1 Topic by jackmullen

  • jackmullen
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Topic: Outlook denying all emails

======== Required information ====
- iRedMail version (check /etc/iredmail-release): 0.9.2
- Linux/BSD distribution name and version: Ubuntu 14.04 LTS
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): MySQL
- Web server (Apache or Nginx): Apache
- Manage mail accounts with iRedAdmin-Pro? No
- Related log if you're reporting an issue:
====

Hi,

We're currently having an issue with our iRedMail server. Any emails sent to an outlook or hotmail account are not even turning up in the mailbox. I've sent a message to Microsoft's Deliverability Support who told me that my email was being classed as spam by their Smartscreen filter, and that my email deliverability issue would not be mitigated.

We're only sending a few emails and I think the amount of spam being sent from our address is non-existent.

The only time emails are being recieved is when the user is replying to an email sent by an outlook or hotmail user. I managed to use this to view the header that was being sent:

x-store-info:SmXCjkY1Un5L3qlTmewTw2528Vzv4BD3bvtVwVJQXw8P3qPhGd5O6SYrcbjW0zpNf3N00J9aem/Yg9nVJ3NUTCm3J4kVFZNQ05AtSDLC7JJYaSTFejPE8hRWI+ReWGDEE2vzRgzVefQ=
Authentication-Results: hotmail.com; spf=pass (sender IP is 159.203.83.32) smtp.mailfrom=jack.m@nervemedia.org.uk; dkim=pass header.d=nervemedia.org.uk; x-hmca=pass header.id=jack.m@nervemedia.org.uk
X-SID-PRA: jack.m@nervemedia.org.uk
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MTtsPTE7YT0wO0Q9MDtHRD0wO1NDTD03
X-Message-Info: wrj6pbeLyoMLNMdMF8TB4w5HdNWsl4z/N2qpkYAMPTL6fAo6CYzdjlNfyn9P/yRvP+WagcRRGxrp1xPA85WO8UR8k4giYVjJzrvXaZmTlj/SdklvHF76p+ISIqh7WPhVNh6Gt9HbMGbGV2YMpK9u3htVcaw15Fjay0I1a7H+dd0bpElYrsCh/55P6bbNyvcdU7QBP4pOvRCGrtGHwDM0r8C5o9in6AWJfzc1srcymso=
Received: from email.nervemedia.org.uk ([159.203.83.32]) by COL004-MC2F13.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.23143);
     Sun, 11 Oct 2015 11:20:36 -0700
Received: from email.nervemedia.org.uk (unknown [127.0.0.1])
    by email.nervemedia.org.uk (Postfix) with ESMTP id C19681421FF
    for <jackmullen1994@outlook.com>; Sun, 11 Oct 2015 14:20:35 -0400 (EDT)
Authentication-Results: email.nervemedia.org.uk (amavisd-new);
    dkim=pass (2048-bit key) reason="pass (just generated, assumed good)"
    header.d=nervemedia.org.uk
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=
    nervemedia.org.uk; h=user-agent:message-id:references
    :in-reply-to:subject:subject:to:from:from:date:date:content-type
    :content-type:mime-version; s=dkim; t=1444587635; x=1445451636;
     bh=YYqOf2gnTP1CMPafIIAnYTOC6BtWs+Xecqff7IzoQ6E=; b=T1lJQgtgAaiC
    1cet2QMMSGwWLS+qSQfn7z58blGc/CZNvWbXiXfkSbQoliti54S7vdq3bSxgsWlN
    sZBw3W49eokP6nmfuEb3S7uJJXw4Bv9/uavY3wdQB+17+KRAmCR7GS0IWkitb2k4
    PpyTo3hC9PIpjwUCay/N+WFRMUpfkUnKiHOmKFdf1UIpmKgCZWDARgnrQnmacoPS
    dNVS+48csMGSDlYRSEMAZ62n1DpQm/+2cGAKjEN/SpaEqgoO5KtwLbh5uxaLuDaX
    rX3R4f5kSrLro/2u+3WLR2ordEm4A0e+k89neLqLopNPNHZebcuIHTZTlLSsJPeX
    x9BWzOx9Jg==
X-Virus-Scanned: Debian amavisd-new at email.nervemedia.org.uk
Received: from email.nervemedia.org.uk ([127.0.0.1])
    by email.nervemedia.org.uk (email.nervemedia.org.uk [127.0.0.1]) (amavisd-new, port 10024)
    with ESMTP id OoQ3-qtV9AiT for <jackmullen1994@outlook.com>;
    Sun, 11 Oct 2015 14:20:35 -0400 (EDT)
MIME-Version: 1.0
Content-Type: multipart/alternative;
 boundary="=_cf849a907d59eba38073bda0cad50da0"
Date: Sun, 11 Oct 2015 19:20:34 +0100
From: jack.m@nervemedia.org.uk
To: J Mullen <jackmullen1994@outlook.com>
Subject: Re: Hello
In-Reply-To: <SNT150-W19524BF45A363C36219BD4C9340@phx.gbl>
References: <SNT150-W19524BF45A363C36219BD4C9340@phx.gbl>
Message-ID: <2c420564f7ca87eab0e08216e0dbd438@nervemedia.org.uk>
X-Sender: jack.m@nervemedia.org.uk
User-Agent: Roundcube Webmail
Return-Path: jack.m@nervemedia.org.uk
X-OriginalArrivalTime: 11 Oct 2015 18:20:36.0790 (UTC) FILETIME=[869F3D60:01D10451]

