Pineapple Upside Down Cookie
This Pineapple Upside Down Cookie is a tropical twist on a classic dessert! Soft, chewy cookies topped with caramelized brown sugar, pineapple, and maraschino cherries.
Servings: 24 servings
Ingredients
- 1 cup unsalted butter softened for easy mixing
- 1 cup granulated sugar to sweeten the dough
- 2 large eggs room temperature for binding
- 1 cup all-purpose flour as the base of the cookie dough
- 1 teaspoon baking powder to help the cookies rise
- 0.5 teaspoon baking soda for a tender texture
- 0.25 teaspoon salt to balance the sweetness
- 1 teaspoon vanilla extract for warmth and depth
- 1 cup crushed pineapple well drained to avoid sogginess
- 0.5 cup packed brown sugar for that classic caramelized topping
- maraschino cherries for garnish and a burst of color
Instructions
- Set your oven to 350°F (175°C) and line a baking sheet with parchment paper.
- In a small bowl, combine the 1/2 cup packed brown sugar with a tablespoon of softened butter if you like, to help it caramelize beautifully. Set aside.
- In a large bowl, use your mixer to cream together the softened unsalted butter and granulated sugar until the mixture is pale and fluffy, about 2-3 minutes.
- One at a time, beat in the large eggs, making sure each is fully incorporated before adding the next. Stir in the vanilla extract.
- In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. Gradually add this to the butter mixture, mixing on low speed to avoid overworking the dough.
- Gently fold in the drained crushed pineapple with a spatula, distributing it evenly without breaking it down too much.
- Drop spoonfuls of the brown sugar mixture onto the lined baking sheet, then top each with a scoop of cookie dough. Press lightly to flatten slightly. Top each cookie with a maraschino cherry, gently pressing it into the dough.
- Bake for 12-15 minutes or until the edges are golden and the centers are set. Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a cooling rack to finish cooling.
Equipment
- Mixing Bowls
- Electric mixer or hand mixer
- Measuring cups and spoons
- Spatula
- Baking sheet lined with parchment paper
- Cooling rack
- Small spoon or cookie scoop
Notes
- Ensure the crushed pineapple is very well drained to prevent soggy cookies.
- Use room temperature butter and eggs for a smoother dough.
- Store cooled cookies in an airtight container at room temperature up to 4 days or freeze for longer storage.
- Swap maraschino cherries with natural juice-packed cherries for less sweetness.
- Add chopped nuts like pecans or walnuts for a nutty twist.