I'm sending this message with Geary but I have changed the configuration.

On Wed, Jul 16, 2014 at 11:37 AM, Chris Knadle <[email protected]> wrote:
On Wednesday, July 16, 2014 10:56:06 Aram J. Agajanian wrote:
I sent the last message with Geary and something about it seems to have
 triggered the spam filter.

1.  Invalid timezone in the Date: field:

       Date: Wed, 16 Jul 2014 01:57:33 -0004

    that "-0004" isn't a valid timezone.  As you're in New York, that
    should be "-0400".

      2.0 point spam score for this.

This seems like a bug in Geary.  I'll look for a bug report.


2. Sending the mail via an IP address owned by optonline.net directly, and optonline.net has an SPF record listing who can send email from that
    domain, and naturally the IP address used isn't in that list.
      0.7 point spam score for this.

Furthermore the IP address on optonline.net is listed in the SpamHaus PBL list as one that shouldn't be sending unauthenticated email directly
    (because it's a dynamic IP address on an ISP connection):
        http://www.spamhaus.org/pbl/
      3.6 point spam score for this.

And IP address used has a reverse DNS lookup that looks like a dynamic
    IP address (because it is)...
      0.4 point spam score for that.

    Total: 4.7 points for sending email from a dynamic IP address on
           optonline.net directly

I've been routing my outgoing mail through Postfix for years. I haven't detected a problem before this. I just changed the configuration to no longer use Postfix.

I'll miss Postfix's logging but I guess that I can use Wireshark instead.


.

3. The HELO/EHLO used in the SMTP session to send the mail is invalid:

       Received: from server.localdomain

For Postfix this is usually set in /etc/mailname on Debian-based systems,
    or defaults to the FQDN used on the box on other systems.

Surprisingly, SpamAssassin didn't add a score for this, but it probably
    should have.

Well, I believe that all SMTP clients have to HELO or EHLO. Since most won't have a DNS-registered hostname, it's probably a good idea that it doesn't indicate spam.



The bottom line is:

- there are a few things in your setup that you can fix that would bring
     you just below the 5.0 threshold

- you need to relay your mail through a "real mail server" somewhere if
     you want to be able to relay mail reliably.

I was relaying through Optimum's mail server. The problem seems to be that there was an MTA sending from an blacklisted IP address anywhere in the path.

                                                        Aram



  -- Chris

--

Chris Knadle
[email protected]

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