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05.09.2008 at 03:36PM PDT, ID: 23391005 | Points: 250
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Attachment Details
5.5.0 550 SMTP Communication Issues
Tags: Microsoft, Exchange, 2003
I manage an Exchange 2003 server for a client who has lately been receiving similar errors to what is shown below.

Your message did not reach some or all of the intended recipients.

      Subject:  FW: Programmer/Analyst

      Sent:     5/9/2008 2:47 PM


The following recipient(s) could not be reached:

      "someusername"@earthlink.net on 5/9/2008 2:46 PM

            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.

            <mail.clientdomain.com #5.5.0 smtp;550 550 Dynamic/zombied/spam IPs blocked.




Most of the emails go out just fine, but some get rejected simialr to this.

Their MX record points to mail.clientdomain.com. However they do use a Barracuda Spam Filter, which has the name barracuda.clientdomain.com

Their DSL router forward the static IP, associated with the MX record, on port 25 to the Barracuda device, which has a private IP address 192.168.1.50. That then forwards to the Exchange server bearing IP address 192.168.1.200

Any ideas as to why they're getting blocked?

BTW their domain nor IP is on any SPAM Blacklist that I can see.
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Question Stats
Zone: Networking
Question Asked By: cfgchiran
Question Asked On: 05.09.2008
Participating Experts: 2
Points: 250
Views: 0
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05.09.2008 at 03:49PM PDT, ID: 21536877

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05.09.2008 at 03:51PM PDT, ID: 21536883

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05.09.2008 at 04:22PM PDT, ID: 21537010

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05.09.2008 at 04:25PM PDT, ID: 21537034

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05.09.2008 at 04:31PM PDT, ID: 21537085

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05.09.2008 at 04:48PM PDT, ID: 21537198

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05.09.2008 at 05:34PM PDT, ID: 21537343

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05.09.2008 at 11:50PM PDT, ID: 21538066

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05.10.2008 at 05:22AM PDT, ID: 21538711

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05.14.2008 at 09:00AM PDT, ID: 21565586

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05.14.2008 at 04:24PM PDT, ID: 21569510

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05.14.2008 at 05:24PM PDT, ID: 21569781

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05.14.2008 at 05:26PM PDT, ID: 21569785

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05.14.2008 at 06:20PM PDT, ID: 21569992

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05.15.2008 at 04:53PM PDT, ID: 21578872

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05.15.2008 at 06:57PM PDT, ID: 21579318

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05.16.2008 at 04:21PM PDT, ID: 21587154

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05.16.2008 at 05:23PM PDT, ID: 21587493

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05.09.2008 at 03:49PM PDT, ID: 21536877

Rank: Master

Can you do some checks on www.intodns.com and do a diagnostics on www.mxtoolbox.com ?

Let us know what happened ok?

Richard.
 
05.09.2008 at 03:51PM PDT, ID: 21536883

Rank: Master

Found this link as well. It could be Earthlink:
http://vincentcollins.com/2008/02/07/earthlink-and-550-dynamiczombiedspam-ips-blocked/

Hope this helps.

Richard.
 
05.09.2008 at 04:22PM PDT, ID: 21537010
Thanks for the responses.

I did the mxtoolbox.com tests for Blacklisting and the IP was not blacklisted. The diagnostic gave me the results below (domain name and IP have been modified)

The results from IntoDNS is in the attached PDF.

RESULT: mail.clientdomain.com
Banner: barracuda.clientdomain.com ESMTP (bd4cff2118125c8dfd1b57cfcff5f338) [375 ms]  
Connect Time: 2.047 seconds - Good
Transaction Time: 2.672 seconds - Good
Relay Check: OK - This server is not an open relay.
Rev DNS Check: OK - 70.x.x.x resolves to mail.clientdomain.com
GeoCode Info: Geocoding server is unavailable
Session Transcript: HELO mxtoolbox.com - DIAGNOSTIC TEST - See http://www.mxtoolbox.com/Policy.aspx
504 Command parameter not implemented [47 ms]
HELO mxtoolbox.com
250 barracuda.clientdomain.com Hello mxtb-pws1.mxtoolbox.com [64.20.227.131], pleased to meet you [62 ms]
MAIL FROM: <test@mxtoolbox.com>
250 Ok [47 ms]
RCPT TO: <test@mxtoolbox.com>
550 No such domain at this location (test@mxtoolbox.com) [47 ms]
QUIT
221 Bye [47 ms]


Thank you.
 
DNS Results
 
 
05.09.2008 at 04:25PM PDT, ID: 21537034

Rank: Master

Looks good overall.

Can you contact Earthlink and ask them if they can check if you're blocked ?(see my 2nd post).

Richard,
 
05.09.2008 at 04:31PM PDT, ID: 21537085
Thanks Richard, I'll do so. I did notice in the MXToolbox diagnostic, right at the end of the report it says "550 No such domain found."

Is this something to be concerned about?

Also is it necessary to have a PTR for the Barracuda mail filter? Cause I am wondering if the reverse DNS verification is sent on port 25, the response is going to be from the Barracuda and not the Exchange server, and it will advertise itself as "barracuda.clientdomain.com" and not "mail.clientdomain.com"

Thanks.
 
05.09.2008 at 04:48PM PDT, ID: 21537198

Rank: Master

>> it will advertise itself as "barracuda.clientdomain.com" and not "mail.clientdomain.com
Sounds logical. Because it will reverse the external ip and wants to find mail.cliendomain.com but finds barracuda.clientdomain.com.

>> 550 No such domain found."
I think this is also related to this reverse DNS on barracuda.cliendomain.com

Did this config worked before or is this a clean and new install?

