Unable to start debugging on the Web server

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Here is a complete troubleshooting page from MDSN:

http://msdn.microsoft.com/library/default.asp?url=/library/en-us/dv_vstechart/html/vsdebug.asp


If you use the framework 1.1 , you may have to reinstall asp.net:
C:\WINDOWS\Microsoft.NET\Framework\v1.1.4322\aspnet_regiis -i

If the probleme persist, you may have to reinstall Visual Studio, or even the framework...