Pineapple Upside-Down Sugar Cookies: A Tropical Twist on a Classic Treat

For the Pineapple Topping:

• 1 cup fresh pineapple, finely chopped (or canned pineapple, drained and diced)

• ¼ cup brown sugar (light or dark)

• 2 tablespoons unsalted butter

• 10-12 maraschino cherries, drained and halved (or you can use fresh cherries in season)

🔪 Preparation

Step 1: Prepare the Pineapple Topping

The pineapple topping is what makes these cookies truly special, and it all begins with caramelizing the pineapple.

1. Sauté the Pineapple: In a small saucepan over medium heat, melt 2 tablespoons butter. Add 1 cup finely chopped fresh pineapple and sauté for about 5 minutes, stirring occasionally, until the pineapple softens and releases its juices.

2. Add Brown Sugar: Stir in ¼ cup brown sugar and continue to cook for another 3-4 minutes, until the mixture becomes syrupy and the sugar fully dissolves. The pineapple should be golden and glossy.

3. Cool the Pineapple Mixture: Remove from the heat and let the caramelized pineapple mixture cool to room temperature.

Step 2: Make the Sugar Cookie Dough

Now, it’s time to prepare the dough for the sugar cookies that will form the base of our upside-down treat.

1. Cream the Butter and Sugar: In a large mixing bowl, beat 1 cup of softened butter and 1 cup of granulated sugar until light and fluffy, about 3-4 minutes with an electric mixer or a stand mixer fitted with the paddle attachment.

2. Add Egg and Vanilla: Add 1 large egg and 1 teaspoon vanilla extract to the butter mixture. Beat until fully incorporated.

3. Combine Dry Ingredients: In a separate bowl, whisk together 2 ¼ cups all-purpose flour, ½ teaspoon baking powder, ¼ teaspoon baking soda, and ¼ teaspoon salt. Gradually add the dry ingredients to the wet ingredients in two additions, mixing just until combined.

4. Add Cream: Add 2 tablespoons of heavy cream to the dough and mix until smooth. The dough should be soft but slightly firm and easy to scoop.

Step 3: Form the Cookies

1. Preheat the Oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.

2. Scoop the Dough: Using a cookie scoop or tablespoon, scoop 1 ½-inch balls of dough and place them on the prepared baking sheet, leaving about 2 inches between each cookie.

3. Flatten the Dough: Lightly flatten each dough ball with the palm of your hand or the back of a spoon to form a slightly thick round. This will allow for even cooking and a good surface area for the pineapple topping.

Step 4: Add the Pineapple Topping

Now comes the fun part — topping the cookies with the caramelized pineapple!

1. Top the Dough: Spoon about 1 tablespoon of the caramelized pineapple mixture onto each flattened cookie dough ball. Make sure to spread it out slightly but leave a little space around the edges.

2. Add a Cherry: Place a maraschino cherry half on top of the pineapple topping for that signature upside-down look.

Step 5: Bake the Cookies

1. Bake the Cookies: Place the baking sheet in the preheated oven and bake for 12–15 minutes, or until the edges of the cookies are lightly golden. The pineapple topping should be bubbly and caramelized, and the cookies should be firm to the touch but slightly soft in the center.

2. Cool the Cookies: Allow the cookies to cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely.

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