For complex symbols, there is somtimes a difference between the symbol that ArcGIS Server draws in the server-side created legend, and the (sometime simplified) symbol representation that it reports on the REST Service directory (which I'm guessing is what Robert's widget is using).
This symbol mismatch is also true for certain complex symbols if you compare how they look in the Edit Widget (using the REST symbol) and the Legend widget (created server-side). We are working on ways to make that better for 3.0 and ArcGIS 10.1.
I'm guessing this might be same issue causing problems for Ashley.