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I'm experimenting with the AppDomain's 'AssemblyResolve' event by hidding the depedencies for an executable file in another folder. The assemblies seem to beloading and executing fine, however debugging seems to be crazy, sometimes it hits my break points, sometimes it doesnt , and sometimes it hits the same code twice(It seems absurd but I'm sure the code is executing only once). I don't understanding how debuggers works but I guess it has something to do with the PDB files. Anyone got an idea of what might be happening and how can I fix it?

Edit: Let me add that I'm calling methods on the dynamically loaded assemblies using reflection, sometimes the method I'm stepping over throws an exception that only pops at a later time.

+1  A: 

Debug + Windows + Modules, find your DLL in the list. Right-click it and choose "Symbol Load Information". It will show you where it found the .pdb file.

Finding the wrong .pdb is not a great explanation for your troubles btw. Maybe you ought to post to connect.microsoft.com. Giving them a good repro would be essential however.

Hans Passant