In a small bowl, combine sugar and cinnamon. Coat one side of each tortilla with nonstick cooking spray; sprinkle with cinnamon sugar. Turn tortillas over; repeat on the other side.
Cut each tortilla into four wedges. For each dessert cup, place round edge of one tortilla wedge in the bottom of a muffin cup, shaping sides to fit cup. Place a second tortilla wedge in muffin cup allowing bottom and sides to overlap.
Bake at 350 F for 10 minutes or until crisp and lightly browned. Cool completely in pan.
Meanwhile for filling, beat cream cheese in a mixing bowl until smooth. In another mixing bowl, beat milk and pudding mix on low speed for 2 minutes. Beat in cream cheese on low until smooth. Fold in whipped topping. Cover and refrigerate for 1 hour.
Carefully remove cups from pan. Pipe or spoon about 3 tbsp. of filling into each cup. Drizzle or pipe with melted chocolate. Refrigerate for 5 minutes or until chocolate is set. Store in the refrigerator.
Adapted from My friend, Stephanie B.