Upgrade Exchange Server 2007 SP2 Running on Server 2003 R2 x64 to Server 2008 x64


I have a grand idea that I am hoping will work out.  I would like to upgrade the OS of our current Exchange Server from Server 2003 R2 x64 to Server 2008 x64.  We are currently running Exchange Server 2007 SP2 on the 2003 machine.  I would like to upgrade the OS as I mentioned, and then, I would like to update to Exchange Server 2007 SP3.  That would then open the door to the possibility of us again upgrading the OS to Server 2008 R2.

I have successfully in-place upgraded a copy of our Exchange VHD from Server 2003 x64 to Server 2008 x64.  I haven't yet tried to test run an SP3 update to the Exchange Server.  I am doing this, of course, not connected to the network as it would break our email.

My question is am I trying to do something that is possible?  I am going to have to do this over a weekend when our email can be offline for hours at a time.  I don't want to attempt this if it is not possible.  Again, we have our Exchange Server running on a VHD, so rolling back is always an easy option to do.  Please advise.

Thanks in advance!
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Cliff GaliherCommented:
Doing an in-place upgrade of the OS while exchange is installed is not supported. I wouldn't do it at all; I've seen people ignore the "not supported" warning and break their environment badly. Not worth the risk. Always better to migrate.

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Nick RhodeIT DirectorCommented:
Wouldn't try it in my opinion.  What I would do is build another server with 2008 R2, install exchange and update it to sp3, then migrate everything over.
As if it weren't enough from 2 experts, I'll be the third!

I would advise very very strongly against this.  As the previous experts said, you should install a fresh exchange install on top of the new 2008 install instead of the upgrade path.
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Simon Butler (Sembee)ConsultantCommented:
"Again, we have our Exchange Server running on a VHD, so rolling back is always an easy option to do."

No, it isn't.
You roll back something like this and you will break Exchange. Exchange is a living product, everything changes. Rolling back to a previous "snapshot" or whatever will usually break Exchange.

Therefore as well as the advice above about this being a bad idea, your fall back is also a bad idea.

Build a new system and move the mailboxes. Zero risk, zero downtime.

I'll be number 4...Don't do this.

Build a new system...new installed OS, and new installed and updated Exchange (move up to Exchange 2010 or 2013...if you get too far behind the migration gets harder) and migrate.

If you are going through the trouble and time to build new servers (even on VHDs) you should put in a more current Exchange to save yourself migration headaches in the future.
Meanwhile upgrading just Exchange 2007 from SP2 to SP3 is nothing... there is no reason why you shouldn't have Ex2k7 sp3 RU11 aka 8.3.0327.01... just keep Windows Server 2003sp3 although I can understand you probably want a better VM compatible OS like 2008R2 so you could use virtual memory and stuff.

everyone here is complaining about your Windows upgrade from 2003 to 2008R2... which you've apparently already done in a test environment with a copy of the main VM, but it probably wouldn't be much more difficult to create VM with new OS and install Exchange then transfer the mailboxes -- BEST and SUGGESTED option... although I would upgraded all the Exchanges to the same version aka the latest build before I did the move and so wouldn't use SP2...

As a sidenote, I wouldn't even do what you are suggesting, but if I did go that route I would have upgraded Exchange first then have upgraded the OS rather than doing it the other way around...  Exchange 2007SP2 to Exchange 2007SP3 is fine and good and minor and not as drastic as the unsupported non-recommended Windows 2003 to Windows 2008R2 so I would have done the Exchange first.
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