Description
These Pineapple Upside Down Sugar Cookies combine the tropical sweetness of pineapple and maraschino cherries with classic sugar cookie dough, baked to golden perfection. Each mini cookie features a caramelized brown sugar and butter base topped with a pineapple slice and cherry, creating a delightful twist on the traditional upside-down cake in cookie form. Perfect for a sweet treat or a festive gathering.
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 Oven and Prepare Pan: Preheat your oven to 350°F (175°C). Lightly grease a mini round cake pan to prevent sticking and ensure easy removal of the cookies.
- Cream Butter and Sugar: In a large mixing bowl, use a hand mixer or stand mixer to cream together the room temperature butter and granulated sugar until the mixture is fluffy and light, which helps create a tender cookie texture.
- Add Wet Ingredients: Mix in the eggs, vanilla extract, and sour cream until completely combined, creating a smooth batter that will lend moisture and richness to your cookies.
- Incorporate Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt into the wet mixture. Stir until a cohesive dough forms, being careful not to overmix to maintain a tender crumb.
- Prepare Brown Sugar Mixture: In a separate small bowl, combine the melted butter and light brown sugar. Mix well until smooth to create a caramel-like topping base.
- Add Toppings to Pan: Spread about 1 tablespoon of the brown sugar mixture evenly into each cavity of the mini cake pan. Then place one pineapple slice atop each brown sugar layer, pressing slightly. Center a maraschino cherry on each pineapple slice for the classic look and sweet flavor.
- Top with Cookie Dough: Spoon roughly 3 tablespoons of cookie dough over each pineapple slice, gently pressing the dough to cover the fruit but avoiding squeezing the cherry out of place.
- Bake the Cookies: Place the pan in the preheated oven and bake for approximately 25 minutes, or until the cookies turn golden brown and are set around the edges.
- Cool and Serve: Allow the cookies to cool in the pan for 10 minutes to set the toppings and prevent breaking. Then carefully turn out the cookies onto wax paper or a wire rack to cool completely before serving.
Notes
- Make sure the butter is at room temperature to ensure proper creaming with the sugar.
- Use canned pineapple slices for convenience and consistent size; drain well to avoid excess moisture.
- If you don’t have a mini round cake pan, mini muffin pans can be used as an alternative, adjusting dough quantity accordingly.
- For a stronger caramel flavor, you can use dark brown sugar instead of light brown sugar.
- Allow cookies to cool completely before removing from the pan to keep toppings intact.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
