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Pineapple Upside Down Cookies


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  • Author: Chef MARTHA
  • Total Time: 30 minutes
  • Yield: 12 cookies
  • Diet: Vegetarian

Description

Pineapple Upside Down Cookies are a fun twist on the classic dessert, combining chewy, buttery cookie dough with caramelized pineapple, maraschino cherries, and brown sugar for a tropical treat.


Ingredients

  • 1 1/2 cups all-purpose flour
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 1/2 cup brown sugar, packed
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1/4 cup sour cream
  • 1/4 cup crushed pineapple, drained (reserve juice)
  • 12 maraschino cherries, halved (or one per cookie)
  • 2 tablespoons brown sugar (for the topping)

Instructions

  1. Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat.
  2. In a medium bowl, whisk together the flour, baking soda, and salt. Set aside. In a separate large bowl, beat the softened butter and brown sugar together until light and fluffy, about 2-3 minutes.
  3. Add the egg, vanilla extract, and sour cream to the butter mixture and beat until smooth and combined. Stir in the crushed pineapple, making sure it’s well-drained to avoid excess moisture.
  4. Gradually add the dry ingredients to the wet mixture, stirring until just combined. The dough should be soft but not too sticky.
  5. Scoop out about 1 tablespoon of dough and roll it into a ball. Place the dough balls on the prepared baking sheet, spacing them about 2 inches apart.
  6. Gently press a pineapple half into the center of each dough ball, then sprinkle a small amount of brown sugar (about 1/2 teaspoon) over each cookie. Add a maraschino cherry half on top of the pineapple.
  7. Bake for 10-12 minutes or until the edges are golden brown. The cookies will puff up slightly but should remain soft in the center.
  8. Let the cookies cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely.

Notes

  • For a tropical twist, sprinkle shredded coconut on top of the pineapple before baking.
  • Use fresh pineapple instead of canned for a fresher taste, ensuring it’s finely chopped and well-drained.
  • To make the cookies gluten-free, substitute the all-purpose flour with a gluten-free flour blend.
  • For an indulgent treat, drizzle melted chocolate over the cooled cookies.
  • Prep Time: 15 minutes
  • Cook Time: undefined
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180
  • Sugar: 15g
  • Sodium: 100mg
  • Fat: 8g
  • Saturated Fat: 4g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 26g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 20mg