Debugging No Touch Deployment apps
So you've built a WinForms app and its a struggle to deploy, here are some tips.
Clear the IE and download cache (gacutil /cdl) on the client machine to ensure that old versions of dll's have not been left lying around.
Check the client machine trust's your application/website.
Ensure the vitrual directory (in IIS) that has your .exe and .dll's is properly configured
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Ensure the permissions are set to Read and Run Scripts. (Not Execute as that would try to run applications server side).
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If the application uses a configuration file then ISS's default handling must be disabled: Under Configuration dialog in the Mappings Tab, remove the entry for the .config extension.
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Don't use a virtual directory named “exe“ - apparently asp.net has a directory watcher process that 'corrects' the permissions of exe directories once a day.
Use your IIS log to see if the application files have been sent to the client.
Enable the "IEHost Log" (more details including how read the log at: 
http://support.microsoft.com/default.aspx?scid=kb;en-us;313892)
Add the following registry keys (using Regedit):
In HKEY_LOCAL_MACHINE/Software/Microsoft/.NETFramework
- Add a DWORD value named DebugIEHost to this key; assign it any non-zero value.
- Add a string value named IEHostLogFile. Assign it the full path (including the file name) of the file in which you want to record the debug trace (for example, C:/Temp/IEDebug.log).
Use fuslogvw (installed with dev environment) to look for binding errors. At the end of the help page there are a couple configuration settings that are occasionally useful in debuginng bind problems.
Now the application is running on the client machine here are the tools I use to debug it:
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To launch a debugger, put the call 'System.Diagnostics.Debugger.Break();' in your code. That will launch the JIT debugging dialog. I recommend you choose 'New Instance of Mircosoft CLR Debugger 2003' (don't choose your current editing devenv, it will probably lock up).
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Attach to the running process via the Processes dialog (Debug -> Processes...)
- To capture Debug.WriteLine() output, use Sysinternals DebgugView This is the only option that doesn't require the development enviroment on the client machine.
If you want to see a no touch deployment application in action, see my posting: First Commercial .NET No Touch Deployment application