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Exchange 2007 Single Server Migrations for Profit or Headache

I was originally writing up a guide for migrating, actually transitioning, Exchange 2003 to Exchange 2007. There are lots of guides out there that would have better screenshots and perhaps even better written steps. Basically I would not really be meeting a need as there are already plenty out there doing so. So instead I am scrapping all of my original work and concentrating on issues that I believe are not talked about as much out there. Mostly these issues affect those that are doing single server migrations, which is basically you have one Exchange 2007 server holding all of your roles. They have caused me a great deal of headache and drama which I am sure is true for others doing such migrations as well. I would imagine that this is mostly the SMB sector, which is where the majority of my work in this is being done. Let’s talk about the biggest issue now, client access.

The CAS role plays a big part in your Exchange organization as it is the broker for all requests to your mailboxes. You will have MAPI requests as well as HTTPS, POP3 and others coming into this server. By the way as a security side note the recommended set up is to have your CAS role on your internal network with a reverse proxy in your DMZ for proxying requests through to your CAS. The CAS when it receives a request for a mailbox that resides on a 2003 servers proxies that request through to your 2003 server. No issues at all there. The problem that comes up, though, with having a CAS on the same server as your MB is that web requests no longer get proxied to your 2003 servers, they get redirected. This is due to davex.dll handling the requests on a mailbox server, and it will grab the requests first. Exprox.dll is what handles proxying. This redirection is not configurable either. So that causes a problem when it is redirecting an external request to an internal FQDN. That doesn’t work out too well and you get lots of angry OWA users wondering why their logins take them to an invalid address. For a more in depth explanation take a look here. Let’s take a look at a few ideas for mitigating this issue.

First off an easy fix would be to make sure your Exchange 2003 FQDN has a matching public address. This is not a recommended set up though at all. It is against best practices to have your internal domain match your external domain. Not to mention you can get a number of funny DNS issues going on if this is the case unless you’ve planned things out well. Read this article for some more DNS information, and especially look at the split-brain section. All of this can turn your easy fix into a much more complicated fix. If the stars do just happen to be right on your migration though, then go for this. Set up a public record matching your internal Exchange 2003 name and you’ll be set. This will be transparent to your users.

Next up would be to use a reverse proxy such as ISA 2006. This would be great as it keeps the strict definitions of your DMZ as it keeps your Exchange servers from having to blur the lines. This doesn’t seem to be something that most SMBs care about in my experience though. They don’t seem to see the need for security and how having a properly defined DMZ fits into this. But that goes into an entirely separate article and could sound a bit ranty.

Other methods will require a bit more cooperation from your users. Remember, in Exchange 2007 the OWA access by default is /owa. So you will need to communicate this to your users as you migrate their mailboxes over. Then, remove the /exchange virtual directory through the Exchange Shell and recreate it in IIS. Finally, set up /exchange with a custom 403 redirect to a different port on your external address. Mind you that you’ll need to make sure that port does point to your legacy server. This either requires your firewall to be able to do port translation or changing the ports on your 2003 server.

Finally, and the most recommended method, is to set up a temporary virtual machine that will purely host a CAS role. Then everything will be proxied as it is supposed to be. The down side to this is that it would require a separate license in which case you might as well plan for as separate CAS to begin with.

Fortunately as long as everything is configured properly Outlook Anywhere and ActiveSync seem to work just fine. Some dangers with those is if you are having some DNS issues internally or improper communication with a global catalog. This can add to your headache so you will want to cozy up to rcpping which you can grab from Microsoft and get more info about how to work it from here. Another great site I have recently found out about is the Remote Connectivity Analyzer. This site will enable you to test Outlook Anywhere, ActiveSync, SMTP and Autodiscover with detailed error messages about where these break down. It will become your best friend very swiftly.

I guess the moral of all these suggestions is to make sure you have your migration well planned out. Run it through a test lab first if you are able. Definitely make sure you test it out, and definitely don’t spring it on your users unawares. You could be in for quite a “fun” surprise.


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