well, you’d think that upgrading windows server to the next release wouldn’t be too much trouble. the windows 2008 upgrade install just happens to have a problem with powershell being installed though.

and most likely everyone has applied service packs or windows updates to 2003 so that powershell has snuck onto the system some way or another. the problem is there is no add/remove programs entry for powershell…and microsoft’s kb article that lists hot fixes that install powershell weren’t listed (at least for me). so…i decided to just remove SP2 entirely. this step seemed to get me closer to success, but instead of the compatibility report listing powershell as a problem it now just showed up blank.

turns out you need to uninstall “windows management framework core” and then proceed with the upgrade. the compatibility report will still show up blank, but now you can at least click Next to proceed with the upgrade install.

found the solution in the comments on this blog (not in the actual blog entry itself):
http://blogs.msdn.com/b/powershell/archive/2007/03/19/windows-server-2003-sp2-upgrade.aspx

quick update 9/18/2014:
show updates must be enabled for “windows management framework core” to be visible in add/remove programs

update 5/7/2015:
encountered an instance where i could not get powershell to uninstall cleanly and thus was prevented from starting the 2008 upgrade. the technique of renaming c:\windows\system32\windowspowershell to something else worked for me.
source: http://williamfaulkner.co.uk/2013/02/server-2003-to-server-2008-upgrade-powershell-compatibility-error/

plus…if you have old hardware drivers on a system (on a P2V for example) they’ll need to be removed. i removed the “afamgt.sys” file as mentioned in this article for dell hardware drivers: https://support.microsoft.com/en-us/kb/941024

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