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SBS 2008 Exchange 2007 550 5.7.1 Unable to relay

Posted on 2011-02-28
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Last Modified: 2012-08-13
I have an SBS 2008 Exchange 2007 server.  The server is rejecting mail with an Unable to relay 550 5.7.1 error.  The mail client we use us Outlook 2010.

I am not sure where to begin to resolve this, but I have an AE who is complaining like mad.

I have insured the DNS and rDNS is correct following demazter article and suggestions.

I can't seem to find anything on this in the knowledge base.

Below is the bounceback:

Hi. This is the qmail-send program at gateway05.websitewelcome.com.
I'm afraid I wasn't able to deliver your message to the following addresses.
This is a permanent error; I've given up. Sorry it didn't work out.

<tgatti@blacktwigllc.com>:
65.107.75.230 does not like recipient.
Remote host said: 550 5.7.1 Unable to relay
Giving up on 65.107.75.230.

--- Below this line is a copy of the message.

Return-Path: <john.mandelker@cutexbrands.com>
Received: (qmail 21478 invoked from network); 25 Feb 2011 21:33:13 -0000
Received: from argenta.websitewelcome.com (174.120.172.130)
 by gateway05.websitewelcome.com with SMTP; 25 Feb 2011 21:33:13 -0000
Received: from [99.59.137.153] (port=29827 helo=[192.168.1.102])
            by argenta.websitewelcome.com with esmtpsa (TLSv1:AES128-SHA:128)
            (Exim 4.69)
            (envelope-from <john.mandelker@cutexbrands.com>)
            id 1Pt5L3-00034X-1n
            for tgatti@blacktwigllc.com; Fri, 25 Feb 2011 15:36:37 -0600
From: John Mandelker <john.mandelker@cutexbrands.com>
Mime-Version: 1.0 (Apple Message framework v1082)
Content-Type: multipart/alternative; boundary=Apple-Mail-18-387529709
Subject: Re: Test Email
Date: Fri, 25 Feb 2011 15:36:33 -0600
In-Reply-To: <ADE651B3CB09BA4F964A4C64FB5736B5286BF6D26D@SBS.btc.local>
To: Tom Gatti <tgatti@blacktwigllc.com>
References: <ADE651B3CB09BA4F964A4C64FB5736B5286BF6D26D@SBS.btc.local>
Message-Id: <624DDBE3-4193-4E49-916E-3FF1062AE860@cutexbrands.com>
X-Mailer: Apple Mail (2.1082)
X-AntiAbuse: This header was added to track abuse, please include it with any abuse report
X-AntiAbuse: Primary Hostname - argenta.websitewelcome.com
X-AntiAbuse: Original Domain - blacktwigllc.com
X-AntiAbuse: Originator/Caller UID/GID - [47 12] / [47 12]
X-AntiAbuse: Sender Address Domain - cutexbrands.com
X-Source:
X-Source-Args:
X-Source-Dir:



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Question by:blacktwig
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19 Comments
 
LVL 9

Expert Comment

by:TBK-Consulting
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At first glance and looking at the recipient ip address for blacktwigllc.com it appears as if the receiving server in this case is setup incorrectly and not accepting the emails ...
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Author Comment

by:blacktwig
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Not sure of what you are referring to.  Can you elaborate further?

We receive an average of 30,000 emails a month with one to three issues of this sort.  

In the bounceback message i see the mail comes is addressed from a domain that is sent from a different domain.  Isn't that relaying mail?

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Expert Comment

by:TBK-Consulting
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yes that is what relaying mail is and most servers are set to NOT receive this for spam reasons ... as most spam is sent this way ... you can set the server to receive no matter what from specific ip addesses or domains - i am sorry tho I forget at the moment exactly where to set this ... but once set you should be able ot receive legit mail from places that are improperly setup to send correctly ... Personally however, I'd talk to the sending IT Department and let them know they have an issue if they are relaying mail thru a different server without proper DNS Records setup to support that ... their rDNS should be setup or at the very least instead of relaying they should use a smarthost ...
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Akhater earned 500 total points
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why are you assuming this problem is from your side? is this error when ppl are sending you emails or when you are sending to someone ?



is this your domain ? blacktwigllc.com


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Author Comment

by:blacktwig
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Yes, blacktwig is my domain.  I have a partner and an AE who are questioning my abilities and they believe this is my error and that I need to fix it.  I don't believe it is on our end, but I'm not an expert so I wanted to get advice from those who are smarter than I.  Everything I'm reading and looking at tells me this is on the senders side and I have to prove it's not mine, but i still have to make our server accept this mail without opening the flood gates to spammers.  I'm not sure I know how.

