Heat oven to 350. Make and bake cupcakes as directed on box, adding all ingredients suggested on box and adding almond extract, if desired. Cool in pans 10 minutes; remove from pans to cooling racks. Cool completely; about 30 minutes.
Just before serving, remove paper baking cups. Cut cupcake in half horizonally with serrated knife. On bottom half of cupcake, spoon 1 tablespoon cherry pie filling; top with 2 teaspoons vanilla pudding. Replace top of cupcake.
Remove lid and foil cover from frosting container. Microwave frosting on High 30 seconds. Stir thoroughly until very soft and smooth, microwaving an additional 5 to 15 seconds if necessary. Spoon 1 tablespoon frosting over top of cupcake. Top with cherry from pie filling. OR, you could use a stemmed maraschino cherry in place of the pie filling cherry.
Repeat steps 2 and 3 with remaining cupcakes. Serve immediately.