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What to expect during an exchange migration

Posted on 2014-02-19
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Last Modified: 2014-03-05
I am going to be migrating from exchange 2007 which is running on an SBS 2008 box to Exchange 2010 which will be running on a Windows 2008 R2 box. The process is pretty straight forward. However, I do have a few questions:

Some of the guides I've read are instructing me to change my firewall to direct port 25 traffic to the new exchange 2010 server BEFORE I've even moved any mailboxes. Is that right? Why would I try to deliver 25 traffic to my new server before any mailboxes are moved to it - or is exchange 2010 smart enough to know that the mailboxes still reside on the sbs 2008 server?

I'm concerned about what happens after I move a mailbox. First, when that user launches outlook for the first time, what happens? Is outlook/exchange smart enough to see that the mailbox has moved to the new server and outlook automatically points to the new server? Also, what happens to mobile devices like phones, once I move a mailbox? Will that break their mobile phone until I point OWA traffic to the new server? What happens if I were to point 443 traffic to the new server BEFORE I started moving mailboxes (same thinking as changing port 25 traffic before I start moving mailboxes).
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Question by:StarfishTech
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ktaczala earned 500 total points
ID: 39871619
During a migration the installer will create a routing group connector between the 2 exchanges,  changing port 25 to the new exchange is correct, it will forward the mail onto the old exchange server automatically.

you can move mailboxes to the new exchange at any time.  The next time the user opens outlook it should point to the new exchange server (barring any mis-configuration issues).

Owa will not work until the mailbox is moved to the new server.

Smart phones will need to be manually changed from "mail.mydomain.com/exchange" to "mail.mydomain.com/owa
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by:StarfishTech
ID: 39871667
Thanks for the information. What is we were to point port 25 to the new server BUT leave OWA pointing to the old server. Would that atleast ensure that the mobile devices work UNTIL the mailbox is moved to the new server? However, that also poses the question - will Outlook anywhere be broken for mailboxes moved to the new server if my firewall is still pointing 443 traffic to the old server? Ugh, the mobile devices are nothing but a pain in the ass when it comes to migrations.
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by:ktaczala
ID: 39871743
Yes, owa and outlook anywhere should function as normal until the mailbox is moved.

I usually do this over a weekend, less immediate impact.
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by:StarfishTech
ID: 39871778
So this is my dilemma. They want me to move all the remote users using Outlook Anywhere on Friday evening. Then, they want me to move all users with mobile devices on Saturday night. They want the Outlook Anywhere users to be working first thing Saturday morning. They want Mobile devices to work until we move the mobile device users on Saturday evening. I think I'm screwed. Am I right in assuming that there will be no way to have mobile devices working for mailboxes still on the old server AND Outlook Anywhere working for mailboxes already moved to the new server? If I leave OWA pointing to the old server, what happens when I move the mailboxes to the new server? Mobile Device AND Outlook Anywhere would break?
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by:ktaczala
ID: 39871933
Outlook anywhere doesn't use the /owa or /exchange, just the mail.servername.com so as the minute you move the port 443 to the new server all outlook anywhere and mobile devices will shift to new server.
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by:StarfishTech
ID: 39871956
Ok...I get that. But do you see my dilemma? They want us to move the outlook anywhere users  mailboxes Friday night and have outlook anywhere working Saturday morning ANd have mobile devices working all Saturday for the mailboxes that aren't going to be moved until Saturday night. Is that even possible? Outlook anywhere and the mobile devices both communicate on port 443 so I can't have 443 pointing to both servers......

In that instance, would I need two public ips....one for outlook anywhere users that have been moved to the new server and a different public ip for the mobile device users that still reside on the old server?
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by:ktaczala
ID: 39871984
No, that won't work unless you create another CNAME record so https://mail.mydomain.com/exchange points to old IP, and https://newmail.mydomain.com/owa points to new IP

I would assume your current config is something like this:
'mydomain.com' points to your static IP
'mail' points to mydomain.com (CName Record)
'@' points to mydomain.com (MX Record)
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by:StarfishTech
ID: 39872052
im going from 2007 to 2010 so both are /owa. so could i just do something like "oldexchange.company.com points to old exchange server and newexchange.company.com points to the new server?
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by:ktaczala
ID: 39872065
yes, but like you asked you will need 2 IP's
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by:StarfishTech
ID: 39872121
thanks. I guess i'm still a little confused as to when the best time would be to change 443 to point to the new server if I just decide to use the existing (1) static IP. If I leave 443 to point to the old server and move a mailbox to the new server, would Outlook Anywhere users automatically redirect to the new mail server? And from what you tell me, If I leave 443 pointing to the old server and move a mailbox with a phone, the old server is not smart enough to redirect that activesync request to the new server and vice versa?
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by:ktaczala
ID: 39872166
What you suggest should work, keep 443 pointing to the old server, and move an outlook anywhere mailbox user over to the new exchange,  traffic should still flow.

To test it I would create a test user for Outlook anywhere move the mailbox and try send & receive.  Same thing with web mail.  Moving the mailboxes shouldn't break flow.
Only when you redirect port 443 will things need to be changed.
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