On Thursday, July 17, 2014 03:23:26 Aram J. Agajanian wrote:
> 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.

Yes that sounds right.

> > 2.  Sending the mail via an IP address owned by 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.

I don't think using Postfix was part of the problem, and in fact
I'd suggest switching back to using it but using a valid EHLO/HELO.

Have a look at the "myorigin =" and "myhostname =" settings in the main.cf 
file.

> > 3.  The HELO/EHLO used in the SMTP session to send the mail is
> > invalid:
[...]
> Well, I believe that all SMTP clients have to HELO or EHLO.

Yes, that's mandatory for any SMTP session.

> Since most won't have a DNS-registered hostname, it's probably a good
> idea that it doesn't indicate spam.

Yes, but server.localdomain is not a valid FQDN.  RFC 5321 is specific that 
the EHLO/HELO must either be a FQDN, or an "address literal", meaning the 
sending IP address in []'s.  e.g. [67.82.156.119] :

  2.3.5.  Domain Names
  [...]
    o  The domain name given in the EHLO command MUST be either a primary
          host name (a domain name that resolves to an address RR) or, if
          the host has no name, an address literal, as described in
          Section 4.1.3 and discussed further in the EHLO discussion of
          Section 4.1.4.

In the 2nd message you sent that got tagged as spam, the headers show that 
you've got a dyndns.org DNS address -- you could use /that/ DNS address as the 
EHLO/HELO for Postfix -- that would be valid.  Likewise, your 1st message that 
got tagged send the mail using a EHLO/HELO of an internal IP [192.168.x.x] 
which is also valid -- if you could configure Postfix to do the same thing, 
that would also work.

> > 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.

You're right -- my apologies.  mta6.srv.hcvlny.cv.net  didn't look like an 
optonline.net mail server to me...  I keep forgetting that the cv.net domain 
is also optimum online.

> The problem seems to be that there was an MTA sending from an blacklisted
> IP address anywherein the path.

My experience has been that this isn't usually a problem as long as one uses a 
correct EHLO/HELO in each "mail hop", but it is a problem if not.

  -- Chris

--

Chris Knadle
[email protected]
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