$Issues with mail flow to new 2010 server in 2003/2010 exchange environment
I am installing exchange 2010 in a windows 2003-based based network, and replacing an existing exchange 2003 server. I have installed the exchange 2010 server, installed SP2, installed a third party SSL cert, etc. Created test mailboxes on the new 2010 server. Can see the 2003 <> 2010 connectors on both 2003 and 2010 server. I can send mail outbound from the test account on 2010 to an external address, but incoming, being routed through the 2003 box that is forward facing, gets stuck in a queue on the 2003 server called "messages queued for delayed delivery". At first, after sending the message it shows queued on the connetor's queue, but then it gets moved to the messages queued for delayed delivery queue.... After a while, this queue shows cleared but nothing is ever delivered to the mailbox on the exchange 2010 box. I have done maybe 10 exchange 2003 > 2010 upgrades, so I am pretty familiar with the process from start to end, and this is the 2nd time I have seen this. The last time it happened, it happened to a co-worker and when I helped him, he had already moved all of the mailboxes, so we just made the 2010 server internet facing and bypassed the 2003 server. I do not have that luxury this time. I have anonymous checked for the receive connector on the 2010 side and I can open a command prompt on the 2003 server and do a manual telnet port 25 call and successfully send a test message to a mailbox on the 2010 side so I am fairly sure the problem lies on the 2003 side. Where to go from here my question ?
April 22nd, 2012 10:35pm

Did you configure a pair of routing group connectors between Exchange 2003 and Exchange 2010, one in each direction?Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
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April 23rd, 2012 12:05am

You're saying that you had a smart host entered on the SMTP virtual server. That would certainly do it because it would block all traffic from Exchange 2003 to Exchange 2010.Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
April 23rd, 2012 6:02pm

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