1. Spray a cupcake pan with non stick cooking spray. Preheat oven to 350°F (176°C).
2. To make the cookie dough, cream the butter and sugar together for 3-4 minutes, until light and fluffy.
3. Add the egg and coconut extract and beat until well combined.
4. Add the dry ingredients to the wet ingredients and mix until smooth. Dough will be thick.
5. Makes balls of about 2 tbsp of dough. Press cookie dough into the bottom and about 1/3-1/2 way up the sides of each cupcake cup, forming a cup shape.
6. Bake for 10-12 minutes, or until edges are just golden.
7. Remove from oven and allow to cool mostly in the pans, then remove to a cooling rack. If the centers aren’t cupped enough to add filling, use the end of a wooden spoon or the bottom of a tablespoon to press the center down a bit while still warm.
8. Once the cookies have cooled, make the cheesecake filling. Combine the pineapple juice and cornstarch in a small bowl. Microwave in 10 second increments until thickened, about 20-30 seconds. Set aside to cool.
9. Beat the cream cheese and powdered sugar together until smooth.
10. Add the pineapple juice mixture and crushed pineapple and mix until well combined.
11. Pipe or scoop cheesecake filling into cookie cups.
10. To make the whipped cream, add the heavy whipping cream, powdered sugar and coconut extract to a mixer bowl fitted with the whisk attachment. Whisk on high until it reaches stiff peaks.
12. Pipe whipped cream onto cookie cups, then top with a piece of pineapple and a cherry, if desired. Store in refrigerator.