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Created attachment 367 [details]
screenshot of debugging watch context menu
I'm not sure if it's related to generics or not, however this simple test case produces the issue. Put breakpoint at end of code and hover over the "twodimension" variable. The first level expansion turns black with the mouse over and expands when clicked, however the second level doesn't seem to detect the mouse over it as it doesn't turn black and additionally when clicked collapses the context menu and leaves it in an unexpected state (it's seems selected but doesn't interact with mouse anymore). The screenshot below, although not too useful, was taken with the mouse hovering over the select level triangle (should be black).
public static void Main (string args)
List<List<string>> twodimension = new List<List<string>>();
List<string> firstDimension = new List<string>();
twodimension.Add( firstDimension );
Doesn't seem to happen with current versions of Xamarin Studio.