When I add a breakpoint and hit F5 to run in the debugger (I am using my debug build), a dialog pops up telling my my web.config file does not have debug=true in it (which is does) and I get 2 choices a) run without the debugger or b) let visual studio update my web.config file. If I choose b) the web.config is updated badly and nothing will work. If I choose a) then the site appears and I can test it out, but no debugging.
I am an experienced developer, but I have never used visual studio and asp.net for web development before, so I am feeling rather frustrated by all the walls it is putting up to prevent me working.
So far I have not been able to use the debugger. Is there something totally obvious that I am missing? What would you check if it was happening to you?
Open web.config manually and make sure the following line is in there
Now you should be able to debug from VS. If this does not work I suggest that you recreate the project.
EDIT: perhaps from what you say it could be that web.config is screwed up, e.g.contains invalid xml, no closing tag for some element etc.