Upgrading to Server 2008 onto Boot Drive that is too small

Lojikbom

Solid State Member
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I have a server running Windows Server 2003 in RAID5 configuration and would like to upgrade to Server 2008. Whoever installed 2003 on it only dedicated 9GB to the boot partition. The remaining 600GB+ is dedicated to the data partition. Server 2008 needs a minimum of 10GB to install. Server 2008 also comes with partition resizing capability whereas Server 2003 does not.

Is it possible for Server 2008 to resize the boot partition to an optimal size (e.g., 40GB+) during the upgrade? Or am I screwed and have to backup all the multi-hundred GBs of data on the server and perform a clean install?
 
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