Hi all,
I am in the process of upgrading from Exchange 2003 to 2013, with 2010 as an intermediate step.
I deployed a new Windows Server 2012 machine with Exchange 2010 SP3. This single server has the Mailbox and Hub Transport roles.
I've moved one test account's mailbox to 2010 prior to doing the whole beefalito for obvious reasons. For awhile, the test account could not send or receive, both to other mailboxes on 2003 or out to the general public. After spending time with Google, I re-built the Routing Group Connectors between 2003 and 2010 (one in each direction). That got me inbound emails from both 2003 users and public servers such as GMail.
The problem is that the 2010 mailbox user cannot send out still. No mail is getting to any of the 2003 users. I've checked connectivity and DNS. I am able to physically telnet into the 2003 server from the 2012 box, send the email manually, and have it be delivered to the 2003 user. Connectivity and SMTP receipt on the 2003 server seem fine. There are no firewalls in play between the two other than Windows firewalls (which have been confirmed to have the requisite ports open), and I've even taken antivirus out of the picture on both servers. I'm pretty confident this is not a network issue (layer 3 or 4).
Here's what I know:
1) In Exchange 2010's Queue Manager, I see the queue in question with the email sitting there. It doesn't fail. The status remains "Active", and it just... sits there.
2) In Exchange 2003's Default SMTP Virtual Server > Current Sessions, I see a connection from the 2010 server. The "Connected Time" just keeps increasing. The session never ends unless I terminate it.
3) Exchange 2003's SMTP logs contain entries for the connection. According to the log, all it sees is three lines: EHLO, x-exps +GSSAPI (whatever that is), and MAIL +FROM:test1@mydomain.com. The next line should be RCPT TO: me@mydomain.com, but it never arrives. Two minutes later, it receives TIMEOUT server.domain.com, followed by QUIT.
So it seems that, again, it's not a networking issue (or so I believe). The connection is established, and data is received. To me, it seems like the Exchange 2010 server is just not finishing the transmission of the message, and both sides just sit there staring at each other.
I have tried uninstalling and reinstalling the Transport Hub role on this server, thinking maybe I corrupted it somehow. Same result. I'm at my wit's end, since Google's no help and I have a nice forehead-shaped dent in my desk.
Thanks in advance for any help you can provide!