mxtoolbox reports a DMARC issue, but apart from that it seems fine. All other emails to other providers (gmail, yahoo) is working fine.

Any advice would be greatly appreciated! I am loving iRedMail in general, I've just had a bit of a tricky day trying to get my head around Microsoft's bizarre filter.

----

Spider Email Archiver: On-Premises, lightweight email archiving software developed by iRedMail team. Supports Amazon S3 compatible storage and custom branding.

2 Reply by ZhangHuangbin

  • ZhangHuangbin
  • ZhangHuangbin
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Re: Outlook denying all emails

jackmullen wrote:

Any emails sent to an outlook or hotmail account are not even turning up in the mailbox.

What's the error message in Postfix log file (/var/log/mail.log)?

I see you have SPF/DKIM DNS records.

jackmullen wrote:

mxtoolbox reports a DMARC issue

What issue? Show us the details so that others can help troubleshoot.

3 Reply by jackmullen

  • jackmullen
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Re: Outlook denying all emails

This is the log section for me sending out an email to an outlook account (and it not appearing in the inbox).

Oct 12 13:00:12 email postfix/smtpd[14704]: connect from email.nervemedia.org.uk[127.0.0.1]
Oct 12 13:00:12 email postfix/smtpd[14704]: 880FA143A0A: client=email.nervemedia.org.uk[127.0.0.1], sasl_method=LOGIN, sasl_username=jack.m@nervemedia.$
Oct 12 13:00:13 email postfix/cleanup[14710]: 880FA143A0A: message-id=<b97c5184d72394ca7ffd73206f355550@nervemedia.org.uk>
Oct 12 13:00:13 email postfix/qmgr[1893]: 880FA143A0A: from=<jack.m@nervemedia.org.uk>, size=1069, nrcpt=1 (queue active)
Oct 12 13:00:13 email roundcube: <rnurfcps> User jack.m@nervemedia.org.uk [109.157.110.123]; Message for jackmullen1994@outlook.com; 250: 2.0.0 Ok: que$
Oct 12 13:00:13 email postfix/smtpd[14704]: disconnect from email.nervemedia.org.uk[127.0.0.1]
Oct 12 13:00:13 email postfix/smtpd[14722]: warning: hostname email.nervemedia.org.uk does not resolve to address 127.0.0.1
Oct 12 13:00:13 email postfix/smtpd[14722]: connect from unknown[127.0.0.1]
Oct 12 13:00:13 email postfix/smtpd[14722]: F3394143A0E: client=unknown[127.0.0.1]
Oct 12 13:00:13 email postfix/cleanup[14710]: F3394143A0E: message-id=<b97c5184d72394ca7ffd73206f355550@nervemedia.org.uk>
Oct 12 13:00:14 email postfix/qmgr[1893]: F3394143A0E: from=<jack.m@nervemedia.org.uk>, size=2386, nrcpt=1 (queue active)
Oct 12 13:00:14 email postfix/smtpd[14722]: disconnect from unknown[127.0.0.1]
Oct 12 13:00:14 email amavis[11741]: (11741-09) Passed CLEAN {RelayedInternal}, MYNETS/MYUSERS LOCAL [127.0.0.1]:46526 <jack.m@nervemedia.org.uk> -> <j$
Oct 12 13:00:14 email postfix/smtp[14717]: 880FA143A0A: to=<jackmullen1994@outlook.com>, relay=127.0.0.1[127.0.0.1]:10024, delay=1.5, delays=1.1/0.02/0$
Oct 12 13:00:14 email postfix/qmgr[1893]: 880FA143A0A: removed
Oct 12 13:00:15 email postfix/smtp[14723]: F3394143A0E: to=<jackmullen1994@outlook.com>, relay=mx1.hotmail.com[65.55.37.72]:25, delay=2, delays=0.01/0.$
Oct 12 13:00:15 email postfix/qmgr[1893]: F3394143A0E: removed

The dmarc issue reported from mxtoolbox just says:

dmarc    nervemedia.org.uk    Missing or Invalid Record

There are also two more issues that it reports

dns    nervemedia.org.uk    SOA Serial Number Format is Invalid 
dns    nervemedia.org.uk    SOA Expire Value out of recommended range

If it makes a difference, this server is currently on a DigitalOcean droplet.

Many thanks!

4 Reply by ZhangHuangbin

  • ZhangHuangbin
  • ZhangHuangbin
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Re: Outlook denying all emails

No error in your log file while sending to outlook.com. Is your server IP address listed in some DNSBL service? Check it here:
http://mxtoolbox.com/blacklists.aspx

5 Reply by jackmullen

  • jackmullen
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Re: Outlook denying all emails

ZhangHuangbin wrote:

No error in your log file while sending to outlook.com. Is your server IP address listed in some DNSBL service? Check it here:
http://mxtoolbox.com/blacklists.aspx

It's not blacklisted anywhere as far as I can tell. I've used several blacklist checkers including the one you linked too and they all come back as passing every single blacklist service.

6 Reply by ZhangHuangbin

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Re: Outlook denying all emails

No idea yet. Usually outlook.com blocks client due to blacklisted in some DNSBL services, but you claim your ip is clean. I'm afraid you have to contact Outlook.com support to know how to avoid this.

7 Reply by mir (edited by mir 2015-10-14 02:53:34)

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Re: Outlook denying all emails

I think this is your problem:
email.nervemedia.org.uk[127.0.0.1]

Your mail server claims to have ip 127.0.0.1 which is clearly wrong. Your mail server needs to advertise its public IP which happens to be: 159.203.83.32

8 Reply by jackmullen

  • jackmullen
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Re: Outlook denying all emails

ZhangHuangbin wrote:

No idea yet. Usually outlook.com blocks client due to blacklisted in some DNSBL services, but you claim your ip is clean. I'm afraid you have to contact Outlook.com support to know how to avoid this.

