Prep: Preheat oven to 350°F (175°C). Peel and core the six apples.
Fill: Place a small amount of brown sugar inside the cavity of each apple and sprinkle with cinnamon. (Do not overfill).
Make Dough: In a bowl, mix flour, baking powder, and salt. Cut in the butter/shortening using a pastry blender until crumbs are the size of small peas. Add milk gradually, mixing gently until dough holds together.
Wrap: On a floured surface, roll dough into a 17x12 inch rectangle. Cut into 6 equal squares. Place an apple on each square, moisten edges with water, and pinch corners together to seal the apple inside. Place in a greased 9x13 baking dish.
Make Sauce: In a saucepan, combine 2 cups brown sugar, 2 cups water, and 1/4 tsp cinnamon. Bring to a boil and boil lightly for 5 minutes. Remove from heat and stir in 1/4 cup butter until melted.
Bake: Pour the hot sauce over the dumplings. Bake uncovered for 50-55 minutes, or until apples are tender when poked and crust is golden.
Serve: Serve warm with vanilla ice cream.