🍍 Pineapple Upside-Down Sugar Cookies
Ingredients
For the topping:
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1/4 cup (½ stick) unsalted butter, melted
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1/2 cup light brown sugar
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Maraschino cherries (about 12 halves or slices)
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Pineapple tidbits or small chunks (fresh or canned, drained)
For the cookies:
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2 ¾ cups all-purpose flour
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1 tsp baking soda
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½ tsp baking powder
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½ tsp salt
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¾ cup (1 ½ sticks) unsalted butter, softened
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1 cup granulated sugar
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½ cup brown sugar
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1 large egg
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2 tsp vanilla extract
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2 tbsp pineapple juice (from the can works great!)
Instructions
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Preheat oven: to 350°F (175°C). Grease a standard muffin pan.
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Make the topping:
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Mix melted butter and brown sugar together.
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Spoon about 1 teaspoon of the mixture into each muffin cup.
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Add a few pineapple tidbits and half a cherry on top of the sugar-butter layer.
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Make the cookie dough:
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In a medium bowl, whisk flour, baking soda, baking powder, and salt.
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In a large bowl, cream butter, granulated sugar, and brown sugar until light and fluffy (about 2 minutes).
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Beat in the egg, vanilla, and pineapple juice.
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Add dry ingredients gradually and mix until combined.
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Assemble:
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Scoop about 2 tablespoons of cookie dough and flatten slightly.
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Press each dough ball gently on top of the pineapple layer in the muffin tin.
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Bake:
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Bake for 12–15 minutes, until edges are golden and centers are set.
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Cool & flip:
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Let cookies cool in the pan for about 5 minutes, then carefully invert onto a wire rack or tray while warm.
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(If any fruit sticks, just spoon it back on top.)
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Optional: drizzle with a little glaze made from powdered sugar + pineapple juice.
🌺 Tips
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Use silicone muffin pans for easier release.
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For a tropical twist, sprinkle toasted coconut on top.
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Store at room temp for up to 3 days, or refrigerate for longer freshness.
Would you like me to give you a small-batch version (makes 6 cookies) or this full batch (makes 12)?
