Pineapple Upside-Down Sugar Cookies
⏱ Time
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Prep: 20 minutes
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Bake: 12–14 minutes
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Total: ~35 minutes
🍽 Yield
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About 18–20 cookies
🛒 Ingredients
Pineapple Topping
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¼ cup unsalted butter, melted
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½ cup brown sugar (light or dark)
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6–7 pineapple rings, well-drained and cut into small pieces
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Maraschino cherries, halved (optional)
Sugar Cookie Dough
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½ cup unsalted butter, softened
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¾ cup granulated sugar
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1 large egg
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1 tsp vanilla extract
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1 ½ cups all-purpose flour
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½ tsp baking powder
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¼ tsp baking soda
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¼ tsp salt
🔪 Instructions
1. Prep the Pan
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Preheat oven to 350°F (175°C).
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Line a muffin tin with paper liners or lightly grease each cup.
2. Make the Pineapple Base
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Spoon 1 teaspoon melted butter into each muffin cup.
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Sprinkle 1 tablespoon brown sugar over the butter.
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Add a few pineapple pieces on top.
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Place a cherry half in the center (optional).
3. Make the Sugar Cookie Dough
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In a bowl, cream softened butter and sugar until light and fluffy.
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Beat in egg and vanilla.
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In a separate bowl, whisk flour, baking powder, baking soda, and salt.
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Gradually mix dry ingredients into wet ingredients until combined.
4. Assemble
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Scoop about 1½ tablespoons of cookie dough.
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Flatten slightly and place over the pineapple topping in each muffin cup.
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Gently press so the dough covers the fruit.
5. Bake
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Bake for 12–14 minutes, until lightly golden and set.
6. Flip & Cool
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Let cookies cool in the pan for 5 minutes.
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Carefully invert onto a baking sheet or plate.
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Cool slightly before serving.
⭐ Tips
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Drain pineapple very well to avoid soggy cookies.
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Don’t overbake — soft centers are best.
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Store in an airtight container for up to 3 days.
🍒 Optional Variations
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Coconut twist: Add ¼ tsp coconut extract to dough.
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Spiced: Add a pinch of cinnamon to the brown sugar layer.
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Mini version: Use a mini muffin tin (bake 8–10 minutes).
