Pineapple Upside Down Sugar Cookies

These Pineapple Upside Down Sugar Cookies bring the classic pineapple upside-down cake into delicious, handheld cookies. Topped with caramelized pineapple and a cherry, each bite is soft, chewy, and bursting with tropical flavor. Perfect for when you want something fruity and sweet with a nostalgic twist!

The first time I made these Pineapple Upside Down Sugar Cookies, I was instantly reminded of childhood summers spent with my family. My husband and kids absolutely adore the bright flavor of pineapple, and these cookies are always a hit at family gatherings. My little ones especially love the cherry on top – they say it’s the best part! These cookies have quickly become a household favorite, bringing back memories of sunshine and fun every time I bake them.

Why You’ll Love Pineapple Upside Down Sugar Cookies

• Tropical Flavor: Sweet pineapple and maraschino cherries bring a bright, fruity flavor to every bite.
• Soft & Chewy Texture: The sugar cookie base is perfectly soft, balancing the caramelized topping.
• Easy to Make: Simple ingredients and no fancy tools required for these delightful treats.
• Fun Presentation: The beautiful pineapple and cherry topping makes these cookies as pretty as they are tasty.

Ingredients Notes for Pineapple Upside Down Sugar Cookies

• Pineapple Rings: Canned pineapple works great for this recipe. Cut each ring into small pieces to fit on top of the cookies.
• Maraschino Cherries: A classic touch that adds a pop of color and sweetness to each cookie.
• Brown Sugar: This helps create that lovely caramelization with the pineapple.
• Sugar Cookie Dough: You can use homemade or store-bought sugar cookie dough for convenience.

Recipe Steps for Pineapple Upside Down Sugar Cookies

Step 1: Preheat the Oven

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

Step 2: Prepare the Pineapple Topping

• In a small bowl, combine melted butter and brown sugar. Spoon a little mixture onto the lined baking sheet, where you’ll place each cookie.
• Cut the pineapple rings into small pieces. Place a few pieces of pineapple and a maraschino cherry half in the center of each brown sugar mixture on the baking sheet.

Step 3: Shape the Cookies

• Roll the sugar cookie dough into balls and slightly flatten them. Place each flattened dough ball on top of the pineapple and cherry mixture.

Step 4: Bake the Cookies

• Bake for 10-12 minutes, or until the cookies are golden and set around the edges. Let them cool on the baking sheet for a few minutes before transferring to a wire rack.

Step 5: Flip & Serve

• Once the cookies have cooled slightly, carefully flip each one to reveal the beautiful pineapple and cherry topping!

Storage Options

• Room Temperature: Store these cookies in an airtight container for up to 3 days.
• Refrigerator: They can be refrigerated for up to 5 days for longer freshness.
• Freezer: You can freeze the baked cookies for up to 2 months. Thaw at room temperature before serving.

Variations & Substitutions

• Use Fresh Pineapple: If you prefer, you can use fresh pineapple chunks instead of canned.
• Gluten-Free Option: Use gluten-free sugar cookie dough for a gluten-free version.
• Add Coconut: Sprinkle a little toasted coconut on top after baking for an extra tropical flair.
• Cookie Base Options: Experiment with different cookie dough bases like shortbread or snickerdoodle for a new twist.

Pineapple Upside Down Sugar Cookies

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Prep Time: 15 minutes minutes

Cook Time: 12 minutes minutes

Total Time: 30 minutes minutes

Servings: 12 cookies

Ingredients

 

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• ▢ For the Topping:
• ▢ 1/4 cup unsalted butter melted
• ▢ 1/2 cup brown sugar packed
• ▢ 6 pineapple rings cut each ring in half
• ▢ 6 maraschino cherries halved
• ▢ For the Sugar Cookie Dough:
• ▢ 1/2 cup unsalted butter softened
• ▢ 3/4 cup granulated sugar
• ▢ 1 large egg
• ▢ 1 teaspoon vanilla extract
• ▢ 1 1/2 cups all-purpose flour
• ▢ 1/2 teaspoon baking powder
• ▢ 1/4 teaspoon baking soda
• ▢ 1/4 teaspoon salt

Instructions

• Preheat Oven: Preheat your oven to 350°F (175°C). Line a 12-cup muffin tin with non-stick spray or grease well.
• Prepare the Topping: In each muffin cup, pour about 1 teaspoon of melted butter, then sprinkle 1 teaspoon of brown sugar over the butter. Place half of a pineapple ring in each cup, and then place a maraschino cherry in the center of each pineapple half.
• Prepare the Sugar Cookie Dough: In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until well combined.
• Mix Dry Ingredients: In another bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, mixing until just combined.
• Assemble the Cookies: Roll the cookie dough into 1-inch balls and slightly flatten them. Place a flattened ball of dough on top of each pineapple slice in the muffin tin.
• Bake: Bake in the preheated oven for 12-15 minutes, or until the edges of the cookies are lightly golden and the cookie dough is cooked through.
• Cool and Invert: Allow the cookies to cool in the tin for about 5 minutes. Carefully run a knife around the edges of each cookie and invert the muffin tin onto a wire rack, letting the cookies release upside down.
• Serve: Enjoy warm or at room temperature.