Description
Delicious pineapple upside-down sugar cookies that combine the classic flavors of pineapple upside-down cake with a chewy sugar cookie base.
Ingredients
Scale
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1/2 cup light brown sugar, packed
- 2 large eggs
- 2 teaspoons vanilla extract
- 2 3/4 cups all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1/2 teaspoon salt
- 1 can pineapple rings, drained and patted dry
- Maraschino cherries, drained
- 1/2 cup unsalted butter, melted (for topping)
- 1 cup light brown sugar (for topping)
Instructions
- Prepare the caramel topping by preheating your oven to 350°F (175°C). In a muffin tin, spoon a little melted butter into each cavity, followed by a sprinkle of brown sugar. This creates that rich caramel layer that makes pineapple upside-down desserts so special. The smell alone will remind you of classic holiday baking.
- Add the pineapple and cherries, cutting the pineapple rings into small pieces that fit neatly into the muffin cups. Place them over the brown sugar mixture and add a cherry in the center. Press them gently so they settle into the buttery sugar base.
- Make the sugar cookie dough in a large mixing bowl, cream the softened butter with granulated sugar and brown sugar until light and fluffy. This step creates that soft texture we love. Add the eggs one at a time, then stir in the vanilla extract. In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually mix the dry ingredients into the wet ingredients until just combined. The dough will be soft and slightly thick.
- Assemble the cookies by spooning dollops of cookie dough over each pineapple-filled muffin cavity. Gently spread the dough so it covers the fruit completely.
- Bake to golden perfection for 15–18 minutes, or until the tops are lightly golden. Let the cookies cool in the pan for about 5 minutes. Then carefully invert the pan onto a baking sheet or cooling rack. Watching them release with their glossy pineapple topping is one of the most satisfying parts of making Pineapple Upside-Down Sugar Cookies. Let them cool slightly before serving. The caramel will set as they rest.
Notes
- The caramel topping makes these cookies particularly special and adds a rich flavor.
- Ensure to drain the pineapple well to prevent excess moisture in the cookies.
- Prep Time: 20 minutes
- Cook Time: 18 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 250
- Sugar: 18g
- Sodium: 150mg
- Fat: 10g
- Saturated Fat: 6g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 34g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 40mg