Sift together 2 tablespoons sugar, the baking powder, salt and flour. Cut in shortening and stir in 1/4 cup milk. On a floured board, roll out the dough to about 1 1/2 inch thickness. Cut dough into 6 squares.
Peel and cut apples in half and core them. Put 1/2 apple onto each piece of dough. Put 1 teaspoon sugar onto each apple. Pull up the corners of each dough square and close them together; press to seal well.
Tie each dumpling into a piece of cheesecloth or muslin. Drop dumplings into a large pot of boiling water. Cook about 25 minutes. Serve with milk, sugar and cinnamon.