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Domain name help - unable to send to some domains RRS feed

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    Trouble sending email to certain domains. It looks like it is forwarding the local domain name causing reverse lookup to fail to resolve to the correct name. New install of Exchange 2010 RU4, on Server 2008 R2. Currently co-existing with a 2003 exchange instance, but it will be removed eventually. Mailbox, CAS, and HUB roles installed on SERVERA. The old 2003 Exchange box is ServerB.  Mail still routes incoming to the Exchange 2003 box, SERVERB, as the NAT’s have not yet been changed on the router. I am unable to specify a FQDN on the send connector of the Hub Transport under organization configuration, as it is grayed out. Is this specified in AD? What am I missing? Any help is greatly appreciated.

     

    NDR 1

    **************************************************************

    Diagnostic information for administrators:

     

    Generating server: wcuserver.wculife.com

     

    emailaddress@att.net

    #< #5.5.0 smtp;550 [PERMFAIL] att.net requires valid sender domain> #SMTP#

     

    Original message headers:

     

    Received: from SERVERA.domain.local ([192.168.1.63]) by SERVERB.domain.local

     with Microsoft SMTPSVC(6.0.3790.4675);   Mon, 9 Aug 2010 15:05:54 -0500

    Received: from SERVERA.domain.local ([::1]) by SERVERA.domain.local

     ([fe80::5c25:c5f1:40ed:58ab%11]) with mapi; Mon, 9 Aug 2010 15:05:54 -0500

     

    **************************************

    NDR2

    Diagnostic information for administrators:

     

    Generating server: wcuserver.wculife.com

     

    emailaddress@etccomputerland.com

    #< #5.5.0 smtp;553 #5.1.8 Domain of sender address <email@servera.domain. local> does not exist> #SMTP#

     

    Original message headers:

     

    Received: from SERVERA.domain.local ([192.168.1.63]) by SERVERB.domain.local

      with Microsoft SMTPSVC(6.0.3790.4675);   Mon, 9 Aug 2010 16:20:03 -0500

    Received: from SERVERA.domain.local ([::1]) by SERVERA.domain.local

      ([fe80::5c25:c5f1:40ed:58ab%11]) with mapi; Mon, 9 Aug 2010 16:07:17 -0500

     

    Monday, August 9, 2010 9:28 PM
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    Grayed out means its a 2003 connector, not a 2010 one.  which is fine for now.  but this means the problem isnt likely related to the 2010 server since, as Jonas mentioned, 2003 is doing both inbound and outbound.

    I'd update the PTR record just for logic sake.  no reason to involve a domain not part of the mail flow.

    Did you visit www.mxtoolbox.com?

    I see you're using postini.  perhaps do outbound through them as well, to offload the administrative burden of IPs and such to them.


    Mike Crowley
    Check out My Blog!

    Tuesday, August 10, 2010 1:26 PM
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    Problem solved. I'm not completely sure the PTR had anything to do with it because when I moved a couple mailboxes back they worked just fine. But it is so odd because Exchange14 was sending our through the 2003 box.. Anyways what fixed it was creating a new send connector to point Exchange14 directly to the internet instead of using the SMTP connector on Ex2003. Thanks for your help and time guys..

     

     

    edit** Do i mark as answer to close this thread?

    Tuesday, August 10, 2010 8:17 PM
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    Are you using send as, or anything less than normal email from outlook and MAPI?

    do you have a valid MX record for your domain?  Please visit mxtoolbox and run the supertool.

    Finally, enable protocol logging on your send connector and paste here the relevant lines dealing with a submission to this domain. 


    Mike Crowley
    Check out My Blog!

    Tuesday, August 10, 2010 2:14 AM
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    If you haven't changed anything the mail will route both in and out through the 2003 server

     

    Update us on the thread about the MX info Mike wrote about and the logging

    Jonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog
    Tuesday, August 10, 2010 11:21 AM
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    No send as, just users sending from their own account.

    I am unable to enable protocol logging, as that box is grayed out as well as the specify FQDN. This is the only send connector I have, and is under the organization level. There are no send connectors under the Server Config,  hub transport. Am I missing where I should enable the logging at?

    The reverse lookup is a little odd to me. Our main domain name is wculife.org, but the reverse is showing wcu1.westerncatholicunion.org. We also own this domain, but it is not the domain associated with our emails. Should this be changed? It has been like this for 6+ years, and has never been an issue until I installed Exchange 2010. Thank you much for your time/help


    a:mail.wculife.org            a 

    Type    Domain Name    IP Address    TTL
    A    mail.wculife.org    216.138.22.51    60 min
    reverse lookup    smtp diag    port scan    blacklist

    Reported by ns.adams.net on Tuesday, August 10, 2010 at 8:01:34 AM (GMT-5)

    Type    IP Address    Domain Name    TTL
    PTR    216.138.22.51    wcu1.westerncatholicunion.org    4 hrs
    reverse lookup    smtp diag    port scan    blacklist

    Reported by ns.adams.net on Tuesday, August 10, 2010 at 8:02:16 AM (GMT-5)
    Tuesday, August 10, 2010 1:16 PM
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    Grayed out means its a 2003 connector, not a 2010 one.  which is fine for now.  but this means the problem isnt likely related to the 2010 server since, as Jonas mentioned, 2003 is doing both inbound and outbound.

    I'd update the PTR record just for logic sake.  no reason to involve a domain not part of the mail flow.

