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Upgraded 2003 to 2010 - Mail Flow Problems

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  • Upgraded 2003 to 2010 - Mail Flow Problems

    Just done an install of 2010 to upgrade my 2003 box.

    Did the inastall of 2010 fine and got it up and running (pointing it to my 2003 server as the legacy server). Works fine but when I move a mailbox to the new server the mail flow (in and out as well as between servers) stops working.

    On 2003 server, internet and internal mail flows in and out as well as Activesync working fine still for my iPhone users.

    I changed the MX records on the domain to point to the new 2010 server (all DNS is correct - I have full control of the DNS servers) and added a send connector on the 2010 box for SMTP.

    Also instaled SAN certificate to the server which went fine.

    I moved a test mailbox over to the 2010 box to test and have been unable to send or receive (either internet mail or between the 2010 mailbox and legacy 2003 mailboxes).

    With MX pointing at the 2010 server internet mail to 2003 legacy mailboxes also fails now.

    Change the MX records back to the 2003 server and everything (on the 2003 box) works fine again.

    I need to get internet mail flowing to and from the 2010 box (including Activesync for iPhone users) and get mail flowing between the 2003 and 2010 box until I can decomission the legacy server.

    I'm sure there are guides online somewhere, but this if my first 2010 exposure and I am not really sure what I am looking for.

    I have to get this working by the time my company starts back next week and unfortunately due to financial constraints training and consultancy are not (and never have been) options. We purchased the upgrade before we had to tighten our belts and not they want to see it implemented.

    Any help or pointers to where to get help would be much appreciated.

    Any other info needed to help someone help me then please ask and I will post.

  • #2
    Re: Upgraded 2003 to 2010 - Mail Flow Problems

    Anyone?

    Thanks

    Comment


    • #3
      Re: Upgraded 2003 to 2010 - Mail Flow Problems

      Its been less than 24 hours since you posted your question.

      People on these forums give up their free time to help out others in need of assistance. Please be mindful of this when asking questions.

      It is also a holiday in some parts of the world and as such our Exchange experts could possibly be away and unable to answer your question.

      If you need an immediate answer then your best bet is to call Microsoft direct and raise a support call with them, which they will charge you for unless you have the correct support contract.

      Comment


      • #4
        Re: Upgraded 2003 to 2010 - Mail Flow Problems

        Are you able to telnet to you new Exchange 2010 box on port 25 from both internal and external???

        Does internal mail work???

        Comment


        • #5
          Re: Upgraded 2003 to 2010 - Mail Flow Problems

          He says internal mail does not work -- worrying since it should be "out of box" on a Exchange 2010 install to an existing organisation.

          Have you enabled anonymous receive on the default 2010 receive connector?
          Can you telnet the Exchange 2010 box from 2003?
          Tom Jones
          MCT, MCSE (2000:Security & 2003), MCSA:Security & Messaging, MCDBA, MCDST, MCITP(EA, EMA, SA, EDA, ES, CS), MCTS, MCP, Sec+
          PhD, MSc, FIAP, MIITT
          IT Trainer / Consultant
          Ossian Ltd
          Scotland

          ** Remember to give credit where credit is due and leave reputation points where appropriate **

          Comment


          • #6
            Re: Upgraded 2003 to 2010 - Mail Flow Problems

            Apologies for my apparent impatience. Calling MS is not an option - my company will not pay for it - I thought with it being a working day in most places and the forum being so busy someone might be around.

            I have already enabed anonymous on the default receive connector.

            Just been doing some more testing.

            2k3 user to 2k10 user: OK
            Internet to 2k10 user: OK
            2k10 user to 2k3 user: FAIL
            2k10 user to Internet: FAIL

            I can telnet from any LAN machine to either the 2k3 or 2k10 boxes on port 25 and can also telnet to 25 from the internet.

            Does this give any clues?

