Description
These Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple upside down cake in an easy-to-make cookie form. With a buttery brown sugar base topped with juicy pineapple slices and maraschino cherries, these cookies are soft, sweet, and perfect for parties or a delightful dessert treat.
Ingredients
Scale
Cookie Dough
- 1 cup butter (room temperature)
- 1 1/2 cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- 1/2 cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- 1/2 tsp salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- 1/2 cup butter (melted)
- 1 cup light brown sugar (packed)
Instructions
- Preheat and prepare pan: Preheat the oven to 350°F (177°C). Set aside a USA pan mini round cake pan for assembling the cookies.
- Cream butter and sugar: In a large mixing bowl, beat the room temperature butter and granulated sugar together until the mixture is light and fluffy, which usually takes about 2-3 minutes.
- Add eggs, vanilla, and sour cream: Incorporate the eggs, vanilla extract, and sour cream into the butter mixture and mix until fully combined.
- Mix dry ingredients: In another bowl or directly, add the all-purpose flour, baking powder, cornstarch, and salt to the wet ingredients. Mix just until the cookie dough comes together; avoid overmixing to keep the cookies tender. Set the dough aside.
- Prepare brown sugar topping: In a small bowl, stir together the melted butter and light brown sugar until evenly combined, forming a syrupy mixture.
- Apply brown sugar base: Spoon about one tablespoon of the brown sugar mixture into the bottom of each cavity in the mini round cake pan. Spread evenly to cover the base well.
- Add pineapple and cherry: Place a canned pineapple slice on top of the brown sugar in each cavity, then press a maraschino cherry into the center of each pineapple slice.
- Add cookie dough: Using a 3-tablespoon cookie scoop, place cookie dough over each pineapple and cherry arrangement. Flatten the dough gently with an offset spatula to cover the toppings.
- Bake cookies: Bake the assembled cookies in the preheated oven for 25 minutes, or until the edges turn golden brown and the brown sugar topping bubbles up along the sides.
- Cool and invert: Allow the cookies to cool for 10 minutes in the pan. Then, invert the pan onto a wax paper-lined surface carefully, as the brown sugar topping may run and stick. If any pineapple slices stick to the pan, gently reposition them back on their respective cookies.
- Final cooling and storage: Let the cookies cool completely before serving. Store leftovers in an airtight container. For best taste and texture, consume within 2 to 3 days.
Notes
- Use wax paper when inverting the cookies to prevent sticking and to catch any sticky caramelized sugar that drips.
- If pineapple slices stick during removal, gently reposition them onto the cookie before serving.
- Room temperature butter is essential for creamy dough texture.
- Do not overmix the dough once the flour is added to maintain softness.
- Consume cookies within 2-3 days for optimal freshness.