    Did you visit www.mxtoolbox.com?

    I see you're using postini.  perhaps do outbound through them as well, to offload the administrative burden of IPs and such to them.


    Mike Crowley
    Check out My Blog!

    Tuesday, August 10, 2010 1:26 PM
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    Are you using a 3rd part mailwasher or do you receive the mails directly to the company and in?

    I did a check for your domain agains mxtoolbox.com

    100    wculife.org.s6a1.psmtp.com    64.18.5.10

    64.18.5.10 should point back to wculife.org.s6a1.psmtp.com

    Normally this is done by contacting the ISP, they can help you with this

    Jonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog
    Tuesday, August 10, 2010 1:26 PM
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    Yes I did visit mxtoolbox, and used the supertool, that is where the paste output came from on the pointer and reverse lookup.

    I'll ask the ISP to update the pointer record.

    Tuesday, August 10, 2010 1:45 PM
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    Yes we are using Postini for antispam. 64.18.5.10 points to Postini.
    Tuesday, August 10, 2010 1:47 PM
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    Ok, give your ISP a call and update us then it's done
    Jonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog
    Tuesday, August 10, 2010 1:52 PM
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    I contacted the ISP, waiting on a response.

    For the pointer record

    Type    IP Address    Domain Name    TTL
    PTR    216.138.22.51    wcu1.westerncatholicunion.org    4 hrs
    reverse lookup    smtp diag    port scan    blacklist

     

    what does wcu1 refer to? Is that a placeholder or what? I've never seen wcu1 referenced anywhere besides this record.

    **Found out this was an old server before my time here. Not sure why everything worked with the bad pointer record before, and now that the mailboxes are moved to Exchange 2010 and routing through the 2003 box they are failing the reverse lookup.

    • Edited by bain64 Tuesday, August 10, 2010 2:49 PM add content
    Tuesday, August 10, 2010 2:02 PM
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    ISP is quick to respond, love it! Here is the response from them

    "

    "We can change this for you to 'wcuserver.wculife.org'.

     

    The existing PTR record was based on an old setup.

     

    Note that the server answers with a ".com" hostname....

     

     

    Connected to wcu1.westerncatholicunion.org (216.138.22.51).

    Escape character is '^]'.

    220 wcuserver.wculife.com Microsoft ESMTP MAIL Service, Version:

    6.0.3790.4675 ready at  Tue, 10 Aug 2010 09:23:56 -0500"

     

    How can I get the exchange server to respond with the external domain wcuserver.wculife.org instead of the internal wcuserver.wculife.com ?

     

    TY guys so much

    Tuesday, August 10, 2010 2:35 PM
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    Does your Exchange send the mail out directly or are they routed through Postini server?
    Jonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog
    Tuesday, August 10, 2010 2:55 PM
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    Directly. The connector on the 03 box says to use DNS to route to each address space.

    *edit. And there are no routing groups

    • Edited by bain64 Tuesday, August 10, 2010 3:05 PM add
    Tuesday, August 10, 2010 3:02 PM
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    Pointer records appear to be updated, but i still get

    #< #5.1.0 smtp;550 5.1.0 Invalid sender domain> #SMTP#

     

     

     

    ptr:216.138.22.51                ptr 

    Type    IP Address    Domain Name    TTL
    PTR    216.138.22.51    wcuserver.wculife.org    60 min
    reverse lookup    smtp diag    port scan    blacklist

    Reported by lx.adams.net on Tuesday, August 10, 2010 at 10:52:18 AM (GMT-5)

    TELNET RESPONSE

    220 wcuserver.wculife.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 r
    eady at  Tue, 10 Aug 2010 09:53:59 -0500

    When I telnet to SMTP, should it respond with the external domain name?  It is responding with .com, which is our internal.

    • Edited by bain64 Tuesday, August 10, 2010 3:56 PM formatting
    Tuesday, August 10, 2010 3:56 PM
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    Sorry for the triple post, but i'm still stuck and begging for help. Below is the log of an email send that gets bounced. Not sure if it will help but just trying to post everything relevant.

    #Software: Microsoft Internet Information Services 6.0
    #Version: 1.0
    #Date: 2010-08-10 16:48:58
    #Fields: time c-ip cs-method cs-uri-stem sc-status
    16:48:58 64.18.1.73 HELO - 250
    16:48:58 64.18.1.73 MAIL - 250
    16:48:58 64.18.1.73 RCPT - 250
    16:48:58 64.18.1.73 DATA - 250
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 EHLO - 0
    16:48:58 192.168.1.63 - - 0
    16:48:58 64.18.1.73 QUIT - 240
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 MAIL - 0
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 RCPT - 0
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 XEXCH50 - 0
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 BDAT - 0
    16:48:58 192.168.1.63 - - 0
    16:48:58 192.168.1.63 QUIT - 0
    16:48:58 192.168.1.63 - - 0
    Tuesday, August 10, 2010 4:51 PM
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    Problem solved. I'm not completely sure the PTR had anything to do with it because when I moved a couple mailboxes back they worked just fine. But it is so odd because Exchange14 was sending our through the 2003 box.. Anyways what fixed it was creating a new send connector to point Exchange14 directly to the internet instead of using the SMTP connector on Ex2003. Thanks for your help and time guys..

     

     

    edit** Do i mark as answer to close this thread?

    Tuesday, August 10, 2010 8:17 PM
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