In a team project I\'m working on, setting a breakpoint in a file (say IdeasController.cs) will lead to erratic debugger behaviour if there\'s another file with
I had the same problem today. I was able to trace it back to the fact that I had forgotten to set the platform target to x86 while debugging. Unfortunately the others (x64 / Any CPU) can be problematic while debugging. At least VS 2008 doesn't like them. I guess this is yet another reason to stay away.
Some speculation... I think the debugger (while running a 64 bit app) somehow "steals" breakpoints away from a file in certain cases. For me it was because another assembly was loaded first which had the same file name. I was able to avoid the issue, even in 64 bit mode, if I first manually loaded the assembly with my breakpoints: Assembly.Load("MyAssemblyWithBreakpoints");
Hope this (my first stackoverflow contribution) helps.