Description
This Pineapple Upside Down Sugar Cookies recipe combines the classic flavors of pineapple upside down cake with the delightful texture of sugar cookies. With a buttery, soft cookie base topped with caramelized brown sugar, pineapple slices, and maraschino cherries, these cookies are a perfect treat for any occasion.
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, mix melted butter and packed light brown sugar until well combined. This mixture will caramelize under the pineapple to create the classic upside-down topping effect.
- Line the Pan: Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of a muffin or cupcake pan. Spread it evenly to cover the bottom completely.
- Add Pineapple and Cherry: Place one canned pineapple slice on top of the brown sugar mixture in each cavity. Center a maraschino cherry in the middle of each pineapple slice to add color and flavor.
- Make the Cookie Dough: In a large mixing bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Beat in eggs one at a time, then mix in vanilla extract and sour cream until smooth.
- Combine Dry Ingredients: In a separate bowl, sift together 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.
- Fill the Muffin Cups: Divide the cookie dough evenly and gently drop it over the pineapple and cherry topping in each muffin cavity, filling them about 2/3 full. Smooth the tops lightly for even baking.
- 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 into the center comes out clean.
- Cool and Invert: After baking, allow the cookies to cool in the pan for about 5 minutes. Carefully run a knife around the edges and invert each cookie onto a cooling rack or serving plate so the pineapple and cherry side is facing up.
- Serve: Let the cookies cool completely before serving to allow the caramelized topping to set. Enjoy these pineapple upside down sugar cookies fresh or store in an airtight container for up to 3 days.
Notes
- Using canned pineapple slices makes it easier to handle and ensures consistent sweetness.
- Be careful when inverting the cookies as the topping can be sticky and delicate.
- These cookies are best enjoyed within a few days for optimal freshness.
- Substitute vegan butter and egg replacers to make this recipe vegan-friendly.
