These Pineapple Upside Sugar Cookies are soft, buttery, and topped with caramelized pineapple and cherries—just like the classic upside-down cake, but in cookie form! Perfect for parties, tea time, or summer desserts.
⏱ Prep Time
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Prep: 20 minutes
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Bake: 12–15 minutes
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Total: 35 minutes
Servings: 18–24 cookies
🥣 Equipment
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Mixing bowls
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Electric mixer
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Measuring cups & spoons
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Baking sheet
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Parchment paper
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Spoon or cookie scoop
🧈 Ingredients
Pineapple Topping
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1 cup pineapple tidbits (drained well)
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12–18 maraschino cherries (halved)
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¼ cup melted butter
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½ cup brown sugar
Sugar Cookie Dough
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1 cup unsalted butter (softened)
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1 cup granulated sugar
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1 large egg
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1 tsp vanilla extract
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2½ cups all-purpose flour
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1 tsp baking powder
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½ tsp salt
📝 Ingredient Notes
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Drain pineapple completely to avoid soggy cookies.
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You can use canned crushed pineapple, but tidbits give better texture.
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Light or dark brown sugar both work.
👩🍳 Instructions
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Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
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Prepare topping: Mix melted butter and brown sugar. Spoon a little onto each cookie spot. Add pineapple and a cherry piece on top.
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Make cookie dough: Cream butter and sugar until fluffy. Beat in egg and vanilla.
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In another bowl, mix flour, baking powder, and salt. Gradually add to wet mixture.
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Scoop dough and place on top of pineapple topping. Slightly flatten.
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Bake for 12–15 minutes until lightly golden.
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Let cool 5 minutes, then carefully flip cookies so pineapple is on top.
🧮 Nutrition Facts (per cookie, approx.)
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Calories: 160
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Carbohydrates: 22g
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Fat: 8g
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Protein: 2g
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Sugar: 12g
💡 Tips & Variations
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Add shredded coconut to the topping for tropical flavor.
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Drizzle with vanilla glaze for extra sweetness.
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Use gluten-free flour for a GF version.
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Serve warm with vanilla ice cream for a mini dessert treat.
