Resolved my Mail Server Issue:

[rick]

In case anyone is interested...

Email sent from my mail server has been flagged immediately as spam when trying to join forums such as this one :nolike:
Luckily, Jordan manually enabled my account after an email questioning the rejection due to spam.

SETUP:
Linux VPS server: (RickDavis.org)
Email Transfer Agent: Postfix
IMAP Server: Dovecot
Web App: Squirrelmail

DNS CNAME Sub-domain record: mail.rickdavis.org
DNS MX record: rickdavis.org

Just the other day, I was inspecting the header coming from my domain email server and noticed the following...
(just showing the important lines)
---------------------------------------------------------------------
Received: from rickdavis.org ([-my ip address-])
-- blah blah
Received: from mail.rickdavis.org (localhost [127.0.0.1])

by rickdavis.org (Postfix) with ESMTP id​

-- blah blah
Received: from -- ip address --

(SquirrelMail authenticated user register)
by mail.rickdavis.org with HTTP:​

-- blah blah
-----------------------------------------------------------------------

Apparently IMHO, spam detection was triggered due to the different names: mail.rickdavis.org and rickdavis.org
As this was a transfer agent issue, I modified my /etc/postfix/main.cf file and changed
myhostname = rickdavis.org to myhostname = mail.rickdavis.org
haven't been flagged as spam since. :thumbsup:

The confusing thing is...
I assumed that I should populate the Postfix myhostname parameter with the DNS MX record,
but apparently this is a problem when running Squirrelmail from the mail.rickdavis.org DNS CNAME sub-domain.
After changing myhostname = mail.rickdavis.org all references in my email headers match (mail.rickdavis.org)

I don't know how it all works, but it appears to be fixed now.

Hope this helps someone else going through the same thing.

 

[Jordan]

Glad to see you resolved the issue
Fortunately though, you had contacted us in regards to membership. Some people just go on about their business if they get flagged as spam and we loose a potential member of the forum

 

[xpl0iter]

Thanks for explaining how you resolved your issue. It will help other people who have come across this issue!
I have never experienced this issue with my VPSs, so I am wondering why it happened for you! :O

 

[rick]

I have never experienced this issue with my VPSs, so I am wondering why it happened for you! :O

That's easy, because I have "the luck" :wtf: , sometimes things just happen to me.

I'm sure I caused it by configuring Postfix using the TLD, and running Squirrelmail from the subdomain defined via DNS.
One or the other, not both. Actually email worked just fine, but spam filters kept beating me down. :beatup:

Live and Learn I guess