configuration.
There is nothing wrong with the content of the mail itself.

I would recomend that you implement SPF (easy) and DKIM (the new name for domainkeys).
You can also register your IP address with http://www.dnswl.org/

So to clarify there is nothing wrong with your setup which should cause you to be penalised in terms of a spam score.
However you are not doing anything to help stop people spamming pretending to be you and this is where SPF, DKIM and dnswl come in.
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Syngin9Commented:
One thing to note is whether your DNS provider offered TXT record service.  Network Solutions doesn't.  I had to switch registrars to be able to use it.  If you run your own DNS server, you'll be all set though.

You'd need this functionality for both SPF and DomainKeys

Sample SPF record that allows for only 2 ips to send email for the domain:

@ IN TXT 'v=spf1 ip4:x.x.x.x ip4:y.y.y.y -all'
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NVH-itAuthor Commented:
Hi guys
Just an update for those who might be interested. I have been busy researching my troubles and as a last desperate resort i sent an email to Hotmail Support, never expecting an answer... But they actually responded;
"Hello Kim,
Thank you for your patience as we researched your issue. I am pleased to inform you that we have taken steps to implement a temporary mitigation to your mail delivery problem.  The mitigation will take 24-48 hours to fully reflect in our system."

Did a test and it worked instantly :) just hope it sticks since they mentioned the word "temporary"...

When I first started sending mails to hotmail without SPF implementet all my mail landed in the junk folder. When I eventually Implemented SPF, Hotmail just rejected all my mails, they never showed up anywhere. There was a funny incident at one stage when I sent a test mail, as expected my mail hit the junk folder... I then checked my inbox and discovered that a spam mail with "Viagra" in the subject field had been let through but my innocent test mail had been blocked, whatta h.... They clearly have issues...

Used resources;
Link to Hotmail Support form
https://support.msn.com/eform.aspx?productKey=edfsmsbl&ct=eformts

SPF Wizard, this one worked best for me.
http://www.microsoft.com/mscorp/safety/content/technologies/senderid/wizard/

Now I have to do the same rutine with Gmail... Anybody now how to easily contact Gmail support?
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