Web server upgraded to Windows Server 2008
We just finished upgrading this web server to Windows Server 2008 from Windows Server 2003, which was a major PITA. The entire DMZ is virtualized (including the domain controllers) and the upgrade resulted in the corruption of AD, so the entire forest had to be rebuilt from scratch. The virtual drives of the web servers were too small to process the upgrade, so they had to be expanded as well. With Windows 2000 and Windows 2003 a 16GB expandable drive is more than enough for a web server, even after adding an \I386 folder for the CD and service packs. However, with smallest full install of Windows Server 2008 requires about 7.5GB and at least that much space to perform an upgrade from Windows Server 2003.
This site has been up and down over the past 4 days during the upgrade process. After 3 days, we finally had the new forest up and a viable version of the web servers running in 80GB expandable virtual drives. It then took almost 8 hours for the server to upgrade to Windows Server 2008 and another 4 hours to get all the applications working, mostly due to issues caused by the expanding of the virtual drives. A long story short, we're up and running again. We had to upgrade the servers for a new site that is written to run on IIS7 and is going on-line within the next 2 weeks. We'll make another announcement once the new site goes on-line.