Description
These Pineapple Upside Down Sugar Cookies combine the classic tropical flavor of pineapple upside down cake with the delightful texture of sugar cookies. Each cookie features a juicy pineapple slice and a maraschino cherry on top, caramelized with a brown sugar and butter base, making them irresistibly sweet and perfect for gatherings or a fun dessert treat.
Ingredients
Scale
Cookie Dough
- 1 cup butter, room temperature
- 1 ½ cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- ½ tsp salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Prepare the brown sugar mixture: In a small bowl, combine the melted butter and light brown sugar until well mixed to form a consistent caramel-like base.
- Line the baking pan: Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of your prepared cookie pan or muffin tin. Spread it evenly to cover the bottom completely.
- Add fruit toppings: Place a canned pineapple slice on top of the brown sugar mixture in each cavity, then center a maraschino cherry in the middle of each pineapple slice to decorate.
- Make the cookie dough: In a large mixing bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla extract and sour cream until combined.
- Combine dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet mixture, mixing gently until a soft dough forms.
- Assemble the cookies: Drop spoonfuls of the cookie dough over the pineapple and cherry in each cavity, covering the fruit topping but not pressing down too hard so the caramel topping remains visible.
- Bake the cookies: Preheat your oven to 350°F (175°C). Bake the cookies for 20-25 minutes or until the edges are golden and a toothpick inserted near the cookie dough comes out clean.
- Cool and invert: Allow the cookies to cool in the pan for about 10 minutes. Carefully invert the pan onto a cooling rack or serving tray so the caramelized fruit topping is displayed on top of the cookies.
- Serve: Serve the pineapple upside down sugar cookies warm or at room temperature for the best flavor and texture experience.
Notes
- Use canned pineapple slices packed in juice, not syrup, to keep sugar levels balanced.
- Ensure the butter for the cookie dough is at room temperature for better creaming results.
- You can line the pan with parchment paper for easier removal or use silicone muffin molds.
- Store leftovers in an airtight container at room temperature for up to 3 days or refrigerate for longer freshness.
- For a more tropical twist, sprinkle a little shredded coconut on the dough before baking.
