Pineapple Upside-Down–Style Sugar Cookies bring the nostalgic charm of the classic cake into a delicate, bakery-style cookie that is both visually stunning and deeply aromatic. Buttery sugar cookie dough forms the base, topped with caramelized pineapple slices and bright cherries that melt gently into the surface as they bake. Moreover, these cookies are ideal for family gatherings, holiday trays, afternoon coffee breaks, or whenever you want a comforting dessert with a tropical twist.
Servings – Pineapple Upside-Down–Style Sugar Cookies
Servings: 18–20 cookies
Time Required for Pineapple Upside-Down–Style Sugar Cookies
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Prep Time: 20 minutes
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Cook Time: 14–16 minutes
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Total Time: 35–40 minutes
Ingredients for Pineapple Upside-Down–Style Sugar Cookies
Main Ingredients
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230 g unsalted butter, softened
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180 g granulated sugar
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1 large egg (about 55 g, room temperature)
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5 ml vanilla extract
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300 g all-purpose flour
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4 g baking powder
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2 g fine salt
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1 can pineapple slices in juice, drained well and cut into small rounds
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18–20 maraschino cherries, halved
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60 g light brown sugar
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30 ml pineapple juice (reserved from the can)
Optional Flavor Enhancers
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1 g ground cinnamon
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1 g ground nutmeg
Step-by-Step Instructions – How to Make Pineapple Upside-Down–Style Sugar Cookies
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Prepare the flavor base:
First, preheat the oven to 175°C and line two baking sheets with parchment paper. Meanwhile, whisk together the flour, baking powder, salt, and optional spices to evenly distribute the dry ingredients. -
Cream butter and sugar:
Next, beat the softened butter and granulated sugar until pale, light, and fluffy. This step is essential, as it incorporates air and ensures a tender cookie crumb. -
Incorporate egg and vanilla:
Then, add the egg and vanilla extract, mixing until fully emulsified. Moreover, scrape down the bowl to ensure a uniform mixture without dense butter pockets. -
Form the dough:
Gradually add the dry ingredients, mixing just until combined. However, avoid overmixing, as this can result in dense cookies. -
Prepare the pineapple topping:
In a small bowl, combine the brown sugar and pineapple juice. Next, spoon about half a teaspoon of this mixture onto each cookie portion after shaping the dough into balls and slightly flattening them. -
Assemble the cookies:
Then, gently press a pineapple piece into the center of each cookie and top with a cherry half. The sugar mixture will slowly caramelize during baking, creating the signature upside-down effect. -
Bake and finish:
Finally, bake for 14–16 minutes, until the edges are lightly golden and the centers are set. Allow the cookies to cool on the tray for 5 minutes before transferring to a rack, letting the caramelized topping settle beautifully.
Variations of Pineapple Upside-Down–Style Sugar Cookies
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With coconut: Add 40 g shredded coconut to the dough for a tropical bakery variation.
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Creamier version: Drizzle cooled cookies with a light cream cheese glaze for added richness.
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Spiced version: Increase cinnamon and nutmeg slightly and add a pinch of ground cloves for warmth.
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Seasonal swap: Replace pineapple with caramelized peaches or pears during autumn.
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Chocolate contrast: Dip the cooled cookie bases in dark chocolate for a modern twist.
Tips for Perfect Results – Pineapple Upside-Down–Style Sugar Cookies
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Control moisture: Pat pineapple pieces dry thoroughly; excess liquid can cause spreading and soggy centers.
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Even shaping: Keep cookie dough portions uniform to ensure even baking and consistent presentation.
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Enhance aroma: A touch of vanilla bean paste intensifies the buttery, caramelized notes.
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Storage: Store in an airtight container at room temperature for up to 3 days, or refrigerate for 5 days.
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Freezing: Freeze unbaked dough balls without topping for up to 2 months; add pineapple and cherries before baking.
Why Pineapple Upside-Down–Style Sugar Cookies Are Worth Making
Pineapple Upside-Down–Style Sugar Cookies perfectly balance nostalgia and elegance, offering crisp edges, soft centers, and a glossy caramelized fruit topping. Furthermore, they deliver a visually striking dessert that feels both homemade and bakery-refined. In addition, their adaptable nature allows endless variations without compromising texture or flavor.
Whether served warm with coffee or arranged on a festive platter, Pineapple Upside-Down–Style Sugar Cookies bring warmth, aroma, and timeless charm to any table.
