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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 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

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Can you provide a sample email, with headers, that is flagged as spam? –  blueben Jan 3 '11 at 11:13
    
ok... edited the question. –  unmircea Jan 3 '11 at 12:28
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4 Answers 4

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.

share|improve this answer
    
Where do i add SPF records? –  unmircea Jan 6 '11 at 23:08
    
Also, "They all come from me@server.domain.com instead of me@domain.com. I must be missing an alias somewhere." Make sure domain.com is set up as the domain name and host name in Server Admin under the Mail service, not server.domain.com. –  Jack Lawrence Jan 11 '11 at 21:38
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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.

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Is this one any good: v=spf1amx~all. How do i add one? SPF is not mentioned in the server setup book. Is this some kind of standard, because if it is it's not very well documented. –  unmircea Jan 3 '11 at 14:15
    
Hmm... first time i heard of SPF in my life... My server setup book makes no mention of them. –  unmircea Jan 3 '11 at 15:29
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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.

share|improve this answer
    
In my dns i have an A record with @ pointing my IP, blank record pointing to my IP, then another A record SERVER pointing to my IP again and two or three Aliases CNAME records pointing to SERVER. –  unmircea Jan 3 '11 at 14:04
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This question gets asked frequently here - read some of the previous responses. Note there is no magic bullet fix.

share|improve this answer
    
I understand... i think it's the naming issue. All my emails seem to come from @www.domain.com instead of just @domain.com. Can this be fixed? –  unmircea Jan 3 '11 at 13:13
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