Ingredients
Scale
- 1 cup (2 sticks) unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 ¾ cups all-purpose flour
- 1 teaspoon baking powder
- ½ teaspoon salt
- For the Topping:
- ½ cup (1 stick) unsalted butter, melted
- ½ cup packed light brown sugar
- 1 can (8 oz) mini pineapple slices in juice, well drained
- 24 maraschino cherries, halved, patted dry
Instructions
- Cream together the softened butter and granulated sugar in a large bowl with an electric mixer until light and fluffy. Beat in the egg and vanilla extract until well combined.
- In a separate medium bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined and a soft dough forms. Do not overmix.
- Divide the dough in half, flatten each half into a disk, wrap in plastic wrap, and chill in the refrigerator for at least 30 minutes (or up to 2 days) to make it easier to handle.
- Preheat your oven to 375°F (190°C). Line two baking sheets with parchment paper or silicone mats.
- For the topping, evenly distribute the melted butter into the prepared baking sheet indentations. Sprinkle the brown sugar evenly over the melted butter. Place one mini pineapple slice on top of the brown sugar in each indentation, then place a halved maraschino cherry in the center of each pineapple ring.
- On a lightly floured surface, roll out one disk of chilled dough to about ¼-inch thickness. Using a round cookie cutter slightly larger than your mini pineapple slices (about 2.5 inches), cut out 24 cookie rounds.
- Carefully place each dough round on top of a prepared pineapple and cherry, gently pressing down to ensure good contact. Repeat with the remaining dough and topping ingredients.
- Bake for 10-12 minutes, or until the cookie edges are lightly golden. The pineapple topping will be bubbly.
- Immediately upon removing from the oven, let the cookies cool on the baking sheet for 5 minutes. Then, using a thin spatula, carefully invert each cookie onto a wire rack to allow the caramelized pineapple topping to set. Let cool completely before serving.
Notes
For best results, ensure your mini pineapple slices are very well drained to prevent the topping from becoming too watery. You can pat them dry with a paper towel. These cookies are best enjoyed fresh, but can be stored in an airtight container at room temperature for up to 3 days. A sprinkle of toasted shredded coconut after inverting adds an extra tropical touch!
- Prep Time: 25 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American (Tropical-Inspired)
Nutrition
- Serving Size: 1 cookie
- Calories: 180
- Sugar: 15g
- Sodium: 80mg
- Fat: 9g
- Saturated Fat: 5g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 23g
- Fiber: 0.5g
- Protein: 1.5g
- Cholesterol: 25mg