Help.

I'm new to Sendmail & am trying to set it up to send out a confirmation
email. Should be simple, right? I've done this setup many times in
winworld no problem.

The problem is every mail sent to Yahoo, hotmail & Gmail gets dumped into
the spam folder. I'm really stuck.

Here's the setup:

- confirmation emails sent from the server at the IP address hosting the
domain.
- other mail handled by goDaddy.
- DNS with goDaddy, gdad tech checked DNS setup
- DNSreport from DNSstuff.com looks good
- SPF record done
- host IP address clean, not listed on spam lists
- reverse dns lookup resolves back to the correct domain

Here's a typical hotmail header:

X-Message-Delivery: Vj0zLjQuMDt1cz0wO2k9MDtsPTA7YT0w
X-Message-Status: n:0
X-SID-PRA: T Smith <info [at] mydomain.com>
X-Message-Info:
6sSXyD95QpVIGZjCxpnYA0DdkZvbdqCYlaY6qcr5mNtVA52j7E6MAA0wyUMS ZBIr9JKnPo2lo/U=
Received: from www.mydomain.com ([68.178.98.245]) by
bay0-mc9-f23.bay0.hotmail.com with Microsoft SMTPSVC(6.0.3790.2668);
Mon, 20 Aug 2007 07:20:41 -0700
Received: from www.mydomain.com (localhost [127.0.0.1])
by www.mydomain.com (8.13.8/8.13.8/Debian-3) with ESMTP id l7KEKU4K012294
for <theRecipient [at] hotmail.com>; Mon, 20 Aug 2007 07:20:30 -0700
Received: (from www-data [at] localhost)
by www.mydomain.com (8.13.8/8.13.8/Submit) id l7KEKUK1012293;
Mon, 20 Aug 2007 07:20:30 -0700
Date: Mon, 20 Aug 2007 07:20:30 -0700
To: m anderson <theRecipient [at] hotmail.com>
Subject: Your Dancing Newsletter Confirmation
MIME-Version: 1.0
Content-type: text/html; charset=iso-8859-1
From: T Smith <info [at] mydomain.com>
Reply-To: T Smith <info [at] mydomain.com>
Message-ID: <3046116304489info [at] mydomain.com>
X-Mailer: PHP v5.2.1
Return-Path: info [at] mydomain.com
X-OriginalArrivalTime: 20 Aug 2007 14:20:41.0463 (UTC)
FILETIME=[49D22870:01C7E335]

Whether the message is plain text or html, it still gets dumped to the spam
folder. Spam from "dihydric Park" promising "Curie Erecutilue
Dysfuinctuion" I notice sail right through my hotmail filter however.

I've spent days tweaking the DNS record and the.mc, .cf., .cw, access,
service-switch, sendmail, submit, trusted-users, hosts files etc etc etc
etc. Nothing seems to work.

Help appreciated. Thanks.

M Anderson
Linux Aspirant

Mikal Anderson wrote:

> Received: from www.mydomain.com ([68.178.98.245]) by
^^^^^^^^^^^^^^^
Do you have your Hotmail account (and others you've tested with) perhaps
configured to refile mail as spam if it arrives from a system whose IP
address does not have a PTR record?

> Whether the message is plain text or html, it still gets dumped to the
> spam folder. Spam from "dihydric Park" promising "Curie Erecutilue
> Dysfuinctuion" I notice sail right through my hotmail filter however.

This definitely suggests a problem with the filtering you have setup on
your Hotmail account. I don't see anything particularly "wrong" with
your example message sent with Sendmail, except, as noted above, that
the IP address that Hotmail's mail server received the message from does
not have a PTR record, and you may be filtering and refiling based on
that.

I hope this helps ...

--
------------------------------------------------------------ ----------
Sylvain Robitaille syl [at] alcor.concordia.ca

Systems and Network analyst Concordia University
Instructional & Information Technology Montreal, Quebec, Canada
------------------------------------------------------------ ----------

(adding the comp.mail.sendmail newsgroup back into the discussion, in an
effort to avoid becoming a personal help-desk ...)

On Mon, 20 Aug 2007, Mikal Anderson wrote:

> Filtering on my Yahoo, Gmail and Hotmail accounts are all in their
> default state. I have not touched these settings.

Ok, but that doesn't mean these messages aren't being refiled because of
the lack of the PTR record. You should check whether that's an item
that the default filtering has for these accounts (I don't use any of
these and cannot offer any advice as to whether that is the case, or
where you should check).

> That is not the issue.

I can conclude that you've checked that, then ...

> This issue is that something in my Sendmail setup is causing Yahoo,
> Gmail & Hotmail filter defaults to make a false-positive determination
> that the confirmation email sent from my server is spam. ...

See what DNSBLs are being used by the various email providers:

68.178.98.245 listed by l1.apews.rhsbl.uceprotect.net
68.178.98.245 listed by l2.apews.dnsbl.uceprotect.net
68.178.98.245 listed by test.blocklist.org
68.178.98.245 listed by flowgoaway.com

The headers in the sample message you quoted did not indicate that there
is anything in your Sendmail configuration that would cause the messages
to be misclassified as spam.

> The question then is how do I configure Sendmail so that the mail sent
> to Mr. X does not end up in his spam box?
>
> I'm missing something real basic here. I just can't figure it out.

I don't think you are, at least not based on anything I've seen yet.
Perhaps if you configure your mail software to relay outbound messages
through your ISP's mail server (see SMART_HOST in cf/README for details)
you would avoid messages being misclassified as spam because of the
above DNSBL listings? That would very likely at least avoid the no PTR
record misclassification (which may be happening or not).

I hope this helps ...

--
------------------------------------------------------------ ----------
Sylvain Robitaille syl [at] alcor.concordia.ca

Systems and Network analyst Concordia University
Instructional & Information Technology Montreal, Quebec, Canada
------------------------------------------------------------ ----------