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Close-up of Pineapple Upside-Down Cookies topped with a cherry on a plate.

Pineapple Upside-Down Cookies


  • Author: Emma
  • Total Time: 32 min
  • Yield: 24 cookies 1x
  • Diet: Vegetarian

Description

These cookies capture the classic pineapple upside-down cake flavor in a chewy cookie form.


Ingredients

Scale
  • 1 cup (2 sticks) unsalted butter, softened
  • 1 1/2 cups granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 3 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup crushed pineapple, well-drained
  • 1/4 cup maraschino cherry halves, drained
  • 1/4 cup brown sugar

Instructions

  1. Preheat your oven to 350°F (175°C). Line baking sheets with parchment paper.
  2. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
  3. Beat in the eggs one at a time, then stir in the vanilla extract.
  4. In a separate bowl, whisk together the flour, baking soda, and salt.
  5. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
  6. Gently fold in the drained crushed pineapple.
  7. Drop rounded tablespoons of dough onto the prepared baking sheets, about 2 inches apart.
  8. Press a maraschino cherry half into the center of each cookie.
  9. Sprinkle the tops of the cookies with brown sugar.
  10. Bake for 10-12 minutes, or until the edges are lightly golden brown.
  11. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Notes

  • Ensure the crushed pineapple is very well-drained to prevent soggy cookies.
  • You can substitute chopped maraschino cherries if halves are unavailable.
  • For a stronger pineapple flavor, you can add 1 teaspoon of pineapple extract to the dough.
  • Prep Time: 20 min
  • Cook Time: 12 min
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180
  • Sugar: 15g
  • Sodium: 70mg
  • Fat: 8g
  • Saturated Fat: 5g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 25g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 30mg

Keywords: pineapple cookies, upside down cake cookies, fruit cookies, chewy cookies, dessert cookies