This post is meant as a warning for anyone out there thinking about upgrading Microsoft Exchange Server and the new hoops you must jump through. Up to and including Exchange 2000 to Exchange 2003 an in place upgrade has been supported for Exchange, however this has changed since that time. Now just about anytime a new version of Exchange or Windows Server comes out you have to do a migration upgrade which requires at a minimum two servers (at least temporarily) which if you are a small shop with only one exchange server or even one server (hello SBS users) is a bit of a challenge. I wanted to outline the versions and supported upgrade paths so people can now what the possibilities are and ways to skip some migrations.
Exchange 2000 / Windows Server 2000 32-bit – Fall 2000
In Place Upgrade to
Exchange 2000 / Windows Server 2003 32-bit – Spring 2003
In Place Upgrade to
Exchange 2003 / Windows Server 2003 32-bit – Fall 2003
Migration Upgrade required due to Ex2003->2007 and 32-bit->64 bit
Exchange 2007 / Windows Server 2003 64-bit – Fall 2006
Migration Upgrade required due to IIS6->IIS7 and Powershell
Exchange 2007 / Windows Server 2008 64-bit – Spring 2008
Migration Upgrade required due to Ex2007->Ex2010
Exchange 2010 / Windows Server 2008 64-bit – Fall 2009
Possibly In Place Upgrade to
Exchange 2010 / Windows Server 2008 R2 64-bit – Fall 2009
The last two will most likely be merged and I would recommend just waiting for both Exchange 2010 and Windows Server 2008 R2 to do the upgrade. They are both supposed to be released in the Fall of 2009 and doing them together since another server will be required will be easier than separately. Gone are the easy old days of Exchange upgrades now it seems you will always need extra servers.

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