Cannot send email following upgrade to Exchange 2010 RRS feed

  • Question

  • The original Exchange 2007 environment consists of one server residing outside the trusted network that hosts the Edge role and one server inside the trusted network that hosts the Client Access, Hub Transport, and Mailbox Server roles. We also have McAfee (formerly MXLogic) as third party email filter/forwarder, setup via a Smart Host in the Exchange 2007 environment.


    We currently have implemented an Exchange 2010 server (hosting CAS, Hub, and Mailbox roles) that resides inside our trusted network and is coexisting with the original Exchange 2007 server. Our plan is to migrate all mailboxes, Global Address List, Public Folders, etc to the new 2010 server and then decommission the old 2007 server. We also plan to take the Edge server out of the mix, configuring the primary server to communicate directly with McAfee for external mail flow.


    Our primary domain is, and the secondary domain is Since installing the coexisting 2010 server in our environment, the accounts cannot send email, but they can receive from both internal ( and external (ex. addresses. addresses send and receive with no issues, both internally and externally.


    For testing, we have moved one mailbox and two mailboxes over to the Exchange 2010 server.


    While testing, we changed the following internal DNS entries to point to the 2010 server:,, and  We also changed our firewall rule for https traffic (OWA) to point to the new 2010 server. During this testing, accounts could not send or receive. After changing the DNS and firewall configuration back to the original 2007 sever, they could receive but not send externally. Unfortunately I do not recall the behavior of the accounts, as we focused on the accounts when testing last night.


    To give you an idea of how things transpired, we started by making the DNS and firewall changes. We then created a self-signed certificate on the new Exchange 2010 server. At that point we could not send or receive external mail from either or We could see the messages in the queue of the Edge server. We then rebooted the Edge server, and after it came up, the queue spooled out successfully and could then send and receive externally. However, still could not send or receive. Next, we changed the DNS and firewall configuration to point back to the original Exchange 2007 server, and could receive but  not send to external addresses.


    As further information, when we make the DNS and firewall changes to point to the 2010 server, OWA works as expected. Internally, if you connect to the 2007 server’s IP, you can log in whether your mailbox resides on the 2007 or 2010 server. The same is true of the 2010 server. If the mailbox resides on the opposite server than which you connect, you are redirected to the server which houses your mailbox. Externally, if you connect to you get the proper login interface of the 2010 server. If your mailbox resides on the 2010 server, you access the mailbox. If your mailbox resides on the 2007 server, it loses the connection when it tries to redirect you to the other mailbox (as expected), since the machine name of the 2007 server is not publically advertised.


    Monday, October 22, 2012 4:28 PM

All replies

  • Hi Jeff.  I don't know if you already did this, but a better place to post this would have been the admin group, rather than the development one.  Developers don't always make good admin troubleshooters.  Of course, you've probably fixed this issue by now. It might be worth mentioning that E2010 does not create a send connector by default at install time, but why it can't route through your existing E2007 one, I can't tell from the above.

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    Wednesday, October 24, 2012 3:58 PM