Pineapple Upside Down Sugar Cookies

These Pineapple Upside Down Sugar Cookies are a delightful twist on a classic dessert. With buttery sugar cookie dough, caramelized pineapple rings, and a cherry center, each bite delivers the perfect combination of tropical sweetness and soft, chewy cookie goodness. Ideal for parties or a fun weekend treat, these cookies are a sure way to brighten up your dessert table!

Ingredients:

• 1 cup butter, room temperature
• 1 ½ cups granulated sugar
• 2 eggs
• 2 teaspoons vanilla extract
• ½ cup sour cream
• 3 cups all-purpose flour
• 1 teaspoon baking powder
• 1 teaspoon cornstarch
• ½ teaspoon salt
• 13 canned pineapple slices
• 13 maraschino cherries
• ½ cup butter, melted
• 1 cup light brown sugar, packed

Directions:

1. Preheat the Oven:

Preheat your oven to 350°F (175°C). Set aside a mini round cake pan or a similar baking dish to prepare for the cookies.

2. Prepare the Cookie Dough:

In a large mixing bowl, cream the room-temperature butter and granulated sugar together until the mixture becomes light and fluffy. Add in the eggs, vanilla extract, and sour cream, mixing well until fully incorporated.

3. Mix the Dry Ingredients:

In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add this dry mixture to the wet ingredients, stirring until the dough just comes together. Set the cookie dough aside while you prepare the pineapple layers.

4. Make the Brown Sugar Mixture:

In another bowl, mix together the melted butter and packed brown sugar until fully combined. This will form the caramelized layer beneath the pineapple in each cookie.

5. Assemble the Pineapple Layer:

Add about a tablespoon of the brown sugar mixture to the bottom of each mini cake pan cavity, spreading it evenly. Next, place a pineapple slice on top of the brown sugar mixture, and position a maraschino cherry in the center of each pineapple ring.

6. Add the Cookie Dough:

Using a 3-tablespoon cookie scoop, portion out the cookie dough and place it on top of each pineapple slice. Use an offset spatula to flatten the dough evenly over the pineapple.

7. Bake the Cookies:

Bake the cookies in the preheated oven for about 25 minutes, or until the edges turn golden brown and the brown sugar mixture begins to bubble around the sides.

8. Cool and Flip the Cookies:

Let the cookies cool in the pan for about 10 minutes. Then, carefully turn them out onto a surface covered in wax paper to catch any excess brown sugar that may spill out. If any pineapples stick to the pan, gently reposition them on top of the cookies.

9. Serve and Store:

Allow the cookies to cool completely before serving. For the best results, store the cookies in an airtight container and enjoy them within 2-3 days.

Recipe Details:

• Prep Time: 20 minutes
• Cooking Time: 25 minutes
• Total Time: 45 minutes
• Calories: 310 kcal per cookie
• Servings: 13 cookies

These Pineapple Upside Down Sugar Cookies are the perfect mix of old-school charm and modern cookie appeal. The brown sugar caramelizes beautifully over the pineapple, creating a sweet and slightly sticky topping that pairs perfectly with the soft sugar cookie base. These cookies are as much fun to make as they are to eat, and they’re sure to be a favorite for any dessert lover.

Print