Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies are a delightful twist on the classic pineapple upside-down cake. These charming cookies combine the buttery sweetness of traditional sugar cookies with the tropical flavors of pineapple and cherries, creating a dessert that is both visually appealing and delicious. Each cookie features a caramelized topping made from brown sugar, butter, juicy pineapple, and a maraschino cherry, giving it the signature look and flavor of the beloved cake.

The cookies begin with a soft and tender sugar cookie dough that is placed over a layer of pineapple and brown sugar. As the cookies bake, the topping caramelizes, creating a rich, golden glaze. Once baked and inverted, the pineapple and cherry topping becomes the star of the dessert, adding sweetness, moisture, and a beautiful presentation.

These cookies are perfect for parties, family gatherings, holidays, and special occasions. Their individual serving size makes them easy to share and enjoy without the need for slicing a cake. The combination of buttery cookie texture and fruity topping creates a wonderful balance of flavors that appeals to both children and adults.

Pineapple Upside Down Sugar Cookies offer a fun and creative way to enjoy a classic dessert in cookie form, making them a memorable treat for any occasion.

Prep Time: 20 minutes

Cook Time: 12–15 minutes
Total Time: 35 minutes
Servings: 18 cookies

Ingredients

For the Topping

• ¼ cup unsalted butter, melted
• ⅓ cup brown sugar
• 6 pineapple rings, drained and finely chopped
• 9 maraschino cherries, halved

For the Sugar Cookies

• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 2½ cups all-purpose flour
• 1 teaspoon baking powder
• ½ teaspoon salt

Instructions

1. Preheat your oven to 350°F (175°C). Grease a muffin tin or line a baking sheet with parchment paper.
2. In a small bowl, combine melted butter and brown sugar. Spoon about 1 teaspoon of the mixture into each muffin cup or onto the prepared baking sheet.
3. Add a small amount of chopped pineapple over the brown sugar mixture and place half a cherry in the center.
4. In a large bowl, cream together softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract.
5. In a separate bowl, whisk together flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture and mix until a soft dough forms.
6. Roll the dough into balls and flatten slightly. Place one cookie over each pineapple topping.
7. Bake for 12–15 minutes, or until the edges are lightly golden.
8. Allow the cookies to cool for 5 minutes, then carefully invert them onto a wire rack so the pineapple topping is on top.

Serving Suggestions

Serve warm or at room temperature. These cookies pair wonderfully with coffee, tea, or a scoop of vanilla ice cream.

Tips

• Pat the pineapple dry to prevent excess moisture.
• Refrigerate the dough for 15 minutes if it becomes too soft.
• Store cookies in an airtight container for up to 3 days.

Enjoy these sweet, buttery cookies inspired by the classic pineapple upside-down cake!

Read Also: Easy Colorful Summer Cookie Recipes