Save your can of pumpkin for these delicious treats. The key to achieving the perfect flavor here is roasting the pureed pumpkin in the oven first before stuffing them into that flaky pastry.
Preheat oven to 425°F. Line a 15x10x1-inch baking pan with parchment paper. Spread pumpkin evenly in pan. Roast, uncovered, for 15 minutes. Remove and cool. Reduce oven temperature to 375°F.
Meanwhile, for pastry, in a large bowl stir together flour, 2 tablespoons sugar, and salt. Cut in butter with a pastry blender until pieces are pea size. Whisk together the milk and egg. Add to flour mixture; stir just until all is moistened. Gather pastry into a ball, kneading gently until dough holds together. Divide pastry into thirds.
For filling, in a small bowl stir together cooled pumpkin, 1/2 cup sugar, 1/3 cup chocolate, and cinnamon.
Line 2 baking sheets with parchment paper. On a floured surface roll each pastry ball into a 9x8-inch rectangle. Cut into four rectangles. Brush edges with additional milk. Spoon a well-rounded tablespoon of filling onto half of each rectangle. Fold remaining half of rectangle over filling. Seal edges and prick tops with a fork. Place on prepared baking sheets. Brush with additional milk and sprinkle with additional sugar.
Bake for 20 to 25 minutes or until light brown. Remove and cool slightly on wire racks. Serve warm drizzled with melted chocolate.