Pineapple Upside Down Sugar Cookies
Soft buttery sugar cookies topped with caramelized pineapple and a cherry center. All the flavor of the classic cake in a simple, bite-sized cookie.
Equipment
- Baking sheet
- Parchment paper
- Small saucepan
- Hand mixer or stand mixer
Ingredients
- 2 cups all-purpose flour
- 1/2 tsp baking powder
- 1/4 tsp salt
- 3/4 cup unsalted butter, softened
- 3/4 cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- 1 can (20 oz) pineapple rings, drained and patted dry
- 1/4 cup brown sugar
- 2 tbsp unsalted butter for caramel topping
- 12 maraschino cherries, halved one half per cookie
Instructions
- Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.
- Whisk together the flour, baking powder, and salt in a bowl. Set aside.
- Beat the softened butter and granulated sugar together until light and fluffy, about 2-3 minutes.
- Add the egg and vanilla extract. Mix until just combined.
- Stir in the flour mixture gradually until a soft dough forms. Do not overmix.
- Roll dough into 1.5-inch balls, place 2 inches apart on prepared sheets, and flatten slightly with your palm.
- Melt 2 tbsp butter with brown sugar in a small saucepan over medium heat. Stir until glossy, about 2 minutes.
- Cut pineapple into small pieces that fit each cookie. Press one piece onto each dough round.
- Spoon a small amount of brown sugar butter over each pineapple piece, then press a cherry half in the center.
- Bake for 12-14 minutes until edges are set and bottoms are lightly golden. Cool on the pan for 5 minutes before transferring.
Notes
- Pat pineapple pieces very dry to prevent cookies from spreading.
- Pull cookies out when centers look slightly underdone - they finish on the hot pan.
- Store in a single layer with parchment between layers for up to 3 days.