Pineapple Upside Down Sugar Cookies – Tropical-Inspired Recipe

Pineapple Upside Down Sugar Cookies are a delightful twist on a classic dessert. Imagine the tropical flavors of pineapple and cherry nestled on a soft, fluffy sugar cookie base! These cookies capture the nostalgia of a pineapple upside-down cake in a fun, handheld treat. And yes—after that tasty topping of caramelized pineapple and cherry is gone, you’re left with a delicious sugar cookie that’s anything but boring. Whether you’re serving these for a summer gathering or simply treating yourself, they’re bound to impress!

Ingredients

For the cookies:

• 1 cup butter, room temperature
• 1 ½ cups granulated sugar
• 2 large eggs
• 2 tsp vanilla extract
• ½ cup sour cream
• 3 cups all-purpose flour
• 1 tsp baking powder
• 1 tsp cornstarch
• ½ tsp salt

For the topping:

• 13 canned pineapple slices
• 13 maraschino cherries
• ½ cup butter, melted
• 1 cup light brown sugar, packed

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Prep Your Oven and Pan

• Preheat your oven to 350°F (175°C).
• Set aside a USA mini round cake pan (or similar small molds) for baking.

Step 2: Make the Cookie Dough

1. Cream the Butter and Sugar
   In a large mixing bowl, cream the room-temperature butter and granulated sugar together until the mixture is light and fluffy.
2. Add Wet Ingredients
   Mix in the eggs, vanilla extract, and sour cream until smooth and combined.
3. Combine Dry Ingredients
   In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt. Gradually add this dry mixture to the wet mixture and stir until the cookie dough just comes together. Set aside.

Step 3: Prepare the Pineapple Topping

1. Make the Brown Sugar Mixture
   In a small bowl, stir together the melted butter and packed brown sugar until combined.
2. Assemble the Topping in Each Pan Cavity
   Add about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of the pan. Spread it around to cover the base evenly.
3. Add Pineapple and Cherry
   Place one pineapple slice over the brown sugar mixture and place a maraschino cherry in the center hole of each pineapple slice.

Step 4: Add Cookie Dough

• Scoop around 3 tablespoons of cookie dough over each pineapple slice and cherry. Use an offset spatula to flatten and spread the dough gently, covering the fruit entirely.

Step 5: Bake

• Bake in the preheated oven for about 25 minutes, or until the edges are golden and the brown sugar mixture is bubbling up around the sides.

Step 6: Cool and Release

• Let the cookies cool in the pan for about 10 minutes. Then, carefully turn each cookie out onto a wax paper-covered surface (this will catch any brown sugar runoff). If any pineapple slices stick to the pan, simply reposition them on the cookies.

Helpful Tips

• Greasing the Pan: Even if using a non-stick pan, a light spray of cooking spray will ensure easy release of the caramelized sugar topping.
• Room Temperature Butter: Start with room temperature butter for a smooth dough that comes together easily.
• Flattening the Dough: Flattening the dough evenly on top of each pineapple slice helps ensure the cookie bakes consistently and gets that golden-brown edge.

Substitutions and Variations

• Fruit Variations: Try peach slices or canned mango if you want a different tropical twist.
• Mini Muffin Pan Option: If you don’t have a mini cake pan, you can use a regular muffin pan; just cut the pineapple slices into smaller pieces to fit.
• Coconut Flakes: Sprinkle a little shredded coconut into the brown sugar mixture for an extra tropical flavor.

Frequently Asked Questions

Can I use fresh pineapple instead of canned?

Yes! Just make sure to slice it thinly and pat it dry before using to prevent excess moisture in the cookies.

Can I make the dough ahead of time?

Definitely. You can prepare the cookie dough up to 2 days in advance and store it in the fridge. Just bring it to room temperature before assembling.

Can these cookies be frozen?

Yes, you can freeze these cookies for up to 2 months. Wrap them individually to keep the topping intact and store in an airtight container.

Storage Instructions

Store the cookies in an airtight container at room temperature for up to 2-3 days. The topping will start to soften the cookie base after a couple of days, but they’ll still be delicious!

These Pineapple Upside Down Sugar Cookies are a tropical vacation in every bite! I’d love to hear how yours turn out—happy baking!

Pineapple Upside Down Sugar Cookies Recipe

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• Author: Zakia
• Total Time: 45 minutes
• Yield: 13 cookies 1x
• Diet: Vegetarian

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Description

Pineapple Upside Down Sugar Cookies combine a soft sugar cookie base with caramelized pineapple and cherry for a summery, tropical-inspired treat! With a buttery brown sugar topping that seeps into every bite, these cookies are perfect for parties, BBQs, or anytime you want a mini version of a classic dessert. Fun to make and delightful to eat, this recipe brings sunshine to every bite!

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Ingredients

Scale 1x2x3x

For the Cookies

• 1 cup butter, room temperature
• 1 ½ cups granulated sugar
• 2 large eggs
• 2 tsp vanilla extract
• ½ cup sour cream
• 3 cups all-purpose flour
• 1 tsp baking powder
• 1 tsp cornstarch
• ½ tsp salt

For the Topping

• 13 canned pineapple slices
• 13 maraschino cherries
• ½ cup butter, melted
• 1 cup light brown sugar, packed

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Instructions

• Preheat oven to 350°F (175°C). Set aside a mini round cake pan.
• In a large bowl, cream together room-temperature butter and granulated sugar until light and fluffy.
• Add eggs, vanilla extract, and sour cream to the bowl, mixing until combined.
• In a separate bowl, whisk together flour, baking powder, cornstarch, and salt. Gradually add this to the wet mixture until just combined. Set dough aside.
• In another bowl, combine melted butter and brown sugar. Spoon about 1 tablespoon of this mixture into each cavity of the cake pan, spreading to cover the bottom.
• Place a pineapple slice on top of the brown sugar mixture in each cavity, with a maraschino cherry in the center.
• Using a 3-tablespoon scoop, place cookie dough over the pineapple and cherry, flattening it slightly.
• Bake for 25 minutes, or until edges are golden and the brown sugar mixture is bubbling.
• Let cool in the pan for 10 minutes, then turn out onto wax paper to catch excess caramel. If any pineapple sticks to the pan, simply reposition it on the cookie.
• Allow cookies to cool completely before enjoying!

Notes

• For a different flavor, swap pineapple for peaches or mango slices.
• For best results, use room-temperature butter in the cookie dough.
• Store these cookies in an airtight container for up to 3 days at room temperature.

• Prep Time: 20 minutes
• Cook Time: 25 minutes
• Category: Dessert
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 1 cookie
• Calories: 315
• Sugar: 27g
• Cholesterol: 57mg