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SBS 2008 Exchange Server being Blacklisted

Not a good day :(

I've recently installed an SBS08 server running Exchange 2007 at one of my clients. Today they have been black listed on BARRACUDA BRBL. The server is set to use our ISP's smart-host (mail.opptonline.net) and yet it still has gotten blacklisted. I have confirmed in the Send Connector that the smart host is really really there.

I have attached email headers. When the user send an email. exchange pops back the attached message headers.

Domain.com is my company who is sending the mail which is being blocked.
Keyetv.com is the receiving domain of my blocked mails.
Diagnostic information for administrators:

Generating server: mta1.srv.hcvlny.cv.net (tcp-daemon)

MHunter@keyetv.com
mx2.nexstar.tv (TCP|167.206.4.196|44643|72.249.102.22|25) (barracuda2.nexstar.tv ESMTP [aa0f8fe95058f7c9c41d87fb394acd2f]) #<mx2.nexstar.tv (TCP|167.206.4.196|44643|72.249.102.22|25) (barracuda2.nexstar.tv ESMTP [aa0f8fe95058f7c9c41d87fb394acd2f]) #5.0.0 smtp;554 Service unavailable; Client host [mta1.srv.hcvlny.cv.net] blocked using Barracuda Reputation; http://bbl.barracudacentral.com/q.cgi?ip=96.56.121.10> #SMTP#

Original message headers:

Return-Path: <USER@domain.com>
Received: from tcp-daemon.mta1.srv.hcvlny.cv.net by mta1.srv.hcvlny.cv.net
 (Sun Java System Messaging Server 6.2-8.04 (built Feb 28 2007)) id
 <0L960038R2QOU000@mta1.srv.hcvlny.cv.net>; Wed, 22 Sep 2010 17:08:48 -0400
 (EDT)
Received: from remote.domain.com (mail.domain.com [96.56.121.99])
 by mta1.srv.hcvlny.cv.net
 (Sun Java System Messaging Server 6.2-8.04 (built Feb 28 2007))
 with ESMTP id <0L96003A12QN6KT0@mta1.srv.hcvlny.cv.net> for
 USER@keyetv.com; Wed, 22 Sep 2010 17:08:48 -0400 (EDT)
Received: from DCWSBS08.domain.local ([fe80::842a:a619:3a60:40e4])
 by DCWSBS08.domain.local ([fe80::842a:a619:3a60:40e4%10]) with mapi; Wed,
 22 Sep 2010 17:08:47 -0400
Date: Wed, 22 Sep 2010 17:08:44 -0400
From: Jane Doe <USER@domain.com>
Subject: FW: Post and Pre Logs for Deluxe
To: "USER@keyetv.com" <USER@keyetv.com>
Message-ID: <A947870028054547BFBCBBD69A1D430F37EDD56D@DCWSBS08.dcwcorp.local>
MIME-Version: 1.0
Content-Type: multipart/alternative;
	boundary="Boundary_(ID_+Uh/6Nr3XbRvwhWHvPgpTQ)"
Content-Language: en-US
Importance: high
Accept-Language: en-US
X-Priority: 1
Thread-topic: Post and Pre Logs for Deluxe
Thread-index: ActUPqy8ZLdBvQ1mQ7miHd+tQtynqQBcIsUAATq8UGAAAAgbsA==
acceptlanguage: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
Reporting-MTA: dns; mta1.srv.hcvlny.cv.net (tcp-daemon)

Final-recipient: RFC822; USER@keyetv.com
Action: failed
Status: 5.0.0
Remote-MTA: dns; mx2.nexstar.tv (TCP|167.206.4.196|44643|72.249.102.22|25)
(barracuda2.nexstar.tv ESMTP [aa0f8fe95058f7c9c41d87fb394acd2f])
X-Supplementary-Info: <mx2.nexstar.tv
(TCP|167.206.4.196|44643|72.249.102.22|25) (barracuda2.nexstar.tv ESMTP
[aa0f8fe95058f7c9c41d87fb394acd2f]) #5.0.0 smtp;554 Service unavailable;
Client host [mta1.srv.hcvlny.cv.net] blocked using Barracuda Reputation;
http://bbl.barracudacentral.com/q.cgi?ip=96.56.121.99>

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VCSLI
Asked:
VCSLI
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4 Solutions
 
cmartellCommented:
Your smart host (8.5.1.44) is not blacklisted.  It looks like the culprit IP was 96.56.121.99 but it is not blacklisted now so it looks like Barracuda has delisted the IP and you should be able to send that email now.

