Description
These Pineapple Upside Down Sugar Cookies combine classic pineapple upside-down cake flavors with the fun and convenience of a cookie. Featuring a buttery, soft sugar cookie topped with a caramelized brown sugar glaze, a juicy pineapple slice, and a maraschino cherry, this recipe is perfect for a unique dessert or sweet treat. Baked in a mini round cake pan, they have a delightful golden edge and a rich, tropical flavor that everyone will love.
Ingredients
Scale
Cookie Dough
- 1 cup butter (room temperature)
- 1 ½ cups granulated sugar
- 2 eggs
- 2 teaspoons vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- ½ teaspoon salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup melted butter
- 1 cup packed light brown sugar
Instructions
- Preheat the Oven and Prep the Pan: Preheat your oven to 350°F (175°C). Prepare a USA Pan mini round cake pan by ensuring it is clean and ready for the baking process.
- Mix the Cookie Dough: In a large mixing bowl, cream the room temperature butter and granulated sugar together until the mixture is light and fluffy. Add the eggs one at a time, mixing well after each addition, then stir in the vanilla extract and sour cream until fully incorporated. Gradually add the all-purpose flour, baking powder, cornstarch, and salt, mixing gently until the dough just comes together without overmixing.
- Prepare the Brown Sugar Glaze: In a separate bowl, stir together the melted butter and packed light brown sugar until the mixture is smooth and combined to create a luscious glaze.
- Assemble the Cookies: Drop about 1 tablespoon of the brown sugar glaze into the bottom cavity of each section of the mini round cake pan. Place one pineapple slice on top of the brown sugar in each cavity, and set a maraschino cherry in the center of each pineapple slice. Scoop approximately 3 tablespoons of the cookie dough and drop it gently onto the pineapple slice, flattening the dough slightly to cover the fruit evenly.
- Bake and Cool: Bake the assembled cookies at 350°F for about 25 minutes, or until the edges are golden brown and you see the brown sugar bubbling around the sides, indicating caramelization. Remove from the oven and let the cookies cool in the pan for 10 minutes to set before carefully turning them out onto wax paper. If needed, reposition the pineapple slices to ensure an appealing presentation. Allow the cookies to cool completely before serving.
- Storage Tips: Store the Pineapple Upside Down Sugar Cookies in an airtight container to keep them fresh. For optimal flavor and texture, enjoy them within 2-3 days.
Notes
- Use room temperature butter for easier creaming and better texture.
- Press the cookie dough gently to avoid breaking the pineapple slices.
- If the cookies stick when removing from the pan, allow them to cool longer or lightly grease the pan before assembling.
- These cookies can be made ahead and stored in a sealed container at room temperature.
- For a gluten-free version, substitute all-purpose flour with a gluten-free baking blend.
