For now Grome is using ray picking to generate the shadow. The generated shadow is pretty simple in the sense that it is not using complex lighting and shadowing algorithms (global illumination, penumbra generation). And, yes, it is not using the alpha from the objects to detect the actual object visible shape.
In the future we will make more complex shadowing algorithms but I cannot give you a certain date (and I bet we will tend to implement a dynamic implementation using shadow maps than a static baked texture).
The solution is not simple enough to be easily implemented (the shadow techniques are a vast domain). The best solution for you, for now, is to generate the terrain shadow in different modeling application that supports more complex lighting models (like 3DS Max 9 for which you can import the geometry as COLLADA and generate the shadowmap on the planar mapping of the terrain).
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