To whom it may concern :

I have a virtualized Windows 2003 Web Edition (x86) that needs to be upgrade to Windows Server 2008 (x86).  It has several web applications installed and configured thus clean install of Windows Server 2008 is not an option.

In short, I get a "Upgrade has been disabled" message. 
It also says, "You cannot upgrade from Windows Server 2003 Web Edition to Windows Web Server 2008.  You can upgrade to ."  Would you please help?

FYI. the Windows Server 2003 has a single partition and setupact.log as follow:

2015-03-21 23:08:20, Info       [0x0a000a] UI     Autorun:Autorun core successfully  initialized!!!
2015-03-21 23:08:20, Info       [0x0a000b] UI     Autorun:Autorun UI successfully  initialized!!!
2015-03-21 23:08:21, Info                  UI     AppWindow has layout style 0
2015-03-21 23:08:21, Info                  UI     NavWindow has layout style 0
2015-03-21 23:08:21, Info                  UI     NavWindow has layout style 0
2015-03-21 23:08:22, Info                  UI     Page with ID 2018 returned 0 for CanPageBeActivated with choice 0
2015-03-21 23:08:22, Info                  UI     Page with ID 2002 returned 0 for CanPageBeActivated with choice 0
2015-03-21 23:08:22, Info                  UI     Page with ID 1200 returned 1 for CanPageBeActivated with choice 0
2015-03-21 23:08:22, Info                  UI     Page with ID 1200 returned 1 for CanPageBeActivated with choice 0
2015-03-21 23:08:22, Info       [0x0a011c] UI     WizardDialogPost::SetActive
2015-03-21 23:08:26, Warning    [0x0a0010] UI     WM_KEYUP for 9 key on 0
2015-03-21 23:08:26, Warning    [0x0a0010] UI     WM_KEYUP for 16 key on 0
2015-03-21 23:08:26, Warning    [0x0a0010] UI     WM_KEYUP for 16 key on 0
2015-03-21 23:08:26, Warning    [0x0a0010] UI     WM_KEYUP for 17 key on 0
2015-03-21 23:08:26, Warning    [0x0a0010] UI     WM_KEYUP for 17 key on 0
2015-03-21 23:08:26, Info       [0x0a018e] UI     Passing command line parameter ("D:\Sources\setup.exe /HideWelcome /uilanguage:en-US /targetlanguage:en-US") to IBS.
2015-03-21 23:15:51, Info       [0x0a013b] UI     Cancel rejected. Remaining on Page Install Windows.

Looks like you'll need to clean install it.

From the following versions of Windows Server 2003, there are no supported upgrades:Windows Server 2003 Web Server Edition SP2 and Windows Server 2003 Web Server SP1

https://support.microsoft.com/en-us/kb/951041

 These ones may help.

http://blogs.iis.net/bills/archive/2008/06/18/how-to-migrate-from-iis-6-to-iis-7.aspx

http://www.iis.net/downloads/microsoft/web-deploy

Also might ask over here.

http://forums.iis.net/

http://forums.asp.net/

Hi,

Any update about the issue?

I would agree with Dave, 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.

Regards.