Exchange 2007 after Windows 2008 Upgrade

I know it has been well documented that you cannot upgrade Windows 2003 to Windows 2008 with Exchange 2007 installed and expect Exchange 2007 to keep functioning.  However, let’s say you may have accidentally done the upgrade on a standalone Exchange 2007 box you have, you know, just in case it were to happen (like it did to me).

Prior to doing the upgrade, you’ll notice a few things.  First of all, you’ll be prompted that you need to uninstall Powershell.  However, no where does the compatibility checker say anything about needing to uninstall Exchange 2007 prior to upgrading.  I found this hilarious (in a sad, pissed off way) because I had tried to upgrade my WSUS virtual machine first, and it had told me that I would need to uninstall Powershell and WSUS prior to upgrading.  I’m so glad that I wasn’t told anything about Exchange in a similar fashion.  Ugh.  By the way, I was running Exchange 2007 with SP1 prior to the upgrade…of death!

The first stumbling block, which should have caused me to stop the upgrade process, was uninstalling Powershell.  Since I had installed it prior to installing SP2, uninstalling it becomes a pain.  This is because Powershell is a windows update and if you install a service pack you can’t uninstall any updates prior to the service pack.  Lovely.  Well, in another unsupported way you can uninstall it.  You have to browse to %windir%$ntuninstallkb926139$spuninstall and run the spuninstall.exe.  Now, this may or may not be on your machine anymore either.  On some of my virtual machines it was there, but on my Exchange server it was not, so I copied it over and ran it.

Ok, so now I can upgrade, yay!  Windows does its thing and upgrades everything and restarts successfully.  I was actually fairly impressed when it booted up.  It looked like it actually worked.  However, then I went into the services snap-in.  I usually do this with this machine because it is slightly RAM starved and sometimes all the Exchange services don’t start.  Sure enough, they hadn’t all started.  So I went through and tried to start them all.  All started but the information store and the system attendant service because of a dependent service.  Crap, of course it’s the important ones.

Well, first thing I tried was to reinstall Exchange 2007 SP1, just to see if that would work.  Of course this required me to reinstall Powershell, since that’s a pre-req.  No big deal, installed that easily.  Then when I tried to actually install SP1 it just bombed saying it couldn’t upgrade.  Looking through the eventlogs it was because it was trying to spin up those two services.  Great.

Well, doing some quick registry editing, I found that the service it was dependent on was NtlmSsp.  Needless to say, this service does not exist on Windows 2008, hence the issue.  Two seconds later, I removed that dependency from within the registry and restarted the machine.  The machine reboots, and low and behold all of the services start.  And all the email that was in the queue on my Edge Transport machine left the queue and made it into Exchange.  Downside is that I was doing this all remotely and OWA still didn’t work.

Honestly, I wasn’t that worried about OWA.  I mean, as long as I can get my emails back and then do the correct upgrade (aka, no upgrade at all) I’d be a happy camper.  Heck, even after installing Powershell back on it, I was able to open up Exchange System Manager.  Really, if I didn’t know all about the services and didn’t use OWA, I would’ve never known it wasn’t working.  Oh, well, maybe the exceedingly high CPU utilization, but oh well.

When I got home, I had to test to see if I would be able to access my email.  Sure enough, Outlook worked like a charm.  I received all the queued email that had been sitting there for a day, and I was even able to send an email.  Pure craziness. 

What makes this even better is that the Exchange team actually decided (well, they actually went into it knowing what they were getting into) to try this same thing too.  However, they weren’t able to get things working.  I think the large mess-up was re-installing SP1.  I’m glad I didn’t decide to go down that path, especially since mine worked.  Needless to say I’m working on building a new VM with Windows 2008 and then going to add it t the ORG and move the mailboxes over to the new one.  However, in the meantime, at least my email is functioning 🙂

I’ll be sure to post again on if I ran into any more issues with the mailbox move.  Worst case I suppose I could just do an ExMerge (actually Export-Mailbox for 2007) on the mailboxes or dump the email out of outlook to a PST.  I’d rather not do that, but if that’s what it takes…