Question

Email sent to gmail is flagged as spam.

Posted December 11, 2013 73.2k views
I am almost ready to give up here. I have a ubuntu server with postfix and I am hosting mutiple domain names with email accounts. Any email address I send from on my server to gmail ends up in a spam folder. I have this SPF record set for all my domains in the DNS and my email still ends up in gmails spam folder. Here is my SPF record: @ v=spf1 mx ip4:192.241.174.155 -all I have checked the spam lists from here http://www.spamhaus.org/query/ip/192.241.174.155 and everything looks good. Any help would be appreciated. I am at a loss. Here is a email header from one email that is put in apm folder Delivered-To: blah@gmail.com Received: by 10.68.204.97 with SMTP id kx1csp344035pbc; Wed, 11 Dec 2013 15:41:50 -0800 (PST) X-Received: by 10.224.55.197 with SMTP id v5mr6990173qag.9.1386805309858; Wed, 11 Dec 2013 15:41:49 -0800 (PST) Return-Path: Received: from blahtech.us (blahtech.us. [192.241.174.155]) by mx.google.com with ESMTP id t13si17143153qef.73.2013.12.11.15.41.49 for ; Wed, 11 Dec 2013 15:41:49 -0800 (PST) Received-SPF: pass (google.com: best guess record for domain of blah@blahtech.us designates 192.241.174.155 as permitted sender) client-ip=192.241.174.155; Authentication-Results: mx.google.com; spf=pass (google.com: best guess record for domain of blah@blahtech.us designates 192.241.174.155 as permitted sender) smtp.mail=blah@blahtech.us Received: from localhost (localhost [127.0.0.1]) by blahtech.us (Postfix) with ESMTP id 29E78A13FB for ; Wed, 11 Dec 2013 18:41:49 -0500 (EST) X-Virus-Scanned: Debian amavisd-new at blahtech.us Received: from blahtech.us ([127.0.0.1]) by localhost (localhost [127.0.0.1]) (amavisd-new, port 10024) with ESMTP id lvifmUrXjonV for ; Wed, 11 Dec 2013 18:41:48 -0500 (EST) Received: from blah.com (localhost [127.0.0.1]) by blahtech.us (Postfix) with ESMTP id B45E0A13EF for ; Wed, 11 Dec 2013 18:41:48 -0500 (EST) Received: from 50.165.145.244 (SquirrelMail authenticated user blah@blahtech.us) by blah.com with HTTP; Wed, 11 Dec 2013 18:41:48 -0500 Message-ID: <8f7a1823da66577b49c4fccd524b7e95.squirrel@blah.com> Date: Wed, 11 Dec 2013 18:41:48 -0500 Subject: Wed night hockey From: blah@blahtech.us To: blahblah1@gmail.com User-Agent: SquirrelMail/1.4.22 MIME-Version: 1.0 Content-Type: text/plain;charset=iso-8859-1 Content-Transfer-Encoding: 8bit X-Priority: 3 (Normal) Importance: Normal
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31 answers
kamaln7 December 12, 2013
Don't remove localhost, remove blahtech and add a new line above it that says 127.0.0.1 blahtech .

So /etc/hosts will look like this: 
127.0.0.1 blahtech

127.0.0.1 localhost

[...]
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pablo December 12, 2013
"Received: from localhost (localhost [127.0.0.1])"

In all likelihood, there's your problem. A LOT of spammers use localhost in the email header b/c they're relying on a spoofed domain name. So, despite the SPF record, you're sending the receiving mail-servers mixed signals.

Given that your SPF record is using the "hard fail" qualifier, i.e. -all, it's no surprise that Gmail is sending your mail to the Spam folder. It might help to change it to "soft fail," i.e. ~all. See How To use an SPF Record to Prevent Spoofing & Improve E-mail Reliability.

Nevertheless, you're better off with a properly set /etc/hosts file. See Setting the Hostname & Fully Qualified Domain Name (FQDN) on Ubuntu 12.04 or CentOS 6.4 | GitHub.
How To use an SPF Record to Prevent Spoofing & Improve E-mail Reliability
by Pablo Carranza
A carefully tailored SPF record will reduce the likelihood of your domain name getting fraudulently spoofed and keep your messages from getting flagged as spam before they reach your recipients.
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dirk2099 December 12, 2013
Thank you for the help.

