Description
These Pineapple Upside Down Sugar Cookies combine the classic flavors of the traditional pineapple upside-down cake with soft, buttery sugar cookies. Featuring a caramelized brown sugar and pineapple topping, each cookie is crowned with a juicy maraschino cherry, creating a delightful tropical treat perfect for parties or an indulgent snack.
Ingredients
Scale
Cookie Dough
- 1 cup butter, room temperature
- 1 ½ cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- ½ tsp salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Prepare the Brown Sugar Mixture: In a mixing bowl, combine the melted butter and packed light brown sugar until smooth and well combined. This mixture will create the caramelized base for the cookies.
- Line the Baking Pan: Using a muffin or cookie cavity pan, spoon approximately 1 tablespoon of the brown sugar mixture into the bottom of each cavity. Spread evenly to ensure the bottom is fully covered, which will help create the sticky, caramelized pineapple topping.
- Add Pineapple and Cherry: Place one canned pineapple slice on top of the brown sugar mixture in each cavity. Center a maraschino cherry in the middle of each pineapple slice making sure it’s slightly pressed down so it adheres to the mixture.
- Make the Cookie Dough: In a large bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, then stir in vanilla extract and sour cream until fully incorporated.
- Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add these dry ingredients to the wet ingredients, mixing until a smooth cookie dough forms. Avoid overmixing to keep the cookies tender.
- Assemble the Cookies: Drop cookie dough by approximately 2 tablespoons over each pineapple slice and cherry in the muffin pan, ensuring the topping remains mostly covered. Slightly smooth the tops if needed for an even shape.
- Bake the Cookies: Preheat the oven to 350°F (175°C). Bake the cookies for 18-22 minutes or until the edges are golden and the cookies appear set.
- Cool and Invert: Remove the pan from the oven and allow it to cool for 5-7 minutes. Carefully invert the pan onto a wire rack or serving plate to release the pineapple upside down cookies, revealing the caramelized fruit topping.
- Serve and Enjoy: Let the cookies cool completely before serving for best texture. These cookies pair wonderfully with a cup of tea or as a sweet tropical dessert.
Notes
- Use canned pineapple slices that are well-drained to prevent soggy cookies.
- Allow the cookies to cool slightly in the pan before inverting to avoid breaking.
- If you don’t have a muffin or cavity pan, small ramekins can be used as an alternative.
- Store cookies in an airtight container at room temperature for up to 3 days.
- For added texture, consider sprinkling chopped pecans or walnuts over the brown sugar mixture before adding the pineapple.
