Description
These Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple upside-down cake with the simplicity and convenience of sugar cookies. Each cookie features a soft, buttery dough topped with a caramelized brown sugar base, a sweet pineapple slice, and a maraschino cherry, baked to golden perfection for a delightful tropical 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 topping: In a bowl, mix the melted butter and the packed light brown sugar until well combined. This mixture will create the caramelized base for your cookies.
- Fill the pan cavities: Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of a prepared muffin or cookie pan. Spread it evenly covering the bottom completely to ensure a sticky, caramelized base.
- Add pineapple and cherries: Place one 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. This forms the classic upside-down cookie topping.
- 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, followed by vanilla extract and sour cream until well combined.
- Combine dry ingredients and mix: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined to form a soft dough.
- Assemble and bake: Drop or spoon the cookie dough evenly over the pineapple and cherry topping in each cavity, covering them completely. Bake in a preheated oven at 350°F (175°C) for 18-22 minutes or until the edges are golden and a toothpick inserted in the dough comes out clean.
- Cool and invert: Allow the cookies to cool in the pan for about 5 minutes. Then carefully invert the pan onto a wire rack or serving dish so the pineapple and cherries become the top of the cookie. Let them cool completely before serving.
Notes
- Use a non-stick muffin tin or grease your pan well to prevent sticking when inverting the cookies.
- You can substitute fresh pineapple slices if preferred; just drain them well.
- For a softer cookie, avoid overbaking; check for doneness at 18 minutes.
- Store cookies in an airtight container at room temperature for up to 3 days.
- For added flavor, sprinkle a pinch of cinnamon in the brown sugar mixture before assembling.