I am a little confused on one thing.
I am trying to set the FQDN and right now the /etc/hosts has:
127.0.0.1 localhost blahtech

Should I remove the localhost and have the line say:
127.0.0.1 blahtech

or should i have:
192.241.174.155 blahtech

Thank you
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dirk2099 December 12, 2013
This is how my 
/etc/hosts
file looks like now: 

127.0.0.1 blahtech

127.0.0.1 localhost


If I do 
hostname -f
in the terminal my hostname shows up as blahtech.us which is correct.

But when I send a email the email header still has localhost in it. 


                                                                                                                                                                                                                                                               

Delivered-To: blahblah1@gmail.com

Received: by 10.68.204.97 with SMTP id kx1csp418090pbc;

        Thu, 12 Dec 2013 11:56:56 -0800 (PST)

X-Received: by 10.49.76.66 with SMTP id i2mr16662763qew.35.1386878216527;

        Thu, 12 Dec 2013 11:56:56 -0800 (PST)

Return-Path: 

Received: from blahtech.us (blahtech.us. [192.241.174.155])

        by mx.google.com with ESMTP id e16si19805596qej.91.2013.12.12.11.56.56

        for ;

        Thu, 12 Dec 2013 11:56:56 -0800 (PST)

Received-SPF: pass (google.com: domain of info@blahgranola.com designates 192.241.174.155 as permitted sender) client-ip=192.241.174.155;

Authentication-Results: mx.google.com;

       spf=pass (google.com: domain of info@blahgranola.com designates 192.241.174.155 as permitted sender) smtp.mail=info@blahgranola.com

Received: from localhost (localhost [127.0.0.1])

	by blahtech.us (Postfix) with ESMTP id E3A53A2E4C

	for ; Thu, 12 Dec 2013 14:56:55 -0500 (EST)

X-Virus-Scanned: Debian amavisd-new at blahtech.us

Received: from blahtech.us ([127.0.0.1])

	by localhost (localhost [127.0.0.1]) (amavisd-new, port 10024)

	with ESMTP id M-iVFP5FI675 for ;

	Thu, 12 Dec 2013 14:56:55 -0500 (EST)

Received: from blahblah.com (localhost [127.0.0.1])

	by blahtech.us (Postfix) with ESMTP id A0F7CA2E45

	for ; Thu, 12 Dec 2013 14:56:55 -0500 (EST)

Received: from 50.138.128.223

        (SquirrelMail authenticated user info@blahgranola.com)

        by blahblah.com with HTTP;

        Thu, 12 Dec 2013 14:56:55 -0500

Message-ID: 

Date: Thu, 12 Dec 2013 14:56:55 -0500

Subject: test

From: info@blahgranola.com

To: blahblah1@gmail.com

User-Agent: SquirrelMail/1.4.22

MIME-Version: 1.0

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

Content-Transfer-Encoding: 8bit

X-Priority: 3 (Normal)

Importance: Normal



egre

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kamaln7 December 12, 2013
Did you reboot your droplet?
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dirk2099 December 12, 2013
Nope but I rebooted now and I think its fixed.

I still localhost listed in the header after 
Received: from localhost (blahtech [127.0.0.1])



                                                                                                                                                                                                                                                               

Delivered-To: blahblah1@gmail.com

Received: by 10.68.204.97 with SMTP id kx1csp421854pbc;

        Thu, 12 Dec 2013 12:53:44 -0800 (PST)

X-Received: by 10.224.127.74 with SMTP id f10mr9660112qas.56.1386881624569;

        Thu, 12 Dec 2013 12:53:44 -0800 (PST)

Return-Path: 

Received: from blahtech.us (blahtech.us. [192.241.174.155])

        by mx.google.com with ESMTP id r10si11014534qak.130.2013.12.12.12.53.42

        for ;

        Thu, 12 Dec 2013 12:53:43 -0800 (PST)

