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Pineapple Upside Down Sugar Cookies – Soft, Tropical & Bakery-Style

  • Author: amys recipes

Ingredients

Scale

For the Sugar Cookies

  • 1 cup (226 g) unsalted butter, softened

  • 1 cup granulated sugar

  • 1 large egg

  • 1 teaspoon vanilla extract

  • 2 1/2 cups all-purpose flour

  • 1/2 teaspoon baking powder

  • 1/4 teaspoon salt

For the Topping

  • 1/2 cup packed brown sugar

  • 1/4 cup unsalted butter, melted

  • 1 can pineapple slices or chunks, well drained

  • Maraschino cherries, halved

Instructions

Step 1: Prepare the Pineapple Topping

In a small bowl, mix the brown sugar and melted butter until combined. Set aside. Pat pineapple completely dry with paper towels to prevent excess moisture.

Step 2: Cream Butter and Sugar

In a large mixing bowl, beat softened butter and granulated sugar together until light and fluffy.

Step 3: Add Egg and Vanilla

Mix in the egg and vanilla extract until fully incorporated.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together flour, baking powder, and salt.

Step 5: Form the Dough

Gradually add the dry ingredients to the wet mixture, mixing just until combined. Do not overmix.

Step 6: Chill the Dough

Cover and refrigerate dough for 30 minutes. Chilling helps cookies hold their shape.

Step 7: Preheat and Prepare Baking Sheets

Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.

Step 8: Add the Topping

Place 1 teaspoon of brown sugar mixture on each cookie spot. Add a pineapple piece and top with a cherry half.

Step 9: Add Cookie Dough

Scoop about 2 tablespoons of cookie dough and gently place it on top of each pineapple topping. Lightly flatten.

Step 10: Bake

Bake for 12–15 minutes, until edges are set and bottoms are lightly golden.

Step 11: Flip and Cool

 

Allow cookies to cool for 5 minutes, then carefully flip them pineapple-side up. Let cool completely.

Notes

  • Drain pineapple thoroughly to avoid soggy cookies.

  • Flip cookies while warm to prevent sticking.

  • Do not overbake—the cookies should remain soft.

  • Use parchment paper for easy release.

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Find it online: https://recipesamys.com/pineapple-upside-down-sugar-cookies/