Description
These Pineapple Upside Sugar Cookies combine the tropical sweetness of pineapple and maraschino cherries with a buttery, soft sugar cookie base. Baked in a mini round cake pan, each cookie features a caramelized brown sugar and butter topping that mimics the classic pineapple upside-down cake flavor in a delightful cookie form. Perfect for gatherings or a sweet treat, these cookies are easy to make and irresistibly delicious.
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 and Prepare Pan: Preheat your oven to 350°F (175°C) and lightly grease a mini round cake pan to prevent sticking.
- Cream Butter and Sugar: In a large bowl, use a 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: Beat in the eggs, vanilla extract, and sour cream until the mixture is well combined and smooth.
- Combine Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt into the wet ingredients, mixing until a soft dough forms.
- Prepare Brown Sugar Mixture: In a separate bowl, stir together the melted butter and packed light brown sugar until the sugar is moistened evenly.
- Assemble Cookies: Spread about 1 tablespoon of the brown sugar mixture evenly into each mini cake pan cavity. Place a pineapple slice on top of the brown sugar in each cavity, then center a maraschino cherry on each pineapple slice.
- Add Cookie Dough: Drop approximately 3 tablespoons of cookie dough on top of each pineapple slice and gently press the dough to cover the fruit completely.
- Bake Cookies: Bake in the preheated oven for 25 minutes, or until the cookies turn golden brown on top.
- Cool and Serve: Let the cookies cool in the pan for 10 minutes to set, then carefully invert them onto wax paper or a cooling rack to cool completely before serving.
Notes
- Use room-temperature butter for easier creaming and better texture.
- Press the dough gently over the pineapple to keep the fruit intact during baking.
- Use mini round cake pans or an equivalent muffin tin if mini pans are unavailable.
- Ensure cookies are fully cooled before removing from the pan to maintain shape.
- For a dairy-free version, substitute sour cream with a dairy-free yogurt alternative.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
