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Pineapple Upside Down Sugar Cookie Recipe Card Perfect for anyone who loves pineapple upside down cookies!

Dreamy Pineapple Upside Down Sugar Cookies

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These Pineapple Upside Down Sugar Cookies are a delightful twist on a classic dessert. Soft, chewy sugar cookies are topped with caramelized pineapple and a sweet cherry, creating a burst of tropical flavor in every bite. The buttery caramel complements the tangy pineapple, while the sugar cookie provides a comforting and familiar base. These cookies are perfect for parties, holidays, or anytime you crave a sweet treat. The chewy texture of the cookie, combined with the soft pineapple and gooey caramel, makes for an unforgettable dessert experience. Prepare to be amazed by this unexpected combination of flavors and textures that will leave you wanting more!

  • Total Time: 37 minutes
  • Yield: 18 cookies 1x

Ingredients

Scale
  • 1/2 cup (1 stick) unsalted butter, softened
  • 3/4 cup granulated sugar
  • 1/4 cup packed light brown sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 1/4 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/4 cup milk
  • 1/4 cup unsalted butter, melted
  • 1/2 cup packed light brown sugar (for topping)
  • 1 (20 ounce) can pineapple slices, drained well and cut into smaller pieces
  • 18 maraschino cherries, halved

Instructions

  1. Preheat oven to 375°F (190°C). Line baking sheets with parchment paper.
  2. In a large bowl, cream together the softened butter, granulated sugar, and 1/4 cup brown sugar until light and fluffy. Beat in the egg and vanilla extract.
  3. In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, alternating with the milk, beginning and ending with the dry ingredients. Mix until just combined.
  4. In a small bowl, combine the melted butter and 1/2 cup brown sugar (for topping). Stir until smooth.
  5. Drop rounded tablespoons of cookie dough onto the prepared baking sheets. Use your fingers or the back of a spoon to flatten the cookies slightly.
  6. Spoon a small amount of the butter-brown sugar mixture onto each cookie. Top with a few pieces of pineapple and half a maraschino cherry.
  7. Bake for 10-12 minutes, or until the edges are lightly golden. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Notes

For best results, ensure the pineapple is well-drained to prevent soggy cookies. Store in an airtight container at room temperature for up to 3 days. You can also substitute canned crushed pineapple for the pineapple slices, if preferred. For a richer flavor, use dark brown sugar for the topping.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 185
  • Sugar: 15g
  • Sodium: 85mg
  • Fat: 8g
  • Saturated Fat: 5g
  • Unsaturated Fat: 2g
  • Trans Fat: 0g
  • Carbohydrates: 28g
  • Fiber: 0.5g
  • Protein: 1g
  • Cholesterol: 25mg
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