Description
These Pineapple Upside Sugar Cookies bring the nostalgic flavors of pineapple upside-down cake into a soft, buttery cookie. Topped with caramelized pineapple slices and maraschino cherries, these cookies are a fun, tropical-inspired treat perfect for parties, dessert tables, or a sweet indulgence at home.
Ingredients
For the Cookies:
- 1 cup butter, room temperature
- 1 ½ cups granulated sugar
- 2 large 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 (drained)
- 13 maraschino cherries
- ½ cup melted butter
- 1 cup packed light brown sugar
Instructions
Step 1: Prepare the Cookie Dough
- In a large mixing bowl, cream together butter and granulated sugar until light and fluffy.
- Add eggs one at a time, beating well after each addition. Stir in vanilla extract and sour cream.
- In a separate bowl, whisk together flour, baking powder, cornstarch, and salt.
- Gradually mix dry ingredients into the wet ingredients until a soft dough forms.
- Cover and chill the dough in the refrigerator for at least 30 minutes.
Step 2: Prepare the Pineapple Topping
- Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.
- In a small bowl, mix melted butter and brown sugar to create a caramel mixture.
- Lay pineapple slices on the baking sheet and spoon 1 tablespoon of caramel mixture over each slice.
- Place a maraschino cherry in the center of each pineapple slice.
Step 3: Shape and Bake the Cookies
- Scoop 2 tablespoons of cookie dough and flatten it into a disc that matches the size of the pineapple slices.
- Place the dough discs on top of the pineapple slices, pressing gently.
- Bake for 12-14 minutes, or until the cookie edges are golden and the pineapple caramelizes.
- Let cookies cool on the baking sheet for 5 minutes, then carefully flip them over.
- Transfer to a wire rack to cool completely before serving.
Notes
- Coconut Twist: Add shredded coconut to the cookie dough for extra tropical flavor.
- Rum Flavoring: Stir in 1 teaspoon of rum extract for a more authentic pineapple upside-down cake taste.
- Spiced Version: Sprinkle a pinch of cinnamon or nutmeg into the brown sugar mixture.
- Mini Versions: Use pineapple tidbits instead of slices for bite-sized treats.
- Gluten-Free Option: Swap all-purpose flour with a 1:1 gluten-free baking blend.
- Prep Time: 40 minutes (including chilling time)
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
