1 Topic by kemical

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Topic: Why is Hotmail still tagging my email as spam?

==== Required information ====
- iRedMail version (check /etc/iredmail-release): iRedmail 0.9.2
- Linux/BSD distribution name and version: Debian 7
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): MySQL
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====

Hi.
I'm having a problem with my emails which are sent to hotmail accounts. According to mail-tester.com I have 10/10 score so I don't know why Hotmail tags my emails as spam. Mail-tester only warns me due to the rDNS (PTR) points to different domain (vps.anotherdomain.pl) but I've solved this and now reverse lookup tools show the correct FQDN (Don't know why mail-tester still warns about this).

The headers of my emails are

Received: from mymachine.mydomain.com ([myIP]) by COL004-MC3F30.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.23008);
     Wed, 8 Jul 2015 00:52:06 -0700
Received: from mymachine.mydomain.com (localhost.localdomain [127.0.0.1])
    by mymachine.mydomain.com (Postfix) with ESMTP id 578DE82BF5
    for <someone@hotmail.com>; Wed,  8 Jul 2015 03:52:05 -0400 (EDT)
Authentication-Results: mymachine.mydomain.com (amavisd-new);
    dkim=pass (1024-bit key) reason="pass (just generated, assumed good)"
    header.d=mydomain.com

Btw, this line 

Received: from mymachine.mydomain.com (localhost.localdomain [127.0.0.1])

shouldn't be like?

Received: from mymachine.mydomain.com (mymachine.mydomain.com [myIP])

Thanks in advance!

----

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2 Reply by 7t3chguy

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Re: Why is Hotmail still tagging my email as spam?

The PTR should point to the FQDN in the MX Record, so if your MX Record says mailserv1.yourdomain.com then your PTR has to point to that for some mail checks to be happy, internal headers have to match this too. And just because a few testers give your mail the all-clear doesn't mean that someone as strict as Hotmail will let it through, your best bet is to contact them and ask them what's preventing mail delivery.

And that line is like that because your services are all on the same machine, and it uses the internal (lo) interface

7t3chguy's Website

3 Reply by kemical

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Re: Why is Hotmail still tagging my email as spam?

7t3chguy wrote:

The PTR should point to the FQDN in the MX Record, so if your MX Record says mailserv1.yourdomain.com then your PTR has to point to that for some mail checks to be happy, internal headers have to match this too. And just because a few testers give your mail the all-clear doesn't mean that someone as strict as Hotmail will let it through, your best bet is to contact them and ask them what's preventing mail delivery.

And that line is like that because your services are all on the same machine, and it uses the internal (lo) interface

Thank you so much for your fast answer. I changed the PTR to the MX Record. Lastly, how can I contact with Hotmail to prevent this issue?

4 Reply by ZhangHuangbin

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Re: Why is Hotmail still tagging my email as spam?

kemical wrote:

Received: from mymachine.mydomain.com (localhost.localdomain [127.0.0.1])

I'm not sure whether 'localhost.localdomain' matters for Hotmail. but you can change it by updating '$myhostname' and '$localhost_name' in /etc/amavis/conf.d/50-user.

Also, please make sure command 'hostname -f' always return the correct FQDN (list FQDN as first domain name of 127.0.0.1 in /etc/hosts and /var/spool/postfix/etc/hosts).

5 Reply by kemical

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Re: Why is Hotmail still tagging my email as spam?

ZhangHuangbin wrote:
kemical wrote:

Received: from mymachine.mydomain.com (localhost.localdomain [127.0.0.1])

I'm not sure whether 'localhost.localdomain' matters for Hotmail. but you can change it by updating '$myhostname' and '$localhost_name' in /etc/amavis/conf.d/50-user.

Also, please make sure command 'hostname -f' always return the correct FQDN (list FQDN as first domain name of 127.0.0.1 in /etc/hosts and /var/spool/postfix/etc/hosts).

It seems that the problem is on my /etc/hosts. I don't know why when I put in my /etc/hosts

127.0.0.1 myvps.mydomain.com localhost.localdomain localhost

And then when I reboot the server, automatically becomes to

127.0.0.1 localhost.localdomain localhost myvps.mydomain.com

6 Reply by ZhangHuangbin

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Re: Why is Hotmail still tagging my email as spam?

Is it a Debian system "issue"?

7 Reply by kemical

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Re: Why is Hotmail still tagging my email as spam?

ZhangHuangbin wrote:

Is it a Debian system "issue"?

Yes, I'm using Debian

8 Reply by 7t3chguy

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Re: Why is Hotmail still tagging my email as spam?

kemical wrote:
ZhangHuangbin wrote:

Is it a Debian system "issue"?

Yes, I'm using Debian

I think it's a cloud-init thing rather than Debian

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9 Reply by kemical

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Re: Why is Hotmail still tagging my email as spam?

7t3chguy wrote:
kemical wrote:
ZhangHuangbin wrote:

Is it a Debian system "issue"?

Yes, I'm using Debian

I think it's a cloud-init thing rather than Debian

You mean that it's something related to my VPS provider right?

10 Reply by ZhangHuangbin

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Re: Why is Hotmail still tagging my email as spam?

kemical wrote:

You mean that it's something related to my VPS provider right?

I guess so. Did you try to contact your VPS provider to figure it out?