Received-SPF: pass (google.com: domain of info@blahgranola.com designates 192.241.174.155 as permitted sender) client-ip=192.241.174.155;

Authentication-Results: mx.google.com;

       spf=pass (google.com: domain of info@blahgranola.com designates 192.241.174.155 as permitted sender) smtp.mail=info@blahgranola.com

Received: from localhost (blahtech [127.0.0.1])

	by blahtech.us (Postfix) with ESMTP id 6AD2AA2E1B

	for ; Thu, 12 Dec 2013 15:53:41 -0500 (EST)

X-Virus-Scanned: Debian amavisd-new at blahtech.us

Received: from blahtech.us ([127.0.0.1])

	by localhost (blahtech.us [127.0.0.1]) (amavisd-new, port 10024)

	with ESMTP id 4Qu-wLkQ3AUt for ;

	Thu, 12 Dec 2013 15:53:41 -0500 (EST)

Received: from blahblah.com (blahtech [127.0.0.1])

	by blahtech.us (Postfix) with ESMTP id E50F2A2CCB

	for ; Thu, 12 Dec 2013 15:53:40 -0500 (EST)

Received: from 50.138.128.223

        (SquirrelMail authenticated user info@blahgranola.com)

        by blahblah.com with HTTP;

        Thu, 12 Dec 2013 15:53:40 -0500

Message-ID: <0ffb94d941b77c6674f3afd011941f6e.squirrel@blahblah.com>

Date: Thu, 12 Dec 2013 15:53:40 -0500

Subject: test66

From: info@blahgranola.com

To: blahblah1@gmail.com

User-Agent: SquirrelMail/1.4.22

MIME-Version: 1.0

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

Content-Transfer-Encoding: 8bit

X-Priority: 3 (Normal)

Importance: Normal



fgregre
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pablo December 12, 2013
"Should I remove the localhost and have the line say:"

No! I provided an example of what your /etc/hosts file should look like @ Setting the Hostname & Fully Qualified Domain Name (FQDN) on Ubuntu 12.04 or CentOS 6.4 | GitHub.
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aguilar1181 December 13, 2013
I don't know if this might be relevant or not. When I created my first droplet, the emails I sent to comcast, gmail, hotmail, and yahoo, were going into spam as well. After researching I found out it was my PTR records that weren't set properly.

So I went into my DO DNS settings and notice my PTR record said server1 and I change it to server1.mydomain.com which is my hostname.

That solved the issue for me.
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pablo December 13, 2013
"After researching I found out it was my PTR records that weren't set properly."

Ya, the How To Create Your First DigitalOcean Droplet Virtual Server article needs a semi-major overhaul.

It appears as though the article was written b/f DigitalOcean rolled out its DNS Manager, but the article was never updated to reflect (i) the importance of PTR records and (ii) the fact that a PTR record is automatically created from the hostname assigned to a droplet in the DigitalOcean Control Panel. Consequently, users that do not format their hostname as a FQDN, in the DO Control Panel, are doomed from the start.
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dirk2099 December 13, 2013
I am seriously confused now. Sorry and I really thank you guys for all the help.

I have the hostname set in my digital ocean control panel to 
blahtech.us
and I have my 
/etc/hosts
file to 
127.0.0.1    blahtech

127.0.0..1    localhost


I also have the 
/etc/hostname
file set to 
blahtech.us


In the DNS records for one of my domain names blahgranola.com I have an "A" record set as 
A   mail    192.241.174.155


Please keep in mind I have several domain names for multiple clients.
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pablo December 13, 2013
If you would only take a look at the article I cited to -- twice before -- you would see that your /etc/hosts file should be formatted like this.
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dirk2099 December 13, 2013
I have been reading your article and I have found it informative but I am a little confused thats all.

I think I have it now. 

127.0.0.1  localhost.localdomain  localhost

127.0.1.1  mail.blahtech.us

127.0.1.1  mail.blahgranola.com

192.241.174.155  mail.blahtech.us 

192.241.174.155  mail.blahgranola.com

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dirk2099 December 13, 2013
Is that a typo in the localhost ip? 127.0.1.1 Shouldn't it be 127.0.0.1?
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pablo December 13, 2013
No, it's not a typo. See 127.0.1.1 ? Ubuntu / Debian and/or /etc/hosts and resolving of the local host/domainname - 127.0.0.1 vs. 127.0.1.1.
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pablo December 13, 2013
"Is that a typo in the localhost ip? 127.0.1.1 Shouldn't it be 127.0.0.1?"

