Upgrade Multiple servers from windows 2003 to 2008

Question

Hi All,
How could i upgrade all my servers (1000 around) from Windows 2003 to Windows 2008 R2 without loosing system settings, profiles and applications.
Your speedy reply is highly appreciated.

Answer 1

Since Windows Server 2008 R2 only supports 64-bit the first thing to check is that all of your 2003 boxes are running 64-bit Windows. If they are then an in-place upgrade is possible, but if they're running 32-bit Windows then there is no way to directly
upgrade them. Your only option with 32-bit Windows 2003 is to either upgrade to 2008 (which does support 32-bit), or migrate everything to a new server.
Other than that, the question then becomes what are those servers running. If they're running Microsoft services then it should be fairly straight forward, but if they're running 3rd party services then you need to check with the 3rd party company whether
their software (or more specifically the version of their software you currently have installed) supports 2008 R2.
For the Windows services there are some differences, but I believe the upgrade process handles the transition for you for the most part. Have a look at
http://technet.microsoft.com/en-us/library/ff972408(v=ws.10).aspx which details the process, and goes into the changes for each of the main Windows Server roles, and those things
you need to be aware of. As mentioned in that article, when you start the upgrade process you're offered a link to a compatibility report which will tell you if there's anything on the server which will break or cause issues with the upgrade. View that report
and review what it tells you before you start the upgrade. You may find that some tools, addons etc need to be uninstalled or upgraded before you can start the actual upgrade, but if the report gives you the green light you should be fine to continue without
any issues.
Finally, from the wording of your question I'm guessing you're wondering about getting the servers upgraded at the same time? Personally I'm not aware of any way to do that, but even if one did exist I wouldn't do it. There's too much of a chance that something
will go wrong, probably in some small minor way, but if you've just tried to upgrade all the servers at the same time, when you get reports telling you that something is no longer working you'll have a much harder time working out what caused it than if you
know that only servers a, b and c have been upgraded today, so the issue is likely to be with one of those.