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Asked: 2011-01-04 02:00:48 +0800 CST

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

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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 [email protected] instead of [email protected]. 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: [email protected]

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 [email protected]) 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 [email protected]) [email protected]

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: [email protected]

To: [email protected]

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

mac-osx-server spam email-server

4 Answers

  1. 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.

    • 1

  2. I work for a Google partner, so I may be able to help.

    • Do the emails go to spam for a Live Mail account? (Out of curiosity)
    • Is this to a Google Apps account, or Gmail.com account?
    • Does it happen on other Gmail accounts?

    Do your A records contain WWW in them?

    Edit: As suggested below, SPF is also very important, I'd assumed you'd have these.

    • 0

  3. As a first guess, you should probably set up the right SPF recors in your DNS for your domain. Currently it seems there are no entries, therefore simply add one allowing only your mail server to send mails for your domain.

    • 0

  4. This question gets asked frequently here - read some of the previous responses. Note there is no magic bullet fix.

    • -1