In the end, it appeared this was a combination of bloated csproj files, coupled with instability in Visual Studio 2013.
If you are using Visual Studio 2013, I highly recommend installing Update 2. It appears to make tasks a lot more reliable.
I never figured out what governs the Managed setting, however I have found the following option:
- Click Attach to Process
- Underneath Transport/Qualifier/Transport Information, there is a box marked Attach To:
- By default, it is set to perform Automatic selection.
- Click the Select button.
- Toggle from Automatic to "Debug these code types"
- Tick one or the other (not both) of the entries for "Managed ([.NET version])"
- Click OK
I have had some success in getting the Debugger to attach properly to the IIS Express processes that are running Managed debuggable code that it "automatically" doesn't let me (for seemingly random reasons).