I have explained to the partners that the mail is, from what i know, relayed, and that the the blacktwig server is set not to accept relayed mail which i believe is the industry standard.  The blacktwig server's configuration is pretty much just the defaulted setup.

The assistance you guys are providing is great.  Thanks for anything you can advise or tell me what to do.

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Author Comment

by:blacktwig
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Sorry Akhater,  i forgot to mention that the sender receives this when the email is sent to us.
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LVL 49

Expert Comment

by:Akhater
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there is something very weird in your case

<tgatti@blacktwigllc.com>:
65.107.75.230 does not like recipient.
Remote host said: 550 5.7.1 Unable to relay
Giving up on 65.107.75.230.

clearly says that 65.107.75.230 is refusing emails for tgatti@blacktwigllc.com

however I have tlenet to this server (obviously your sbs) and sent you a test email and it went fine do you have any kind of anti spam ?
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Author Comment

by:blacktwig
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yes, we use sunbelt-software's vipre.

Can you elaborate what is "weird"?  

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LVL 49

Expert Comment

by:Akhater
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The weird part is that, depending on the NDR, exchange is sending an unable to relay message for its own domain which is very very weird, so I have to tend to beleive it is the antispam software
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Author Comment

by:blacktwig
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I see, I'll need to contact Sunbelt then and see what they think.  That's what I didn't understand or was confused by the NDR as that the IP Address was reporting back.
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Expert Comment

by:Akhater
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is it always happening with the same sender or sometmes the same sender passes and sometimes no ?
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Author Comment

by:blacktwig
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It seems to be with the same domain, but different clients.  For example, client 1 used tim@domaina.com and client 2 uses john@domainb.com, but the mail is sent through gateway##.websitewelcome.com.

That's why I figured the network admin for those client, which happens to be the same fellow, was causing the mail to be relayed.

I was going to disable the vipre to see if the issue goes away.

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Author Comment

by:blacktwig
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I have disabled Vipre so that no incoming or outgoing mail is being filtered and it still fails with the 550 5.7.1 error.   I have disabled all anti-spam  filtering on the Hub transport also.  I am at a loss.  
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Author Comment

by:blacktwig
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Can rDNS lookup be turned off in Exchange 2007?
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Author Comment

by:blacktwig
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This is what the websitewelcome.com NOC is referring to:  

It still has me confused. MXToolbox is great, isn't it? I would not consider either of those issues to cause this problem. I do see that they have their MX record defined as a CNAME. That is not good, but it doesn't seem to be the problem, either. It is supposed to be an A record.

It's weird that you can send to ds@blacktwigllc.com from gmail, but not websitewelcome. The error happens after websitewelcome sends the "RCPT TO:
ds@blacktwigllc.com" SMTP command. Their server is saying that they can't relay. This is good if the server doesn't recognize the domain of the recipient. This should not be a relay.

I ran a test with telnet from the NOC email gateway server. It did not seem to have this problem. It almost sounds like the To: header is getting their server confused. This is created by the email client.

However, our server is set up as an A record not a CNAME.  Could their DNS be faulty and not caching correctly?
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LVL 49

Expert Comment

by:Akhater
Comment Utility
rDNS will never lead to a "unable to relay" reply but it looks like the problem is from websitewelcome and not from your end

my best guess at this point is that they have some kind of transparent SMTP proxy on their side that is taking the smtp requests but this is just a very wild guess
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Assisted Solution

by:blacktwig
blacktwig earned 0 total points
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Thanks for your input Akhater.  The "issue" has miraculously cease to exist.  So you were quite right that the issue was not on my server, but was with the clients ISP.  I just had to go through all the steps to convince them that the issue was rightfully theirs.  
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LVL 49

Expert Comment

by:Akhater
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thank you for the updates, what is important is that you sorted it out
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Author Closing Comment

by:blacktwig
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none
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