I have emailed Microsoft and can get little information from them apart from the fact that SmartScreen filter has blocked the emails and that they won't mitigate the deliverability issue.

mir wrote:

I think this is your problem:
email.nervemedia.org.uk[127.0.0.1]

Your mail server claims to have ip 127.0.0.1 which is clearly wrong. Your mail server needs to advertise its public IP which happens to be: 159.203.83.32

Is there a way to change this? I did notice this earlier, along with the fact that the header contains:

Received: from email.nervemedia.org.uk (unknown [127.0.0.1])

9 Reply by mir

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Re: Outlook denying all emails

What do you have in your /etc/hosts file?

Try this:
159.203.83.32 email.nervemedia.org.uk

And remove email.nervemedia.org.uk from the line containing 127.0.0.1

10 Reply by jackmullen

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Re: Outlook denying all emails

mir wrote:

What do you have in your /etc/hosts file?

Try this:
159.203.83.32 email.nervemedia.org.uk

And remove email.nervemedia.org.uk from the line containing 127.0.0.1

My hosts file now looks like this:

127.0.1.1 email.nervemedia.org.uk email.nervemedia.org.uk
127.0.0.1 localhost
159.203.83.32 email.nervemedia.org.uk

# The following lines are desirable for IPv6 capable hosts
::1 ip6-localhost ip6-loopback
fe00::0 ip6-localnet
ff00::0 ip6-mcastprefix
ff02::1 ip6-allnodes
ff02::2 ip6-allrouters
ff02::3 ip6-allhosts

The "unknown" from the header has gone, but there are still local IP's in there:

x-store-info:SmXCjkY1Un5L3qlTmewTw2528Vzv4BD3QOVyEFvSkelJpfdjKmne+O82trsI93+RYOo0e+qPUF0CnF2xp7bcJHZZBe0NYLldVgmUcLPnvN6xjXtZfXglQmxzsy7yJlHn9j8A0NADsAo=
Authentication-Results: hotmail.com; spf=pass (sender IP is 159.203.83.32) smtp.mailfrom=jack.m@nervemedia.org.uk; dkim=pass header.d=nervemedia.org.uk; x-hmca=pass header.id=jack.m@nervemedia.org.uk
X-SID-PRA: jack.m@nervemedia.org.uk
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MTtsPTE7YT0wO0Q9MDtHRD0wO1NDTD03
X-Message-Info: wrj6pbeLyoMLNMdMF8TB49sclH73QLaWxdzXLneIZMr5Gol0M8Hk6ppzKwbPFihZWD5fhlXSJxKenMFwHUHujbRw0nm/yqtWQELbMxcqZylJUoM3h8B1mwEyuYF6oD8GXK549TWjyV4v2c2KHJeAXPOZUAur68ZWGIxia8AdwjOIKdJl9hqSkiw68EojgLTBhHmgpXbD3VMzNUuSSfmeQfDnjSWwC2m/MnITpK03q4Y=
