Pineapple Upside Sugar Cookies

Pineapple Upside Sugar Cookies: A Tropical Twist on a Classic Favorite

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Take your sugar cookies to the next level with these Pineapple Upside Sugar Cookies! A fruity, buttery treat with caramelized pineapple topping—perfect for summer parties or anytime you need a sweet escape.

Introduction

If you love the tropical flavor of pineapple and the buttery goodness of sugar cookies, you’re going to fall head over heels for these Pineapple Upside Sugar Cookies! Inspired by the classic pineapple upside-down cake, this fun twist brings that same sweet and tangy flavor into soft, chewy sugar cookies—no fork required.

Whether you’re hosting a summer BBQ, baking for the holidays, or just craving something unique, this recipe is sure to become a favorite. And bonus: these cookies are as beautiful as they are delicious.

🍪 Pineapple Upside Sugar Cookies Recipe

Ingredients

For the Topping:

• 1/2 cup brown sugar (light or dark)

• 2 tablespoons unsalted butter, melted

• 1/2 teaspoon cinnamon (optional)

• 1 can (8 oz) pineapple tidbits or chunks, drained and chopped

• Maraschino cherries, halved (optional, for garnish)

For the Sugar Cookie Dough:

• 1 cup unsalted butter, softened

• 1 cup granulated sugar

• 1/2 cup brown sugar

• 2 large eggs

• 1 tablespoon vanilla extract

• 2 ¾ cups all-purpose flour

• 1 teaspoon baking powder

• ½ teaspoon baking soda

• ½ teaspoon salt

Instructions

Step 1: Prepare the Pineapple Topping

1. In a small bowl, mix the brown sugar, melted butter, and cinnamon.

2. Line a muffin tin with non-stick spray or silicone liners.

3. Spoon 1 teaspoon of the brown sugar mixture into the bottom of each muffin cup.

4. Add a small amount of chopped pineapple on top. Add half a maraschino cherry in the center if desired.

Step 2: Make the Sugar Cookie Dough

1. Preheat your oven to 350°F (175°C).

2. In a large bowl, cream together butter, granulated sugar, and brown sugar until light and fluffy.

3. Add eggs one at a time, beating well. Stir in vanilla.

4. In a separate bowl, whisk together flour, baking powder, baking soda, and salt.

5. Gradually add the dry ingredients to the wet, mixing until combined.

Step 3: Assemble & Bake

1. Scoop a heaping tablespoon of cookie dough and press it over the pineapple mixture in each muffin cup.

2. Flatten gently with your fingers to cover the fruit.

3. Bake for 14–16 minutes, or until edges are golden brown.

4. Let cool for 5 minutes, then carefully invert the cookies onto a wire rack to cool completely. Use a knife to loosen edges if needed.