Richard.
 
05.09.2008 at 05:34PM PDT, ID: 21537343
Richard.

Thanks for the response. It's always been like this and has always worked. But lately we've received this messages.

Is the fact that the reverse DNS is stating barracuda.clientdomain.com instead of mail.... and issue for PTR?
 
05.09.2008 at 11:50PM PDT, ID: 21538066

Rank: Master

>> Is the fact that the reverse DNS is stating barracuda.clientdomain.com instead of mail.... and issue for PTR?

Sorry I don't understand your question.

Can your mailserver be resolved through the barracuda? can you do a telnet through the barracuda to the mailserver?

Richard.
 
05.10.2008 at 05:22AM PDT, ID: 21538711

Rank: Sage

>>mail.clientdomain.com #5.5.0 smtp;550 550 Dynamic/zombied/spam IPs blocked.

You can't get more straight forward than that - I would wager that you are on a spam list, but not necessarily an open spam list.

Earthlink has you blacklisted for one of a handful of reasons; either they a) received a ton of spam from your IP, or range, b) you have a dynamic IP and your ISP sold you out (which we know isn't the case),  c) your ip has been pegged as a zombie (virus) or d) you are horrendously misconfigured with the barracuda in there/

What domains can't you email?  Earthlink, Gmail, AOL, etc?  Got any other errors like the above?

Kieran
 
05.14.2008 at 09:00AM PDT, ID: 21565586
Sorry for the delay. Telnet is not configured or allowed into the servers through the Firewall. But email comes into the Exchange just fine through the Barracuda.

I guess what I meant by the PTR is, that the exchange server is named mail.clientdomain.com and the barracuda is named barracuda.clientdomain.com

Our PTR is set for the IP MX record to resolve to mail.clientdomain.com

However if a verification request is sent by an Earthlink mail server to that ip address of our MX record, it will be forwarded to the Barracuda unit first, and I guess the Barracuda might respond saying that its name is barracuda.clientdomain.com and not mail.clientdomain.com

Could that be an issue?

In answer to the last posting, we have had some issues getting to Craigslist.org, but not all the time. Occassionally AOL too.
 
05.14.2008 at 04:24PM PDT, ID: 21569510

Rank: Sage

>>Could that be an issue?

I doubt it - think of places like GMail - their sending servers are not the same as their receiving servers.

What issues did you have going to craigslist and aol?  Do you have any old bounces?
 
05.14.2008 at 05:24PM PDT, ID: 21569781
Good point. I don't have any of the old bounces, but I do know they were all 550 errors.
 
05.14.2008 at 05:26PM PDT, ID: 21569785
Though I do wonder in regards to what you said about gmail - the outgoing and receiving servers maybe different, but all of them may have PTR records right? In my case I only have the MX record PTR to mail.clientdomain.com and nothing for barracuda.clientdomain.com
 
05.14.2008 at 06:20PM PDT, ID: 21569992

Rank: Sage

For receiving, the server must be in the MX records - that is all, you don't need a PTR, you don't need a correct SMTP greeting - nothing - receiving is a right, not a priviledge

Sending is another matter altogether - you must have a PTR, you must have an A record that matches the pointer, you must identify yourself correct - you don't have to be in the MX records.

Send an email from your server to an external server, and post the headers here so we can see what is going on
 
05.15.2008 at 04:53PM PDT, ID: 21578872
Here's the header information (modified to hide the client's actual domain name). One thing to nice might be that the Windows domain (internal) is named clientdomain.local and not a .com name. But even the in-house DNS servers have a record that point the same IP to both mail.clientdomain.local and mail.clientdomain.com

Not sure if that matters.

From Hiran Thu May 15 16:39:06 2008
Return-Path:   <hiran@clientdomain.com>  
Authentication-Results:   mta174.mail.re3.yahoo.com from=clientdomain.com; domainkeys=neutral (no sig)  
Received:   from 70.x.x.x (EHLO mail.clientdomain.com) (70.x.x.x) by mta174.mail.re3.yahoo.com with SMTP; Thu, 15 May 2008 16:46:22 -0700  
MIME-Version:   1.0  
Content-Type:   multipart/alternative; boundary="----_=_NextPart_001_01C8B6E4.DDA7F245"  
Content-class:   urn:content-classes:message  
Subject:   Test  
Date:   Thu, 15 May 2008 16:39:06 -0700  
Message-ID:   <E92BB8100251374B96C8F5BC73FF4568057BA8@MAIL.clientdomain.local>  
Thread-Topic:   Test  
Thread-Index:   Aci25N2ZMlgPKtMRRtOuM+2JtV/1hQ==  
From:   "Hiran" <hiran@clientdomain.com>  Add sender to Contacts  
To:   <hiran****@yahoo.com>  
Content-Length:   635  
 
05.15.2008 at 06:57PM PDT, ID: 21579318

Rank: Sage

That looks pretty good, and no, the .local doesn't make a difference

>>70.x.x.x (EHLO mail.clientdomain.com<<

Can you confirm that 70.x.x.x resolves to mail.clientdomain.com and that resolves back to 70.x.x.x?
 
05.16.2008 at 04:21PM PDT, ID: 21587154
Yes if I do an nslookup for that 70.x.x.x IP I get mail.clientdomain.com (the correc domain) and if I an nslookup for mail.clientdomain.com I do get the same correct 70.x.x.x address.
 
05.16.2008 at 05:23PM PDT, ID: 21587493

Rank: Sage

Well then you don't have an obvious problem with your configuration.

So we are back to looking at bounces - that AOL bounce indicated you are on an AOL Block list, you may have subsequently been removed - got any other bounces for us?  Anything recent?
 
 
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