Received: from email.nervemedia.org.uk ([159.203.83.32]) by SNT004-MC4F17.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.23143);
     Tue, 13 Oct 2015 14:32:30 -0700
Received: from email.nervemedia.org.uk (localhost [127.0.0.1])
    by email.nervemedia.org.uk (Postfix) with ESMTP id BAEBB1432CC
    for <jackmullen1994@outlook.com>; Tue, 13 Oct 2015 17:32:29 -0400 (EDT)
Authentication-Results: email.nervemedia.org.uk (amavisd-new);
    dkim=pass (2048-bit key) reason="pass (just generated, assumed good)"
    header.d=nervemedia.org.uk
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/simple; d=
    nervemedia.org.uk; h=user-agent:message-id:references
    :in-reply-to:subject:subject:to:from:from:date:date:content-type
    :content-type:mime-version; s=dkim; t=1444771949; x=1445635950;
     bh=LsRbqEX9V2Q43+boYH7Za4PcpksV9IrrxZk95vmSWOI=; b=c96pf62OIFVl
    zuTs41nsbG2eNsWBPrK/fc+3qE1gBMHxUOcvwuJ/enIgxynhGSRVjp0jGwL5tpRf
    yEf9G4mITjnf4HxAgABJXWbKv8iSpQZADfQNq+nZAgMPp7NukTMryeBmnle9zuii
    cEZKSifTd+0zMolX/abmaEP328NfKsemaypsKA5y5gENTwkgRWUD7caU3DLbV69r
    Ijfb5YOxEAyT9F5jFWgJvIE0ey2dL0r/J/A7C6F9WkGbe05A3oiTBtTy7Xlx9jfd
    tWvjTsOzzixyCn4d+x6OeQIzEVwwtPvZb4nm/fve1J6aD4vByBtzBCL4TY8EBFYO
    xRJfP2IoDQ==
X-Virus-Scanned: Debian amavisd-new at email.nervemedia.org.uk
Received: from email.nervemedia.org.uk ([127.0.0.1])
    by email.nervemedia.org.uk (email.nervemedia.org.uk [127.0.0.1]) (amavisd-new, port 10024)
    with ESMTP id w7P5wr9nK3Wq for <jackmullen1994@outlook.com>;
    Tue, 13 Oct 2015 17:32:29 -0400 (EDT)
MIME-Version: 1.0
Content-Type: multipart/alternative;
 boundary="=_0b16cc40b80f938fd14803acb3ec87aa"
Date: Tue, 13 Oct 2015 22:32:27 +0100
From: jack.m@nervemedia.org.uk
To: J Mullen <jackmullen1994@outlook.com>
Subject: Re: Hello
In-Reply-To: <SNT150-W19524BF45A363C36219BD4C9340@phx.gbl>
References: <SNT150-W19524BF45A363C36219BD4C9340@phx.gbl>
Message-ID: <29b68e813c6c531690dd03646e0512ee@nervemedia.org.uk>
X-Sender: jack.m@nervemedia.org.uk
User-Agent: Roundcube Webmail
Return-Path: jack.m@nervemedia.org.uk
X-OriginalArrivalTime: 13 Oct 2015 21:32:30.0478 (UTC) FILETIME=[AA241AE0:01D105FE]

