Mail sent from Zimbra server going to spam on yahoo

[sundru]

Hi guys,

I was wondering if anyone had gone thru this issue, mail sent from the zimbra server ends up in the spam folder on yahoo only. It works correctly in gmail and hotmail ..

have attached the headers from mail sent from gmail and a zimbra servers to a yahoo account.

Header sent from gmail

From zimbrauser Wed Mar 12 08:32:25 2008
Return-Path: <zimbrauser@gmail.com>
Authentication-Results: mta189.mail.re2.yahoo.com from=gmail.com; domainkeys=pass (ok)
Received: from 209.85.200.172 (EHLO wf-out-1314.google.com) (209.85.200.172)
by mta189.mail.re2.yahoo.com with SMTP; Wed, 12 Mar 2008 08:32:26 -0700
Received: by wf-out-1314.google.com with SMTP id 28so2998982wff.4
for <xxxx_xxxx@yahoo.com>; Wed, 12 Mar 2008 08:32:25 -0700 (PDT)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
d=gmail.com; s=gamma;
h=domainkey-signature:received:received:message-id:date:from:to:subject:mime-version:content-type;
bh=bspr/mkXJWQEZGiA+H8wQ0poqI+LKnDemwFNgs3fIyI=;
b=Dn8nzF6Zu/4dskaV/SuyWCAb29SQfN5FduheTaFLN55f0aWmdMkmx2mgMBSpg1UggtN 3gCBj8qjuxJgxh96GkdUntPJ9Hjm5fDjRY0eJI1HlBxV3arcvL b0bloOtQVW3P/rpSoe1t9jfgxkyuP3eVqGHDq8THjKlj3cDoZDl8gw=
DomainKey-Signature: a=rsa-sha1; c=nofws;
d=gmail.com; s=gamma;
h=message-id:date:from:to:subject:mime-version:content-type;
b=j5l2Sv0FGYF1FFU6O5tlEyLoFydZH+ACu4msW+AS6Qb8CT0A R/s9KIRem9vgVm35OSfu6gL/NAcn1qKxu0OGJdZe5krjcVkTJ0LHxAdlGTuFsqF3bNcMCxqc2f cgaqxvv1GhDZl3rOo9x4Y5GwdC1KpH0nb1/IuWzpMPjoSRU/o=
Received: by 10.142.215.5 with SMTP id n5mr3514776wfg.11.1205335945280;
Wed, 12 Mar 2008 08:32:25 -0700 (PDT)
Received: by 10.142.191.16 with HTTP; Wed, 12 Mar 2008 08:32:25 -0700 (PDT)
Message-ID: <d1216c0c0803120832qc574e43rb6253ea3e9da7ded@mail. gmail.com>
Date: Wed, 12 Mar 2008 11:32:25 -0400
From: zimbrauser <zimbrauser@gmail.com>
To: xxxx_xxxx@yahoo.com
Subject: test email
MIME-Version: 1.0
Content-Type: multipart/alternative;
boundary="----=_Part_6954_23340243.1205335945262"
Content-Length: 742