I take back my previous comment. localhost is ALWAYS 127.0.0.1; but, on Debian-based system, such as Ubuntu, you need the second 127.0.1.1 ... line in the /etc/hosts file, as well.
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dirk2099 December 14, 2013
okay so is this correct? I followed what I could from your article and did a little google searching to put this together. Email still goes into gmails spam folder with these settings. I have two domain names here blahtech.us and blahgranola.com

my 
/etc/hosts
file: 

127.0.0.1  localhost.localdomain  localhost

127.0.1.1  btserver.blahtech.us btserver

127.0.1.1  btserver.blahgranola.com btserver

192.241.174.155  btserver.blahtech.us btserver

192.241.174.155  btserver.blahgranola.com btserver


My 
/etc/hostname
file: 
btserver


My digitalocean control panel -> settings -> rename 
btserver


And again thank you for the help.
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pablo December 14, 2013
RE: the Hostname you specify in the DigitalOcean Control Panel

Did you see @Raul Cruz's comment, above? Use a Fully Qualified Domain Name (FQDN), e.g. btserver.blahtech.us.
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dirk2099 December 14, 2013
I set the digitalocean control panel host name to 
btserver.blahtech.us
and email still goes to spam in gmail. Do I need to create any sort of "A" record in my blahtech.us DNS like 
A   btserver  192.241.174.155
?

Or maybe I need to just wait a few hours for everything to resolve?
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pablo December 14, 2013
Both.
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dirk2099 December 14, 2013
Email still goes to spam. I am almost ready to give up. Do you have any other suggestions?
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pablo December 15, 2013
Run each of your domains through the Domain Configuration tool and through easySPF: an Ajax enabled SPF Wizard.
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dirk2099 December 16, 2013
Everything passes except the SOA serial number has a warning and the server returned no glue records. The SPF passes So I am at a loss.

I just noticed hotmail flags email from my server as spam as well. This is not good.

I appreciate all the help.
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pablo December 16, 2013
"I just noticed hotmail flags email from my server as spam as well."

From both domains?
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dirk2099 December 16, 2013
Yes both domains.

I also used this service:
www.mail-tester.com

and my domains have a 9/10 score and the only thing wrong is the message is not signed with DKIM.
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dirk2099 December 17, 2013
Actually Hotmail is excepting emails now. It is just Gmail once again.
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kamaln7 December 18, 2013
Check if your IP address is blacklisted: http://mxtoolbox.com/blacklists.aspx
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dirk2099 December 18, 2013
I think I found the problem. A bot was using a old contact form submission script that I had forgotten about years ago on my server to spam the hell out of my gmail account. I never had any bot checks on that script so the bot was able to send over a 100 emails a day to my gmail account. Gmail must of blacked flagged the servers IP from this.

I have removed the script and the spam has stopped.

I am hoping maybe within a few days or so this might clear up the spam flag and if not I may have to change the servers IP and see if that helps.

I appreciate all the help from everyone here. If anything I was able to fix a bunch of other issues with my email server from the help of the people here.

Thank you
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pablo December 18, 2013
You may also want to check out Postfix/DKIM | Ubuntu Docs.
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aheihachi February 13, 2014
50% of digital ocean's AMS datacenter's IP's are blacklisted. That's why your email are going in to a spam folder in gmail.
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  • metaprinter December 7, 2014

    Assuming this is true…

    1. is this something i can control/avoid with proper mail server/DNS/FQDN setup or is it a roll of the dice depending on the IP of my droplet?
    2. Is there a common alternative you could share?
    Reply Report
franklynd May 16, 2014
is that true ?
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luissh84 May 19, 2014
I have the same problem, in my mails appears Received: from mydomain.com (mydomain.com[127.0.0.1]), anyone knows how can I resolve it?
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lorenz September 11, 2014
[deleted]
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