This Pineapple Upside Down Sugar Cookies recipe turns the classic cake into soft, buttery cookies topped with caramelized pineapple and cherries—sweet, fruity, and impossible to resist in every bite.
Servings: 12
Ingredients
Pineapple Topping
- ¼ cup unsalted butter melted
- ½ cup light brown sugar packed
- 6 pineapple rings finely chopped (fresh or canned, well-drained)
- 6 maraschino cherries finely chopped
Sugar Cookie Dough
- ¾ cup unsalted butter softened
- ¾ cup granulated sugar
- 1 large egg room temperature
- 1 tsp vanilla extract
- 2 cups all-purpose flour
- ½ tsp baking powder
- ¼ tsp baking soda
- ¼ tsp salt
Instructions
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Preheat the oven to 350°F (175°C). Line two baking sheets with parchment paper.
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Prepare the pineapple base:
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In a small bowl, mix melted butter and brown sugar. Spoon about 1 tablespoon of this mixture onto the baking sheet for each cookie. Sprinkle chopped pineapple and cherry evenly over each butter-sugar pool.
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Make the cookie dough:
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In a large bowl, cream the softened butter and granulated sugar until light and fluffy. Add the egg and vanilla, mixing until smooth.
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Combine dry ingredients:
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In a separate bowl, whisk together flour, baking powder, baking soda, and salt. Gradually mix into the wet ingredients until a soft dough forms.
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Assemble the cookies:
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Scoop about 1½ tablespoons of dough and gently flatten it over each pineapple topping, covering it completely.
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Bake:
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Bake for 12–14 minutes, until the edges are lightly golden but centers remain soft.
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Flip and cool:
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Let cookies rest on the pan for 3–5 minutes, then carefully flip them upside down onto a cooling rack so the pineapple topping is on top. Cool completely before serving.