            Comment


            • #7
              Re: Upgraded 2003 to 2010 - Mail Flow Problems

              So inbound is OK but outbound is blocked

              Can you confirm you have send connectors (org-config / hub transport node in EMC) and what their properties are
              Tom Jones
              MCT, MCSE (2000:Security & 2003), MCSA:Security & Messaging, MCDBA, MCDST, MCITP(EA, EMA, SA, EDA, ES, CS), MCTS, MCP, Sec+
              PhD, MSc, FIAP, MIITT
              IT Trainer / Consultant
              Ossian Ltd
              Scotland

              ** Remember to give credit where credit is due and leave reputation points where appropriate **

              Comment


              • #8
                Re: Upgraded 2003 to 2010 - Mail Flow Problems

                Originally posted by Ossian View Post
                So inbound is OK but outbound is blocked

                Can you confirm you have send connectors (org-config / hub transport node in EMC) and what their properties are
                Thanks for the reply. Please see below:

                Default Send Connector (created by me)

                General
                Protocol Logging: None
                FQDN: mail.mydomain.com (the one which my MX record points to)
                Max Message Size: 10240

                Address Space (SMTP is the only one)
                Address Space: *
                Include Subdomains: Yes
                Cost: 1

                Network
                Use DNS MX records to route mail: Yes

                Source Server
                Only one listed is my 2k10 server


                Outbound ? Problem Domains (carried over automatically from my 2k3 server)

                I am unable to disable this to test. Trying to disable give the following error:

                Action 'Disable' could not be performed on object 'Outbound - Problem Domains'.

                Outbound - Problem Domains
                Failed
                Error:
                Property Enabled can't be set on this object because it requires the object to have version 0.1 (8.0.535.0) or later. The object's current version is 0.0 (6.5.6500.0).


                General
                All blank or set to none - all greyed out

                Address Space
                Multiple listings for domains we used to have problems delivering mail to for one reason or another ? each is SMTP with the domain (for example yahoo.com) as the address space and a cost of 1

                Network
                Use DNS MX records to route mail: Yes

                Source Server
                None listed

                Comment


                • #9
                  Re: Upgraded 2003 to 2010 - Mail Flow Problems

                  I know it's the holidays but I would really appreciate any help or advice on this. Wanted to be up and running when work starts back tomorrow.

                  Comment


                  • #10
                    Re: Upgraded 2003 to 2010 - Mail Flow Problems

                    Is anyone around today that might be able to offer help?

                    It seems like it is something so simple but I just can't figure it out.

                    Thank you in advance

                    Comment


                    • #11
                      Re: Upgraded 2003 to 2010 - Mail Flow Problems

                      If you use the message flow tool in Ex10, does it show you where the mail tries to go?
                      Please do show your appreciation to those who assist you by leaving Rep Point https://www.petri.com/forums/core/im.../icon_beer.gif

                      Comment


                      • #12
                        Re: Upgraded 2003 to 2010 - Mail Flow Problems

                        As the error message regarding the accepted domain indicates those accepted domains have to be upgraded in order to administer them using Exchange 2010 tools.
                        You could achieve this using either EMC or powershell, a simple get-accepteddomain | set-accepteddomain should do the trick.

                        Is your problem sending for 2k10 mailboxes to 2k3 mailboxes and the internet still actual?
                        If yes, can you provide any NDR or other helpful information?

                        Comment


                        • #13
                          Re: Upgraded 2003 to 2010 - Mail Flow Problems

                          Originally posted by FischFra View Post
                          As the error message regarding the accepted domain indicates those accepted domains have to be upgraded in order to administer them using Exchange 2010 tools.
                          You could achieve this using either EMC or powershell, a simple get-accepteddomain | set-accepteddomain should do the trick.

                          Is your problem sending for 2k10 mailboxes to 2k3 mailboxes and the internet still actual?
                          If yes, can you provide any NDR or other helpful information?
                          I now have mail working as follows:

                          2k3 to 2k10 - OK
                          2k3 to Internet - OK
                          2k10 to 2k3 - FAIL
                          2k10 to Internet - OK

                          It was a mix of antivirus and reverse DNS that was causing the internet mail issue (simple but easy to overlook).

