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Migration from SBS 2003 to SBS 2008 Exchange **URGENT***

Posted on 2010-09-21
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I am in the middle of a migration and there has been some questions about losing emails in the process of migrating mailboxes.  

We have trend-micro spam web service that filters spam from coming into the server. The MX record is setup for the trend micro service. Non-spam email gets forwarded to our server via our firewall that is setup to forward all port 25 traffic to the old server. Should we have the firewall point to our new server or the old one?

Secondly, is there a way to test this before we start the exchange piece?
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Question by:fishbowlstudios
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by:edbonl
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The reason you are losing emails is the spam filter.
While migrating you can better stop all the virusscan an spam tools on all mail servers.

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by:BAYCCS
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If I understand you correctly sounds like you are ready to move your mailboxes over to the new server and you are worried about loosing emails during the migration?

Don't be worried, keep everything pointed at the old server until you are ready to break the smtp connector and offically bring down the old server. Once you break the connector you will have to NAT the firewall from the old to the new.

Are you following Microsoft's Migration Manual?
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by:jebeckham
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Are you performing intra-org moves (i.e., within the same AD forest & Exchange org) and just performing mailbox moves from 2003 to 2007 (moves should be executed from 2007)?  If so, are you able to deliver e-mail between 2003 and 2007 mailboxes?  Check routing group connector in both directions between 2003 and 2007 and check your Internet SMTP connector on 2003.  You should be able to to continue to receive e-mail from the Internet until you're ready to point it to your 2007 server.
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by:fishbowlstudios
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"If I understand you correctly sounds like you are ready to move your mailboxes over to the new server and you are worried about loosing emails during the migration?"
-Yes, that is correct.
"Are you following Microsoft's Migration Manual?"
- Yes we are and it says the first task is to remove internet connectors from the source server. Before we do that, we'd like to test the email flow to make sure everything is functioning correctly before we start moving mailboxes.  So, is everyone saying NOT to remove the SMTP connector until we are ready to decommission the server?
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by:BAYCCS
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Are you sure it is telling you to break the connector first, that doesn't sound right... I would have to look at the migration manual again...

If you want to test mailflow setup a new email box on the 2008 server. Bascially setup a new account. Then try to send mail from the outside, that should tell you that it is working even with the firewall pointing to the old server b/c of the connector.
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by:BAYCCS
BAYCCS earned 200 total points
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Ok I double checked the manual and you are right it does say that. It' been a while...

I would change the NAT on the firewall to point to the new server, break the connector, then move the mailboxes. Exchange is smart enough to hold the messages in the queue until the mailbox is fully moved.
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by:R--R
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The MX is pointed to Trend micro and then from trend micro to old exchange correct?
Just point it from trend micro to new exchange server and test a mail before moving the mailboxes.
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by:BAYCCS
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It sounds like changing the MX wouldn't matter b/c it sounds like Trend is just forwarding the mail to whatever.company.com and the Firewall is using NAT to forward port 25 to the server.
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jebeckham earned 300 total points
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First, you shouldn't need to worry about inbound mail being dropped during your migration.  Trend should queue things on their servers if your connection goes down and Exchange is smart enough to hande inbound e-mail during a mailbox move should something be received mid-move.

For setup on the Exchange side, I'd make sure that the receive connector on the Exchange 2007 server was setup with the "Anonymous Users" option checked on the "Permissions Group" tab.  I'd then perform some testing to make sure it could receive e-mail, including delivery to both 2003 and 2007 mailboxes in your org.  At this time, I'd also verify that it could send outbound as well and make network adjustments as necessary (for example, you maye have to allow outbound TCP port 25 from the new server at your firewall).

One you've checked things from both send and receive perspectives, I'd switch inbound mail flow so that things started coming in through the 2007 side and delivering across to the 2003 server as needed.  Next, I'd chane outbound mail flow by changing the Internet send connector on the 2007 side to start sending outbound e-mail from that side.  Lastly, I'd start the mailbox migrations to the new server.
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by:fishbowlstudios
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Thanks everyone for the responses. We went ahead and changed the firewall to accept traffic on port 25 in the new server and saw that the mail was flowing from the two servers.
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