New Mac OS X Server setup, when i send mail to gmail it goes straight to Spam. Why is that

email-servermac-osx-serverspam

New Mac OS X Server setup, when i send mail to gmail it goes straight to Spam. Why is that?

My setup:
DNS – done (A records PTR are ok)
Mail Setup – done
Webmail – done

Also there seems to be a naming problem. They all come from me@server.domain.com instead of me@domain.com. I must be missing an alias somewhere.

I've read an entire book on setting this up so don't throw stones 🙂
The GUI is masking a lot of this up for me, so explanations via GUI are appreciated.

The headers look like this:

Delivered-To: MYACCOUNT@gmail.com

Received: by 10.142.252.19 with SMTP id z19cs476033wfh;

    Mon, 3 Jan 2011 01:37:09 -0800 (PST)

Received: by 10.204.64.208 with SMTP id f16mr8853543bki.61.1294047428115;

    Mon, 03 Jan 2011 01:37:08 -0800 (PST)

Return-Path:

Received: from server.DOMAIN.com ([94.x.x.x])

    by mx.google.com with ESMTP id c20si50831332bkc.48.2011.01.03.01.37.07;

    Mon, 03 Jan 2011 01:37:07 -0800 (PST)

Received-SPF: neutral (google.com: 94.x.x.x is neither permitted nor denied by best guess record for domain of USER@www.DOMAIN.com) client-ip=94.x.x.x;

Authentication-Results: mx.google.com; spf=neutral (google.com: 94.x.x.x is neither permitted nor denied by best guess record for domain of USER@www.DOMAIN.com) smtp.mail=USER@www.DOMAIN.com

Received: from localhost (localhost [127.0.0.1])

by server.DOMAIN.com (Postfix) with ESMTP id 0A19F60508;

Mon,  3 Jan 2011 11:37:07 +0200 (EET)

X-Virus-Scanned: amavisd-new at DOMAIN.com

Received: from server.DOMAIN.com ([127.0.0.1])

by localhost (server.DOMAIN.com [127.0.0.1]) (amavisd-new, port 10024)

with ESMTP id mNgNTNwNhyP1; Mon,  3 Jan 2011 11:37:06 +0200 (EET)

Received: from www.DOMAIN.com (localhost [127.0.0.1])

by server.DOMAIN.com (Postfix) with ESMTP id 57E69604F1;

Mon,  3 Jan 2011 11:37:06 +0200 (EET)

Received: from 10.0.1.3

    (SquirrelMail authenticated user USER)

    by www.DOMAIN.com with HTTP;

    Mon, 3 Jan 2011 11:37:06 +0200

Message-ID:

Date: Mon, 3 Jan 2011 11:37:06 +0200

Subject: test

From: USER@www.DOMAIN.com

To: MYACCOUNT@gmail.com

User-Agent: SquirrelMail/1.4.20

MIME-Version: 1.0

Content-Type: text/plain;charset=iso-8859-1

Content-Transfer-Encoding: 8bit

X-Priority: 3 (Normal)

Importance: Normal

test

Best Answer

SPF records and reverse DNS for the mail server IP address will help a lot for getting mail through to Google.

Check out mxtoolbox.com for some helpful mail server IP tests and setup.

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