Is it possible for a web project built on .NET framework 4.0 step into a project built on .NET framework 2? If so, how would I set this up?
These 2 projects are in different solutions. When I do a "Go to definition" from the web project, it opens up the metadata. In debug mode, the debugger never "steps into" the method.
Stepping into the project is definitely a supported scenario. The likely cause for not stepping into it is that you don't have symbols loaded in the project or you have Just My Code (JMC) enabled.
The JMC situation is the most likely. Try disabling it and retrying your scenario
Tools -> Options -> Debugger -> Just My Code
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