Here’s a delicious Pineapple Upside-Down Sugar Cookies recipe that blends the sweet, caramelized topping of a classic pineapple upside-down cake with the chewy goodness of sugar cookies!
🍍 Pineapple Upside-Down Sugar Cookies
🕒 Prep Time: 20 mins
🕒 Cook Time: 12–15 mins
🍪 Makes: ~24 cookies
🧾 Ingredients:
For the topping:
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1 can (20 oz) pineapple rings (drain & cut into small chunks)
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12 maraschino cherries (cut in halves)
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1/2 cup brown sugar
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1/4 cup unsalted butter, melted
For the sugar cookie dough:
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2 3/4 cups all-purpose flour
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1 tsp baking soda
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1/2 tsp baking powder
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1/2 tsp salt
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1 cup unsalted butter, softened
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1 1/2 cups granulated sugar
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1 egg
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1 tsp vanilla extract
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1–2 tbsp pineapple juice (from the can)
🧑🍳 Instructions:
1. Preheat & prep:
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Preheat oven to 350°F (175°C).
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Grease or line a muffin tin (regular size) — this helps create the “upside-down” effect.
2. Make the topping:
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In a bowl, mix melted butter and brown sugar.
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Spoon about 1 teaspoon of this mixture into each muffin cup.
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Add a few pineapple chunks and half a cherry into each cup on top of the brown sugar mix.
3. Make the sugar cookie dough:
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In a medium bowl, whisk together flour, baking soda, baking powder, and salt.
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In a large bowl, beat butter and sugar until fluffy (about 2-3 mins).
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Add egg, vanilla extract, and 1 tablespoon of pineapple juice. Mix well.
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Gradually add in dry ingredients until fully incorporated. If dough is too dry, add a bit more pineapple juice.
4. Assemble:
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Roll about 1 1/2 tbsp of dough into a ball and gently press it on top of the pineapple mixture in the muffin tin. Flatten slightly.
5. Bake:
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Bake for 12–15 minutes or until edges are lightly golden.
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Let cookies cool in the tin for 5–10 minutes, then carefully invert onto a wire rack or tray while still warm (use a knife around the edges if needed).
🍒 Tips:
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Serve warm for a gooey, cake-like experience.
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For a more caramelized effect, broil the tops for 1–2 minutes after flipping (optional).