Among our various servers we have a Windows 2003 Server Web Edition installation that we'd like to upgrade to Windows 2008 Web Server Edition. I've seen one post online that indicates that this is possible, but unfortunately all the official MS pages have been upgraded to refer to 2008 R2, which doesn't list much information relating from 2003 to 2008 RTM. The reason for this is that we've recently deployed DPM for our backups, however that doesn't have any support for the web editions of Windows. Ultimately we're looking at upgrading from 2003 web to 2008 RTM web, and then from there to 2008 R2 Standard, and while I know the second stage is supported, I don't know for sure about the first. Failing that we're facing either having to find an alternate backup method for that one server (which isn't very tidy), or creating a fresh install and migrating all the the websites and content to it, but neither of those (which would take ages since there are a lot of websites on that server and some of those we don't directly manage / maintain). Can anyone confirm if that upgrade is possible?

Windows 2003 Web edition does not have a upgrade path http://technet.microsoft.com/en-us/library/cc755199(WS.10).aspx#BKMK_Supported

Upgrades to Windows Server 2008 R2 from the following operating systems are not supported: Windows® 95, Windows 98, Windows Millennium Edition, Windows XP, Windows Vista®, Windows Vista Starter, or Windows 7 Windows NT® Server 4.0, Windows 2000 Server, Windows Server 2003 RTM, Windows Server 2003 with SP1, Windows Server 2003 Web, Windows Server 2008 R2 M3, or Windows Server 2008 R2 Beta For more information. Use IIS forum for web site migrations. Thanks.

Hi, The Windows Server 2003 Web Edition operating systems cannot be upgraded to Windows Server 2008, you must perform a clean install and migrate the data from the computers to the new operating system. For more information, you can refer to the Upgrade limitations section of the link provided by dariusg. Thanks. NinaPlease remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

Thanks for the comments everyone. Of course it's also since dawned on me that even if I could upgrade 2003 web edition to 2008 RTM web edition that wouldn't help, since they'd both be 32-bit, 2008 R2 is 64-bit only, and you can't upgrade from 32-bit to 64-bit. Guess it'll be a clean install then!