Description
These Pineapple Upside Sugar Cookies are a delightful twist on the classic pineapple upside-down cake, transformed into individual cookie form. A buttery sugar cookie dough is paired with a sweet brown sugar glaze, juicy pineapple slices, and maraschino cherries, making for a tropical treat that’s perfect for any occasion.
Ingredients
Scale
For the Cookies:
- 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
For the Toppings:
- 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. Get your USA Pan mini round cake pan ready and set it aside.
- Mix the Cookie Dough: In a large mixing bowl, cream the butter and sugar together until light and fluffy. Add eggs, vanilla, and sour cream, and mix until well combined. Add flour, baking powder, cornstarch, and salt, and mix until the dough just comes together.
- Prepare the Brown Sugar Glaze: In another bowl, stir together melted butter and brown sugar until combined and smooth.
- Assemble the Cookies: Drop about 1 tablespoon of the brown sugar mixture into the bottom of each cavity in your pan. Place a pineapple slice on top and add a maraschino cherry in the center. Scoop 3 tablespoons of cookie dough on top of the pineapple, flattening it gently.
- Bake and Cool: Bake for about 25 minutes, or until the edges are golden and the brown sugar bubbles around the sides. Let cool in the pan for 10 minutes, then turn out onto wax paper. Reposition any pineapple if necessary. Cool completely before serving.
- Storage Tips: Store cookies in an airtight container and enjoy within 2-3 days for the best flavor.
Notes
- You can use fresh pineapple if preferred, but canned pineapple works best for consistent slices.
- Swap maraschino cherries for fresh cherries for a more natural flavor.
- The cookies can be served warm or at room temperature.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 290
- Sugar: 23g
- Sodium: 160mg
- Fat: 14g
- Saturated Fat: 9g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 40g
- Fiber: 1g
- Protein: 3g
- Cholesterol: 50mg