Ingredients
Cooking spray
1 c. (2 sticks) butter, softened
1 c. packed brown sugar
1/2 c. granulated sugar
2 large eggs
1 tsp. pure vanilla extract
2 1/2 c. all-purpose flour
1 tsp. baking powder
1/2 tsp. ground cinnamon
1/2 tsp. kosher salt
1 (8-oz.) block cream cheese, softened
2 c. powdered sugar
1 tbsp. pineapple juice
1 tbsp. white rum
1/2 c. toasted sweetened coconut flakes, plus more for garnish
1 c. whipped cream topping
Pineapple wedges, for garnish
Maraschino cherries, for garnish
Preparation
Step 1Make cookie cups: Preheat oven to 350°. Grease 2 muffin tins with cooking spray. In a large mixing bowl, beat butter with sugars until light and fluffy. Add eggs and vanilla and mix until evenly combined. Add flour, baking powder, cinnamon, and salt and stir until just combined. Step 2Using a medium ice cream scoop, scoop dough into muffin tins and press down with a spoon. Bake until cookie cups are golden and set, about 15 to 20 minutes. (Don’t worry if the cookie cup centers rise!) Step 3While the cookies are still warm, turn them into cups: Spray the bottom of a small shot glass with cooking spray and press into the center of each cookie. Let cool in pan for 15 minutes, then transfer to wire cooling racks to cool completely. Step 4Meanwhile, make filling: In a large bowl using a hand mixer, beat cream cheese, powdered sugar, pineapple juice, and rum until smooth. Fold in toasted coconut.Step 5Pipe or scoop cream cheese filling into cookie cups. Dollop whipped cream on top, then garnish each cookie cup with toasted coconut, a pineapple wedge, and a maraschino cherry.