11 Reply by ZhangHuangbin

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Re: Outlook denying all emails

This header usually doesn't impact, it's quite normal.

12 Reply by jackmullen (edited by jackmullen 2015-10-24 03:06:50)

  • jackmullen
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Re: Outlook denying all emails

Apologies for not posting in here sooner, but I just want to add this quick message to anyone who discovers this post and is interested in what happened. Many thanks to both of you who helped with this btw, I'm loving iRedMail and the support and information on this website is really useful!

So I got in contact with the Microsoft Deliverability Team again, this time requesting that my issue was escalated above their first line support. After 3 days I got a reply from a technician who said that the SmartScreen filter was denying all my mail and could provide no further information, so I gave up.

I decided to move to Plan B, which was to image the server and create a new server (I'm using DigitalOcean) so that I could be assigned a new IP address. After transferring the image to this new server everything worked fine, and outlook and hotmail email goes to inbox.

I'm assuming there may have been some history associated with that IP, as I can't really understand any other way that my new server would be accepted while the old one would be rejected. It would be interesting to know if anyone else has had a similar issue in the past and if they've got any information to share on this, but I'm just grateful that everything is working fine for now!

Thanks again smile

13 Reply by ZhangHuangbin

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Re: Outlook denying all emails

Thanks for sharing.

BTW, did you contact MS again and ask them to unblock this (old) IP?

14 Reply by jackmullen (edited by jackmullen 2015-10-25 01:03:09)

  • jackmullen
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Re: Outlook denying all emails

ZhangHuangbin wrote:

Thanks for sharing.

BTW, did you contact MS again and ask them to unblock this (old) IP?

No I didn't. I was given a categorical "no" when I was using that IP, so I'm not convinced I could do much to change their mind even if I demonstrated emails now work fine from this new IP.