1. Tropical Flavor : Juicy pineapple chunks add a bright, tangy sweetness that complements the buttery cookie base.
2. Caramelized Topping : The brown sugar and pineapple create a sticky, caramel-like layer reminiscent of the classic cake.
3. Easy to Make : Simple ingredients and straightforward steps make this recipe approachable for bakers of all levels.
4. Perfect for Sharing : These cookies are bite-sized and portable, making them ideal for gatherings or gifting.
5. Unique & Fun : A playful twist on traditional cookies that’s sure to impress.

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Ingredients You’ll Need

Makes 24–30 cookies

For the Pineapple Topping:

• 1 cup crushed pineapple , drained (reserve the juice for the cookie dough)
• 1/4 cup packed brown sugar
• 1 tbsp unsalted butter , melted

For the Cookie Dough:

• 1 cup unsalted butter , softened
• 1 cup granulated sugar
• 1 large egg
• 1 tsp vanilla extract
• 2 cups all-purpose flour
• 1/2 tsp baking powder
• 1/4 tsp salt
• 2–3 tbsp reserved pineapple juice

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Step-by-Step Instructions

Step 1: Preheat & Prep

1. Preheat your oven to 350°F (175°C) . Line a baking sheet with parchment paper or silicone baking mats.

Step 2: Make the Pineapple Topping

1. In a small bowl, mix the drained crushed pineapple, brown sugar, and melted butter until well combined.
2. Drop small spoonfuls (about 1 teaspoon each) of the pineapple mixture onto the prepared baking sheet, spacing them about 2 inches apart.

Step 3: Make the Cookie Dough

1. In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy (about 2–3 minutes).
2. Beat in the egg and vanilla extract until smooth.
3. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
4. Add 2–3 tablespoons of the reserved pineapple juice to the dough, 1 tablespoon at a time, until the dough reaches a soft, scoopable consistency.

Step 4: Assemble the Cookies

1. Scoop about 1 tablespoon of cookie dough and roll it into a ball. Place the dough ball directly on top of each pineapple topping dollop.
2. Gently press down on the dough to slightly flatten it and help it adhere to the pineapple layer.

Step 5: Bake

1. Bake for 10–12 minutes , or until the edges are lightly golden and the cookies are set.
2. Remove from the oven and let the cookies cool on the baking sheet for 5 minutes.

Step 6: Flip the Cookies

1. Carefully flip each cookie over using a spatula to reveal the caramelized pineapple topping underneath. Let cool completely before serving.

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Why This Recipe Works

• Pineapple Juice Magic : Adds a subtle sweetness and moisture to the cookie dough without overpowering it.
• Caramelized Layer : The brown sugar and butter caramelize during baking, creating a sticky, gooey topping.
• Soft & Chewy Texture : The sugar cookie base is perfectly tender and pairs beautifully with the juicy pineapple.

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Variations to Try

• Add Nuts : Sprinkle chopped pecans or macadamia nuts over the pineapple topping for extra crunch.
• Glaze It Up : Drizzle a simple glaze (powdered sugar + reserved pineapple juice) over the cooled cookies for added sweetness.
• Spice It Up : Add a pinch of cinnamon or nutmeg to the cookie dough for a warm, spiced flavor.
• Mini Cookies : Use smaller portions of dough and pineapple topping for bite-sized treats.
• Coconut Twist : Stir shredded coconut into the cookie dough or sprinkle it over the pineapple topping for a tropical flair.

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Tips for Success

• Drain the Pineapple Well : Excess liquid can make the topping too runny—pat it dry with a paper towel if needed.
• Don’t Skip the Flip : Flipping the cookies reveals the beautiful caramelized pineapple layer, so handle them gently.
• Storage : Store leftovers in an airtight container at room temperature for up to 3 days.

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Serving Suggestions

• Romantic Touch : Garnish with a sprinkle of powdered sugar or a tiny edible flower for elegance.
• Brunch Staple : Serve alongside coffee, tea, or mimosas for a light breakfast treat.
• Party Platter : Pair with other tropical desserts like coconut macaroons or key lime pie for variety.

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Final Thoughts

These Pineapple Upside Sugar Cookies are a delightful fusion of tropical flavors and classic cookie charm. With their caramelized pineapple topping, soft sugar cookie base, and customizable options, they’re a recipe that feels indulgent yet approachable. Whether you’re serving them for a special occasion, a casual dessert, or simply craving something sweet, these cookies are sure to bring smiles and satisfaction.

Your turn! Have you ever made cookies inspired by a cake before? Share your favorite variations or serving ideas below. 🍍