Preheat the oven to 325 degrees. Line muffin tins with 24 cupcake liners.
Beat the cake mix, pudding mix, oil, milk, and eggs for 2 minutes. Spoon batter into the prepared muffin tins. Bake for 18-20 minutes, or until the tops spring back. Cool on a wire rack.
In a small bowl, whisk the milk and pudding mix until creamy and thick. Beat the cream cheese until creamy. Add the pudding and beat again. Fold in the whipped topping.
Use a cupcake corer or small knife to cut out the center of the cupcakes. Spoon the cheesecake filling into a piping bag with icing tip 12 and fill the centers. Refrigerate while you make the frosting.
Beat the shortening and butter until creamy. Add the salt, vanilla, and strawberry extract and beat again. Slowly add half the powdered sugar until it is mixed in.
Place the water and strawberries in a food processor or blender and puree. Pour into the frosting and beat until creamy. Add the rest of the powdered sugar and beat until light and fluffy. Use a large piping bag and icing tip 1M to swirl the frosting on the chilled cupcakes. Add the cookie sticks and a fresh berry to the top of each cupcake. Refrigerate cupcakes until time to serve. Makes 24 cupcakes.