E-mail always send to spam folder

Question

I have an VPS that has a pre-installed DirectAdmin and exim mailservice. But i've got a complainment from my client.

When he tries and send an e-mail from his account to someone it gets flagged as spam.

Here is the full e-mail message with all the headers and stuff. i hope someone can help me

    Authentication-Results: hotmail.com; spf=pass (sender IP is 141.138.205.229) smtp.mailfrom=info@dutchtwinz.com; dkim=none header.d=dutchtwinz.com; x-hmca=pass header.id=info@dutchtwinz.com
X-SID-PRA: info@dutchtwinz.com
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0wO0Q9MjtHRD0yO1NDTD00
X-Message-Info: /3z5fcrqMMU004j2/ma9gxjYaCTHh1SYDRkBozv0u0RQKYi/p3JnhYDq+fCL9gd4ZoOdwyC8ZUOO2jFRJx3dhfsqqC1/dh3dpEFRPyEuAPqxYkG1kNuhS/+RxWTrmmRKMIiVYIDsa9HA3Jo5r2TlC2nKN74iRkxxZa345HzmY6vbD4SELXiO9OGS366OsWVIWlbDpo9jcpthAtNsCaKurN4SaoraB0Mk
Received: from 117.lemoninternetbureau.nl ([141.138.205.229]) by SNT004-    MC3F21.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.22712);
 Sun, 21 Sep 2014 06:48:32 -0700
Received: from localhost ([127.0.0.1] helo=webmail.dutchtwinz.com)
by 117.lemoninternetbureau.nl with esmtpa (Exim 4.82)
(envelope-from <info@dutchtwinz.com>)
id 1XVhV9-0004Nt-28
for lemoninternet@outlook.com; Sun, 21 Sep 2014 15:48:31 +0200
MIME-Version: 1.0
Content-Type: multipart/alternative;
boundary="=_12ba68aba8975b804caf848a8d980657"
Date: Sun, 21 Sep 2014 15:48:31 +0200
From: Dutchtwinz <info@dutchtwinz.com>
To: lemoninternet@outlook.com
Subject: Test
Organization: DTE Booking Agency
Reply-To: info@dutchtwinz.com
Mail-Reply-To: info@dutchtwinz.com
Return-Receipt-To: Dutchtwinz <info@dutchtwinz.com>
Disposition-Notification-To: Dutchtwinz <info@dutchtwinz.com>
Message-ID: <d37039273be133d3b75de0c752fc884b@dutchtwinz.com>
X-Sender: info@dutchtwinz.com
User-Agent: Roundcube Webmail/1.0.0
Return-Path: info@dutchtwinz.com
X-OriginalArrivalTime: 21 Sep 2014 13:48:32.0602 (UTC) FILETIME=[BB9C13A0:01CFD5A2]

--=_12ba68aba8975b804caf848a8d980657
Content-Transfer-Encoding: 7bit
Content-Type: text/plain




    Test
-- 
Public Relations Dutch Twinz Entertainment
Amsterdam, The Netherlands Tel:
0031 645241556 Website:
http://www.dutchtwinz.com

--=_12ba68aba8975b804caf848a8d980657
Content-Transfer-Encoding: quoted-printable
Content-Type: text/html; charset=UTF-8

<!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN">
<html><body style=3D'font-size: 10pt; font-family: Verdana,Geneva,sans-serif='>
<pre>Test
--=20
Public Relations Dutch Twinz Entertainment
Amsterdam, The Netherlands                                           Tel:
0031 645241556                                                     Website:
http://www.dutchtwinz.com</pre> 
</body></html>

--=_12ba68aba8975b804caf848a8d980657--

I already have added spf records + reverse DNS addresses for my server. Also i added ipv6 records for the domains, (server domain + client domain) — Rickerd, Sep 21 '14 at 14:11
Hotmail is *always* a pain. They don't stick to the SMTP-standards. Boycott it. — sebix, Sep 21 '14 at 14:32

score 1 · Answer 1 · answered Sep 21 '14 at 14:24

Lets looks at your mail setup for the outside .

first your MX record is a bit odd (This doesn't have anything to do with the spam folder, but you should probably fix it. to only include 1 record per IP,

[~] host -tmx  dutchtwinz.com
dutchtwinz.com mail is handled by 10 pop.dutchtwinz.com.
dutchtwinz.com mail is handled by 10 smtp.dutchtwinz.com.
dutchtwinz.com mail is handled by 10 mail.dutchtwinz.com.
dutchtwinz.com mail is handled by 10 imap.dutchtwinz.com.
dutchtwinz.com mail is handled by 10 pop3.dutchtwinz.com.

they all point your single IP of 141.138.205.229, so just remove all save for mail and it would look more normal.

your IP has a PTR, and it resolves back to your IP, so that is good.

[~] host 141.138.205.229
229.205.138.141.in-addr.arpa domain name pointer 117.lemoninternetbureau.nl.
[~] host 117.lemoninternetbureau.nl
117.lemoninternetbureau.nl has address 141.138.205.229
117.lemoninternetbureau.nl has IPv6 address 2a02:348:84:cde5::1

and your mail server HELO's as your name

[~] telnet  117.lemoninternetbureau.nl 25
Trying 141.138.205.229...
Won't send login name and/or authentication information.
Connected to 117.lemoninternetbureau.nl.
Escape character is '^]'.
220 117.lemoninternetbureau.nl ESMTP Exim 4.82 Sun, 21 Sep 2014 16:11:21 +0200

so that is good. A == PTR == HELO.

[~] host -t spf dutchtwinz.com
dutchtwinz.com has no SPF record
[~] host -t txt dutchtwinz.com
dutchtwinz.com descriptive text "google-site-verification=TA_T5RfvDX1R2fsaq29sQsAg1e0LFtFi8OWduzmZNrw"
dutchtwinz.com descriptive text "v=spf1 a mx ip4:141.138.205.229 ip6:2a02:348:84:cde5::1 ~all"

your domain has an SPF record that covers your host. I don't see a DKIM signature in the headers. you Might try enabling DKIM, as that can help with delivery to hotmail.

Also in looking it looks like you don't send a lot of email, and there isn't a lot in terms of reputation of your IP/domain. So that is probably working against you as well.

You should tell your clients to mark the messages as not spam in hotmail, which should help with future messages not going to the spam folder.

Thanks for the lookups! I have managed already alot i think but is it really necessary to add a DKIM? It looks a little to much if you ask me. And if i tell my clients that i can't do much about it they will go mad, which i can understand. — Rickerd, Sep 21 '14 at 14:38
Every little bit helps. So adding DKIM can help especially with delivery to yahoo. But it can be annoying to setup and get the selectors right especially if you are hosting multiple domains and want to sign each with differnet keys. There are many reasons things get thrown in the spam folder. From content to server rep to combinations of both. My normal response is your hotmail account is worth how much you pay for it ;) — Doon, Sep 21 '14 at 14:52

E-mail always send to spam folder

1 Answers1