                          My next problem is getting mailflowing from 2k10 to 2k3. The 2k10 to 2k3 failures give me an undeliverable as follows now though (let me know if anything else will be helpful in diagnosing):

                          For info to read the below:
                          [email protected] .com is me (with a mailbox on the 2k3 server)
                          [email protected] (a mailbox on the 2k10 server)
                          emerald is my 2k10 server (on internal ip 192.168.1.10)
                          peridot is my 2k3 server (on internal IP 192.168.1.3)

                          Code:
                           
                          Delivery has failed to these recipients or groups:
                           
                          My Name mailto:[email protected] 
                          There's a problem with the recipient's mailbox. Please try resending this message. If the problem continues, please contact your helpdesk. 
                           
                          Diagnostic information for administrators:
                           
                          Generating server: peridot.sheffieldfutures.org.uk
                           
                          [email protected] 
                          #< #5.2.1> #SMTP#
                           
                          Original message headers:
                           
                          Received: from emerald.mydomain.com ([192.168.1.10]) by
                          peridot.sheffieldfutures.org.uk with Microsoft SMTPSVC(6.0.3790.4675); Wed,
                          4 Jan 2012 10:56:05 +0000
                          Received: from emerald.mydomain.com([fe80::6cdd:a494:37f1:3b49])
                          by Emerald.mydomain.com([fe80::6cdd:a494:37f1:3b49%14]) with mapi
                          id 14.01.0355.002; Wed, 4 Jan 2012 10:56:05 +0000
                          Content-Type: application/ms-tnef; name="winmail.dat"
                          Content-Transfer-Encoding: binary
                          From: Test User [email protected]
                          To: =?iso-8859-1?Q?Me?=
                          [email protected]
                          Subject: 2k10 to 2k3
                          Thread-Topic: 2k10 to 2k3
                          Thread-Index: AczKz3Qz4vIjxr8WSQeO39SmcIuQNg==
                          Return-Receipt-To: [email protected]
                          Date: Wed, 4 Jan 2012 10:56:04 +0000
                          Message-ID: [email protected]
                          Accept-Language: en-US
                          Content-Language: en-US
                          X-MS-Has-Attach:
                          X-MS-TNEF-Correlator: [email protected]
                          MIME-Version: 1.0
                          X-Originating-IP: [192.168.1.52]
                          Return-Path: [email protected]
                          X-OriginalArrivalTime: 04 Jan 2012 10:56:05.0361 (UTC) FILETIME=[74CE2610:01CCCACF]

                          Comment


                          • #14
                            Re: Upgraded 2003 to 2010 - Mail Flow Problems

                            So your 2k3 server is generating the NDR right now, you should configure the connection log at the virtual SMTP server at your 2k3 box and look if any helpful information comes along.

                            A good first test would be initiating a telnet session from your 2k10 server to the 2k3 server at port 25 and trying to send a mail manually:

                            telnet peridot.sheffieldfutures.org.uk 25
                            helo ...
                            mail from: [email protected]
                            rcpt to:
                            [email protected]
                            data
                            Subject: Test
                            Test
                            .


                            Comment


                            • #15
                              Re: Upgraded 2003 to 2010 - Mail Flow Problems

                              Originally posted by FischFra View Post
                              So your 2k3 server is generating the NDR right now, you should configure the connection log at the virtual SMTP server at your 2k3 box and look if any helpful information comes along.

                              A good first test would be initiating a telnet session from your 2k10 server to the 2k3 server at port 25 and trying to send a mail manually:

                              telnet peridot.sheffieldfutures.org.uk 25
                              helo ...
                              mail from: [email protected]
                              rcpt to:
                              [email protected]
                              data
                              Subject: Test
                              Test
                              .


                              Thank you for the reply

                              Email from Telnet - 2k10 to 2k3 worked fine! Although it went to junk mail folder.

                              Mail from Outlook user with 2k10 mailbox fails wih NDR above!

                              Not sure if this helps diagnose!

                              Comment

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