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Mail rejected by Windows Live Hotmail for policy reasons

Posted on 2011-10-18
Medium Priority
Last Modified: 2012-05-12
I am not able to send email to any hotmail email address from the itmstratford.co.nz domain. All other sending of email from the site is OK. The ITM Stratford users receive the following message immediately from hotmail when they attempt to send a message to any hotmail address.

Delivery has failed to these recipients or distribution lists:
An error occurred while trying to deliver this message to the recipient's e-mail address. Microsoft Exchange will not try to redeliver this message for you. Please try resending this message, or provide the following diagnostic text to your system administrator.
 The following organization rejected your message: col0-mc3-f11.Col0.hotmail.com.
Sent by Microsoft Exchange Server 2007

 Diagnostic information for administrators:
 Generating server: STITM01.itmstratford.local
col0-mc3-f11.Col0.hotmail.com #550 OU-002 (COL0-MC3-F11) Unfortunately, messages from weren't sent. Please contact your Internet service provider since part of their network is on our block list. You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors. ##
 Original message headers:
 Received: from STITM01.itmstratford.local ([fe80::104a:43c3:1e8c:acd2]) by
 STITM01.itmstratford.local ([fe80::104a:43c3:1e8c:acd2%10]) with mapi; Tue,
 18 Oct 2011 08:25:35 +1300
From: xxxx<xxx@itmstratford.co.nz>
To: "xyz@hotmail.com" <xyz@hotmail.com>
Date: Tue, 18 Oct 2011 08:25:34 +1300
Subject: TEST
Thread-Topic: TEST
Thread-Index: AcyNAorAgXq6lpSATaCkS0PyYaVlKg==
Message-ID: <9164113D3C79CB4E8170A8129190B5AC0139D3F454DA@STITM01.itmstratford.local>
Accept-Language: en-US
Content-Language: en-US
acceptlanguage: en-US
Content-Type: multipart/alternative;
MIME-Version: 1.0

I suspect Hotmail / Windows Live have blacklisted itmstratford.co.nz somehow, however the domain is not on any RBL listing that I can find and it appears to come up clean.
I have checked with the companies ISP as well, Clear.net.nz and all is OK. Again the mail server IP has been checked and the ISP has also confirmed that it is not black listed. The ISP is able to send email to hotmail.com with no problem so I understand the issue is not with the ISP and not on the local mail server?
An explaination given based on the error reads something like this:
The Mail could be rejected by Windows Live Hotmail for policy reasons. Reasons for rejection may be related to content with spam-like characteristics or IP/domain reputation. If you are not an email/network admin please contact your Email/Internet Service Provider for help.

The ISP thing has just been done and I am wondering if there is a "Private" database at the Hotmail end that needs to be updated to resolve the issue?

I would be glad if someone could point me in the right direction because it appears that we are not able to speak to Hotmail directly. How do we engage Hotmail to check this as I have used their forum and have had no response as yet?
Is there something else I can do please? Oh yes the SBS 2008 system is on a private 192.168.0.xxx network.
Question by:Compuit1
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LVL 26

Assisted Solution

by:Brian B
Brian B earned 1000 total points
ID: 36986037
Whether their ISP thinks there is a problem or not, I would have them test and see what is going on. As the message says, there is nothing you can do as an individual since it looks like the IP range is blocked for some reason. Perhaps another company on the same IP range had a spam problem.

Worst case, see if their ISP has a smart host you can bounce their mail through. Make sure you change the rDNS is they have one, but at least then if there are still problem it really is the ISPs issue.
LVL 26

Expert Comment

by:Brian B
ID: 36986501
I would still push the ISP for help, but here is the things MS says you should look at:
http://mail.live.com/mail/troubleshooting.aspx. There is mention of a few thing you should look at, like sender authentication, rDNS, etc.
LVL 78

Expert Comment

by:Rob Williams
ID: 36987848
Two common reasons for being blocked by Hotmail/Live are the ISP has been blacklisted, or Hotmail believes (true or not) you are sending from a dynamic IP. You may also find you are blocked by aol.com and att.com, those three seem to use the same policies.
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Author Comment

ID: 36988624
Thank you for the responses. As a plan of action I will follow-up the rDNS because I see the following on the help page that may be relevant

1.) Are you advertising yourself as a non-routable IP?
We may not accept email from senders who fail a reverse-DNS lookup. In some cases legitimate senders advertise themselves incorrectly as a non-internet routable IP when attempting to open a connection to Hotmail. IP addresses that are reserved for private (non-routable) networking are,, and (or -, -, -

The mail server is on a private network. How do I test and resolve the Reverse DNS-Look-up?

2.) I will check in again with the ISP. (Smart host approach?)

3.) I see there is an option to further pursue contact with Hotmail

Thank you I will be in touch.

Author Comment

ID: 36988655
Oh yes the site does get a static IP ( from the ISP but it comes from the ISPs dynamic IP pool. I see the router is set to dynamically assigned WAN IP.
LVL 78

Expert Comment

by:Rob Williams
ID: 36988789
If Hotmail considres the IP ans part of a Dynamic adrress pool thy may block it. It sounds like you may have what is refered to as a "sticky IP" by some ISP's. Basically a DHCP reservation. If so they may not be willing to set up a reverse DNS. A smarthost in that case is by far the best option.

Author Comment

ID: 36988889
Hello Rob - Thank you it sounds like the Smart Host option is the most trouble free. I like that. Investigating right now.
LVL 78

Accepted Solution

Rob Williams earned 1000 total points
ID: 36989344
If you have SBS 2008 you can add a smart host in the SBS control panel quite easily, under network / connecivity, there is a wizard to do it for you. You just need your ISP's smtp server FQDN

Author Comment

ID: 36990600
Hi TBone and Rob,
Right I gave up on the Windows Live  / Hotmail forum and help and took the advice given to use the ISP as a smart host. The configuration was simple in exchange management console --> under the Hub transport --> Send Connectors: I modified the current connector properties using the network tab to route mail through the following smart hosts: and added the ISP's FQDN for their smtp host.

Apply the setting and all done. It was effective immediately.

As suggested it was the easy option alright!

Thank you.

Author Closing Comment

ID: 36990626
The smart host option was a simple fix and a good solution for the outgoing email. The incoming email follows the original path so no drama there. Also there does not appear to be any perceivable delay in delivering mail via the smart host.
Thank you gentlemen – a good result – points split fast response TBone!
(PS second time you have helped me Rob)
LVL 78

Expert Comment

by:Rob Williams
ID: 36992493
Just for future reference with SBS if I'd ALWAYS best to use the wizards. The smart just wizard in the SBS management console earlier us easier and safer.
LVL 78

Expert Comment

by:Rob Williams
ID: 36992494
Just for future reference with SBS if I'd ALWAYS best to use the wizards. The smart just wizard in the SBS management console earlier us easier and safer.

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