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.

Pineapple Upside Down Sugar Cookies

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• Author: Dulcia
• Total Time: 45 minutes
• Yield: 13 1x

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Description

Pineapple Upside Down Sugar Cookies are a delightful fusion of a classic dessert with a modern twist. These fluffy sugar cookies are topped with a golden slice of pineapple and a maraschino cherry, baked in a pool of buttery brown sugar that caramelizes into a sticky, sweet coating. Each bite offers a taste of tropical paradise with a perfect balance of sweetness and freshness.

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Ingredients

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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

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Instructions

Preheat your oven to 350°F (175°C). Prepare a mini round cake pan or similar by setting it aside.
In a large mixing bowl, cream the butter and granulated sugar together until light and fluffy.
Add in the eggs, vanilla extract, and sour cream. Mix until well combined.
In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until the cookie dough just comes together. Set aside.
In another bowl, mix together the melted butter and brown sugar until fully combined.
Add about a tablespoon of the brown sugar mixture to the bottom of each mini cake pan cavity, spreading it evenly.
Place a pineapple slice on top of the brown sugar mixture and position a maraschino cherry in the center of each pineapple.
Using a 3-tablespoon cookie scoop, portion the cookie dough and place it on top of each pineapple slice. Use an offset spatula to flatten the dough evenly.
Bake in the preheated oven for 25 minutes, or until the edges of the cookies are golden brown and the brown sugar mixture is bubbling around the sides.
Allow the cookies to cool in the pan for about 10 minutes. Then, carefully turn them out onto a wax paper-covered surface (to catch any excess brown sugar that may spill out). If any pineapples stick to the pan, gently reposition them on the cookies.
Let the cookies cool completely before serving. Store them in an airtight container. For the best flavor and texture, enjoy these cookies within 2-3 days.

• Prep Time: 20 minutes
• Cook Time: 25 minutes

Nutrition

• Calories: 310