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Do I need to run adprep from server the 2003 R2 media before I can run adprep32 for Server 2008 R2? Or can I go straight from 2003 schema -> 2008 R2 schema?

Do the adprep executables include all the previous versions of the schema and update accordingly?

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Yes, using the latest adprep will upgrade correctly. From Running Adprep.exe on TechNet:

Adprep.exe is a rollup of all previous versions of this tool. In other words, if you currently have domain controllers that run Windows Server 2003 and you want to add domain controllers that run Windows Server 2008 R2, you only have to run Adprep.exe from the Windows Server 2008 R2 operating system disk. It is not necessary to run the version from Windows Server 2008 because the version in Windows Server 2008 R2 includes all the changes from previous versions.

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That's what I assumed, but I wanted to check. Thanks! –  mwheeler1982 May 10 '12 at 16:22
    
As a tidbit of good info... trying to go right from 2K to 2008R2 will result in some nice bluescreens :) –  SpacemanSpiff May 10 '12 at 16:24
    
@SpacemanSpiff I would hope updating the AD schema wouldn't be the source of the BSOD. –  jscott May 10 '12 at 16:25
    
I reproduced it using VMs literally you hit enter on ADPREP32 and BAM all the 2K boxes BSOD. I know step people to 2003 first to avoid the condition. –  SpacemanSpiff May 10 '12 at 18:28
    
@SpacemanSpiff Wow, thanks for that. I will note this for [potential] future usage. Pretty interesting. –  jscott May 10 '12 at 18:29

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