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    You can debug Application_Start by either starting the web app from within Visual Studio by setting it as the startup project, or by putting Debugger.Break() inside Application_Start and then attaching when it hits the debug dialog. Commented Sep 26, 2009 at 22:39
  • Both are not options since I don't have the source code. I'll try windbg. Can I then use VS to debug a process that windbg is attached to? If not, how useful is windbg in debugging a managed assembly (local variable watch, call stack, etc)? Commented Sep 26, 2009 at 23:09
  • Windbg is one of the most powerful debugging tools available - more powerful than VS's debugger. Unfortunately, it's also it's own environment which can be fairly cryptic and has a steep learning curve (IMO). You can use the SOS plugin to debug managed code very effectively though - I would suggest following the first few tutorials on the site that I linked, they'll get you started pretty well. Commented Sep 26, 2009 at 23:59