Preheat the oven to 350 degrees F (175 degrees C). Place 1 cup of sugar and 2 cups water into a saucepan and bring to a boil.
In a medium bowl, cream together the shortening and 1/2 cup sugar until smooth. Combine the flour, cocoa, baking powder and salt; stir into the creamed mixture alternately with the milk so the batter does not become too stiff. Stir in vanilla.
Pour the sugar water into a 2 quart casserole dish. Drop the chocolate mixture by spoonfuls into the sugar syrup to make dumplings.
Bake for 45 to 50 minutes in the preheated oven. Use a slotted spoon to remove dumplings to plates, spoon syrup over and serve.