Description
Pineapple Upside Down Cookies: Soft, buttery cookies with caramelized pineapple slices on top. Quick, comforting, and crowd-pleasing treat.
Ingredients
Scale
- 4 tablespoons (56g) unsalted butter
- 3/4 cup (150g) brown sugar, packed
- 1 can (20 oz/567g) pineapple rings, drained well (reserve 2 tablespoons juice for the cookie dough)
- 20–24 maraschino cherries, drained and patted dry
- 2 1/2 cups (313g) all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon baking soda
- 1/2 teaspoon salt
- 3/4 cup (170g) unsalted butter, softened
- 1 cup (200g) granulated sugar
- 1/4 cup (50g) brown sugar, packed
- 2 large eggs, room temperature
- 1 teaspoon vanilla extract
- 2 tablespoons reserved pineapple juice
- 1/2 teaspoon almond extract (optional)
Instructions
- Step 1: Prepare the Caramelized Pineapple Topping Start by lining two baking sheets with parchment paper or silicone mats. In a medium saucepan over medium heat, melt the butter completely. Add the brown sugar and stir continuously until the mixture becomes smooth and bubbling, about 3-4 minutes. Remove from heat. Using a tablespoon, spoon 20-24 small circles of the caramel mixture onto the prepared baking sheets, spacing them at least 3 inches apart. Place one pineapple ring on each caramel circle, then add a maraschino cherry in the center of each ring. Place the baking sheets in the freezer while you prepare the cookie dough.
- Step 2: Make the Cookie Dough Preheat your oven to 350°F (175°C). In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. In a large bowl or stand mixer, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy, about 3 minutes. Add eggs one at a time, beating well after each addition. Mix in the vanilla extract, reserved pineapple juice, and almond extract if using. Gradually add the dry ingredients to the wet ingredients, mixing on low speed just until combined. The dough will be soft and somewhat sticky.
- Step 3: Assemble and Bake the Cookies Remove the prepared topping from the freezer. Using a cookie scoop or spoon, place about 2 tablespoons of dough on top of each pineapple ring. Gently press and shape the dough to cover the pineapple completely, being careful not to disturb the placement of the pineapple and cherry. Bake for 12-14 minutes, until the cookies are just set and the edges are lightly golden. The centers should still be soft. Allow the cookies to cool on the baking sheets for 10 minutes before carefully transferring them to a wire rack to cool completely.
- Step 4: Finishing Touches Once the cookies are completely cool, you may notice some caramel has pooled around the edges. This is perfectly normal and adds to their homemade charm! If desired, you can trim any excess caramel with kitchen scissors for a neater presentation. For an extra touch of sweetness and shine, brush the pineapple and cherry topping with a thin layer of warmed apricot jam or a simple glaze made from powdered sugar and pineapple juice.
Notes
Fresh ingredients will always yield the best flavor results.
Nutrition
- Serving Size: 1 cookie
- Calories: 230 calories per serving
- Sugar: 15g
- Sodium: 170mg
- Fat: 10g
- Saturated Fat: 6g
- Unsaturated Fat: 4g
- Trans Fat: 0g
- Carbohydrates: 32g
- Fiber: <1g
- Protein: 2g
- Cholesterol: 40mg