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Pineapple Upside Down Sugar Cookies Recipe

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  • Author: Emily
  • Prep Time: 20 minutes
  • Cook Time: 25 minutes
  • Total Time: 45 minutes
  • Yield: 13cookies 1x
  • Category: Desserts
  • Method: Baking
  • Cuisine: American

Description

This delightful Pineapple Upside Down Sugar Cookies recipe combines the nostalgic charm of a classic pineapple upside-down cake with the delicious simplicity of a cookie! Each bite offers a soft, buttery cookie base topped with caramelized pineapple slices and sweet maraschino cherries. Perfect for parties, gatherings, or an indulgent treat at home, these cookies deliver both stunning presentation and incredible flavors.

Ingredients

Units Scale

For the Cookies

  • 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

For the Topping

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

Instructions

  1. Preheat Oven
    Preheat your oven to 350°F (175°C). Prepare a mini round cake pan or a similar cupcake pan, and set it aside.
  2. Cream the Butter and Sugar
    In a large mixing bowl, add the room-temperature butter and granulated sugar. Mix until the mixture is light and fluffy, indicating proper aeration.
  3. Incorporate Wet Ingredients
    Add the eggs, vanilla extract, and sour cream to the creamed butter mixture. Mix thoroughly until all the ingredients are well combined.
  4. Combine Dry Ingredients
    In the same bowl, gradually mix in the all-purpose flour, baking powder, cornstarch, and salt. Stir only until the dough comes together, being careful not to overmix. Set aside.
  5. Prepare the Brown Sugar Mixture
    In a separate bowl, stir together the melted butter and light brown sugar until fully combined. This will form the caramelized topping.
  6. Assemble the Layers
  7. Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of your prepared pan. Spread it evenly to cover the bottom.
  8. Place a pineapple slice on top of the brown sugar mixture and center a maraschino cherry in the middle of each pineapple slice.
  9. Top with Cookie Dough
    Using a 3-tablespoon cookie scoop, place a portion of the cookie dough on top of the pineapple layers. Use an offset spatula to gently flatten and level the dough.
  10. Bake and Set
    Place the pan in the oven and bake for 25 minutes, or until the edges turn golden brown and you can see the brown sugar mixture bubbling along the sides.
  11. Cool and Release
    Allow the cookies to cool in the pan for about 10 minutes. Gently turn them out onto a wax paper-lined surface to catch any excess caramelized sugar. If any pineapple pieces stick to the pan, simply reposition them on top of the corresponding cookie.
  12. Store and Serve
    Let the cookies cool completely before serving. Store them in an airtight container for up to 2–3 days for optimal freshness.

Notes

  • Sprinkle a small pinch of sea salt over the cookies after baking for a balance of flavors.
  • To make this recipe even more festive, use colored maraschino cherries.
  • Be sure to grease the pan thoroughly to help with the release of the topping and cookies.
  • Serve these cookies warm with a scoop of vanilla ice cream for an irresistible dessert!

Nutrition

  • Serving Size: 1 cookie
  • Calories: 310
  • Sugar: 35g
  • Sodium: 120mg
  • Fat: 15g
  • Saturated Fat: 9g
  • Unsaturated Fat: 6g
  • Trans Fat: 0g
  • Carbohydrates: 42g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 50mg

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