Pineapple Upside Down Sugar Cookies
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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.
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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
Ingredients
- 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.
