Description
Delight in these Pineapple Upside-Down Cookies that capture the tropical sweetness of pineapple and cherries in every bite. Soft, buttery cookie dough is infused with juicy crushed pineapple and maraschino cherries, then topped with a caramelized pineapple and brown sugar glaze. Perfectly baked to golden edges, these cookies bring the flavors of a classic pineapple upside-down cake into a convenient handheld treat.
Ingredients
Scale
Cookie Dough
- 1/2 cup unsalted butter, softened
- 3/4 cup brown sugar, packed
- 1/4 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
- 1/2 cup crushed pineapple, well drained
- 1/3 cup maraschino cherries, chopped
Topping
- 1/4 cup pineapple juice
- 2 tablespoons melted butter
- 1/4 cup brown sugar
Instructions
- Preheat and Prepare Baking Sheet: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking and ease cleanup.
- Cream Butter and Sugars: In a large bowl, cream together the softened unsalted butter, packed brown sugar, and granulated sugar using a mixer or by hand until the mixture is light and fluffy, about 2-3 minutes.
- Add Egg and Vanilla: Beat in the large egg and vanilla extract until the mixture is well combined and smooth.
- Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to evenly distribute the leavening and seasoning.
- Combine Dry and Wet Mixtures: Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms without overmixing.
- Fold in Fruit: Gently fold the well-drained crushed pineapple and chopped maraschino cherries into the dough, ensuring even distribution without breaking the fruit down too much.
- Prepare Topping Mixture: In a small bowl, combine the melted butter, pineapple juice, and brown sugar, stirring until smooth and well blended to create the cookie topping glaze.
- Portion Cookies: Scoop tablespoon-sized portions of the cookie dough onto the lined baking sheet, spacing them adequately to allow for spreading during baking.
- Add Topping: Spoon a small amount of the pineapple-butter-brown sugar topping mixture over the center of each cookie dough portion to give that characteristic pineapple upside-down effect.
- Bake: Bake the cookies in the preheated oven for 12 to 14 minutes or until the edges are lightly golden and the cookies are set.
- Cool: Let the cookies cool on the baking sheet for a few minutes to set before transferring them to a wire rack to cool completely and finish firming up.
Notes
- Drain the pineapple very well to prevent cookies from spreading excessively.
- For a stronger pineapple flavor, add a small splash of pineapple extract to the dough or topping.
- Due to the fruit content, store these cookies in an airtight container in the refrigerator to maintain freshness.
