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Pineapple Upside Down Sugar Cookies Recipe

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4.7 from 102 reviews

Delight in these Pineapple Upside Down Sugar Cookies featuring a tender, buttery sugar cookie base topped with caramelized brown sugar, juicy pineapple slices, and a cherry in the center. Baked in individual mini cake pans, these cookies combine the nostalgic flavors of pineapple upside-down cake with the convenient sweetness of a cookie for a deliciously unique treat perfect for any occasion.

Ingredients

Scale

Cookie Dough

  • 1 cup butter (room temperature)
  • 1 1/2 cups granulated sugar
  • 2 eggs
  • 2 tsp vanilla extract
  • 1/2 cup sour cream
  • 3 cups all-purpose flour
  • 1 tsp baking powder
  • 1 tsp cornstarch
  • 1/2 tsp salt

Topping

  • 13 canned pineapple slices
  • 13 maraschino cherries
  • 1/2 cup butter (melted)
  • 1 cup light brown sugar (packed)

Instructions

  1. Preheat Oven and Prepare Pan: Preheat your oven to 350°F (175°C). Set aside a USA pan mini round cake pan for assembling your cookies.
  2. Create Cookie Dough Base: In a large mixing bowl, cream together the room temperature butter and granulated sugar until the mixture becomes light and fluffy, ensuring a smooth base for your cookies.
  3. Add Wet Ingredients: Beat in the eggs, vanilla extract, and sour cream until fully combined, creating a moist and flavorful dough.
  4. Incorporate Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt into the wet mix. Stir just until the dough comes together; avoid overmixing for tender cookies.
  5. Prepare Brown Sugar Mixture: In a separate bowl, combine the melted butter with the packed light brown sugar, mixing thoroughly for a rich caramel topping.
  6. Layer Brown Sugar Mixture: Spoon about one tablespoon of the brown sugar mixture evenly into the bottom of each cavity in the mini round cake pan. Spread it to cover the entire bottom surface.
  7. Add Fruit Toppings: Place one canned pineapple slice on top of the brown sugar layer in each cavity. Then, press a maraschino cherry into the center of each pineapple slice.
  8. Assemble Cookies: Scoop approximately 3 tablespoons of cookie dough onto each pineapple-topped cavity. Use an offset spatula to flatten the dough evenly over the fruit and sugar mixture.
  9. Bake: Place the pan in the preheated oven and bake for 25 minutes, or until the cookie edges turn golden brown and the brown sugar mixture is bubbling up the sides, indicating a perfectly caramelized finish.
  10. Cool and Unmold: Allow the cookies to cool in the pan for 10 minutes. Then, carefully invert the pan onto a wax paper-covered surface to release the cookies. The wax paper catches any running brown sugar. If the pineapple sticks to the pan, reposition it onto the cookie.
  11. Final Cooling and Storage: Let the cookies cool completely before serving. Store in an airtight container and enjoy within 2 to 3 days for optimal freshness.

Notes

  • Use wax paper when turning out the cookies to catch any sticky brown sugar drips.
  • If pineapple slices adhere to the pan during unmolding, gently reposition them on the cookie.
  • Room temperature butter is crucial for creaming to achieve a light and fluffy dough.
  • Cookies are best consumed within 2-3 days and stored airtight for freshness.
  • For easier portioning, use a 3-tablespoon cookie scoop for consistent cookie sizes.

Keywords: Pineapple upside down cookies, sugar cookies, pineapple cherry cookies, mini upside down cake cookies, baked pineapple desserts

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