You can check your IPs here:
http://www.barracudacentral.org/lookups/ip-reputation

or use the last line in the header
http://bbl.barracudacentral.com/q.cgi?ip=96.56.121.99
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VCSLIAuthor Commented:
I change the IP for the post due to privacy. The real IP is 96.56.121.10. It is Blacklisted.

Barracuda has removed it but now Tiopan has added it.
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cmartellCommented:
Your ip may have been used by a spammer previously if you are bing blacklisted everywhere.  Or possibly your ISP allowed spamming activity and the whole range of IPs is blacklisted.

Herre are instructions to be delisted from Tiopan
http://www.tiopan.com/blacklist.php
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VCSLIAuthor Commented:
I have already emailed them.

The point is, how do i prevent the server from being blacklisted? I thought using a smart-host was enough since email isn't seen as being sent from the server. If i change the PTR, will that help? What shall i change it to? remote.domain.com (mail server address)? If i have to fight daily with blacklists, thats not going to be a good thing...

I can hear angry people already. :(

There has to be a way to prevent this from happening to begin with.
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cmartellCommented:
blacklists go by reputation.  If you are constantly being blacklisted then someone in your organization is spamming or your ISP has a reputation for allowing spamming.  Blacklists can make mistakes but if it happens frequently then you have to do some investigating to find out why.  There is nothing yo can do to prevent being blacklisted other than ensuring that there is no spam originating from your IP.

I suppose you could add an SPF record to your DNS to be sure somebody isn't forging your domain into their spam email headers.
http://www.microsoft.com/mscorp/safety/content/technologies/senderid/wizard/
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VCSLIAuthor Commented:
The network is entirely clean. There are no non domain joined computers on it. All client computers are running fully updated AV software. The setup is less than a week old.
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scraaneCommented:
Well, to be save, if you have a firewall, just block port 25 outgoing. Only open it for your SBS server.

I had a client with up to date AV, but still one desktop was spamming.
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VCSLIAuthor Commented:
Port 25 blocked on all but the server. I enabled logging to tell me which machine is trying to send out on the port. Hopefully this will shed some light if this is indeed the issue. Will post back in a few days.
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cmartellCommented:
There probably isn't anything wrong with your network if it's only a week old.  It culd be that a range of IPs is blacklisted and youre on that range.  If you continue to be blacklisted I would call your ISP.  
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VCSLIAuthor Commented:
Ok well  have blocked port 25 on all outbound traffic except the Exchange server. Will see how things go. Thanks everyone for the advice.
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VCSLIAuthor Commented:
I have not seen anything pop up in the firewall log. It doesn't seem like any computer in the network was ever sending out on port 25. I cant say for sure if its resolved or if we'll be blacklisted again next week. Will have to see how things go. The advice offered was all very well written and well understood, but i dont know if it specifically solved my issue.
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cmartellCommented:
Like I said in my first posts, you "resolve " the issue by going to the RBL website and asking them to delist your IP.  There is nothing else you can do short of getting a new IP (which may not help if you are on a range of black listed IPs) or going to a different ISP.  If the previous owner of your IP was a spammer then you are probably on a bunch of black lists and you will have to request removal as you discover them.
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cmartellCommented:
I provided you with a resolution and you awarded the points to scraane who only gave you a troubleshooting tip to see if there was a problem on your network.  If you had found a problem then you could have taken advice from scraane or someone else to fix it and awarded the points accordingly but there is no problem on your network so as it stands I have provided the only resolution.
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