Header sent from Zimbra server

From zimbrauser Wed Mar 12 08:26:08 2008
Return-Path: <supa@hyperdryve.com>
Authentication-Results: mta160.mail.re4.yahoo.com from=hyperdryve.com; domainkeys=neutral (no sig)
Received: from xx.xxx.xxx.xx (EHLO zimbra.server.com) (xx.xxx.xxx.xx)
by mta160.mail.re4.yahoo.com with SMTP; Wed, 12 Mar 2008 08:26:14 -0700
Received: from localhost (localhost [127.0.0.1])
by zimbra.server.com (Postfix) with ESMTP id 8849D18E0304;
Wed, 12 Mar 2008 11:26:13 -0400 (EDT)
tests=[BAYES_40=-0.185, RCVD_IN_XBL=3.033, RDNS_NONE=0.1,
SUSPICIOUS_RECIPS=2.912]
Received: from zimbra.server.com ([127.0.0.1])
by localhost (zimbra.server.com [127.0.0.1]) (amavisd-new, port 10024)
with ESMTP id RxVM04DcYCRn; Wed, 12 Mar 2008 11:26:08 -0400 (EDT)
Received: from zimbra.server.com (zimbra.server.com [xx.xxx.xxx.xx])
by zimbra.server.com (Postfix) with ESMTP id 94D5218E02FC;
Wed, 12 Mar 2008 11:26:08 -0400 (EDT)
Date: Wed, 12 Mar 2008 11:26:08 -0400 (EDT)
From: zimbrauser <supa@hyperdryve.com>
To: xxxx_xxxx@yahoo.com
Message-ID: <32402905.7941205335568294.JavaMail.root@zaphod>
Subject: another test email to check reverse dns fixed issue
MIME-Version: 1.0
Content-Type: text/plain; charset=utf-8
Content-Transfer-Encoding: 7bit
Content-Length: 53

[uxbod]

Hmmm, this does not look good RCVD_IN_XBL=3.033.

Put your external IP address into The Spamhaus Project - XBL

[dwmtractor]

This one doesn't help you either:

SUSPICIOUS_RECIPS=2.912

According to Spamassassin, this one is the result of "Similar addresses in recipient list" which, if I understand it correctly, would have to mean you're sending the message to multiple recipients and it looks too much like a dictionary list that the spammers would use. Was this a message to multiple recipients?

Not to cast aspersions, but sometimes people (and I'm not saying you're one of them) get caught in spam filters because their messages look too much like spam. . . We all have to learn how to build a good email message.

I should warn you that one other thing which will result in getting classified as spam by Yahoo!, and this one is not as obvious in the headers, is if your messages are being sent out by a different IP address than the one in your public MX record. This can happen if you have your mailserver on a DMZ behind a firewall, and you route your email traffic to a secondary IP and not the primary gateway IP of the firewall. I explain this issue in more detail in this post.

Cheers,

Dan

[uxbod]

Also, if you are on some sort of *DSL/Cable connection it is advisable to relay through your ISP instead of sending direct.

[sundru]

Great thx guys ! I was thinking it may be due to this , since somehow the sender identifies itself as localhost.

Received: from localhost (localhost [127.0.0.1]) , while on gmail its something else.

[dwmtractor]

Originally Posted by uxbod

Also, if you are on some sort of *DSL/Cable connection it is advisable to relay through your ISP instead of sending direct.

Presuming your ISP will permit it. This can be a royal pain if your ISP (or other domain hosting provider) is, like mine, stuck on POP-before-SMTP as the only acceptable authentication method.

[sundru]

follow up on the previous post i assume that yahoo does some kind of reverse dns lookup to validate email ..

[sundru]

we are on a business FIOS and a redundant T1 line , and am pretty sure nothings blocked.

[sundru]

I just checked the spamhaus and the ips not on the list. So not sure why still heading to spam .. or why yahoo tagging it that way .

[dwmtractor]

Originally Posted by sundru

Great thx guys ! I was thinking it may be due to this , since somehow the sender identifies itself as localhost.

Received: from localhost (localhost [127.0.0.1]) , while on gmail its something else.

That "localhost" part isn't going away. That's the part of the header that happens (and always will) if you send mail from your webclient. It's Postfix saying that it got the message first from the local Zimbra box before relaying it on.

The problem isn't at that step. It's this one:

Received: from xx.xxx.xxx.xx (EHLO zimbra.server.com) (xx.xxx.xxx.xx)
by mta160.mail.re4.yahoo.com with SMTP; Wed, 12 Mar 2008 08:26:14 -0700

That ip address you suppressed--is it the SAME ip address we'd get if we were to dig or mxlookup your domain? If it is not, that will result in Yahoo calling your message junk. . .at least it did for me.