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Irresistible Pineapple Upside Down Sugar Cookies That Everyone Will Love - Featured Image

Irresistible Pineapple Upside Down Sugar Cookies That Everyone Will Love

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Learn how to make delicious Pineapple Upside Down Sugar Cookies. Easy recipe with step-by-step instructions.

  • Total Time: 45 minutes
  • Yield: 4 servings 1x

Ingredients

Scale

  • 2 ½ cups all-purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ¼ teaspoon salt
  • ¾ cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • ½ cup crushed pineapple, drained well (fresh or canned)
  • ¼ cup light brown sugar, packed
  • 2 tablespoons unsalted butter, melted (for topping)
  • Optional: 1 tablespoon pineapple juice (to brush on cookies)

Substitution Tips: If you want a dairy-free version, swap the butter for a plant-based margarine of equal parts. For a gluten-free twist, use a 1:1 gluten-free flour blend, but note that texture may vary slightly. If fresh pineapple isn’t available, canned pineapple drained thoroughly works just as well. For a little extra zing, adding a teaspoon of freshly grated ginger to the dough can deepen the flavor beautifully.

Instructions

  1. Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper. This step is key to prevent sticking and keep your cookies looking beautiful.
  2. In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Having these dry ingredients ready helps the process move smoothly.
  3. In a large bowl, use an electric mixer to cream the softened butter and granulated sugar until light and fluffy—this usually takes about 3 to 4 minutes. I always find this is the moment where the batter starts to feel like magic.
  4. Beat in the egg and vanilla extract until fully combined. This is where the dough starts to come alive, thick and glossy.
  5. Gradually add the dry ingredients to the wet mixture, mixing on low speed until just combined. Overmixing can lead to tougher cookies, so I always remind myself to stop as soon as the flour disappears.
  6. In a small bowl, stir together the crushed pineapple (drained well), brown sugar, and melted butter. This mixture will create that signature caramelized pineapple topping.
  7. Using a tablespoon or cookie scoop, drop dough balls onto the prepared baking sheets, spacing them about 2 inches apart.
  8. Press each dough ball gently with your fingers or the back of a spoon to create a small indentation in the center, then spoon about a teaspoon of the pineapple topping mixture onto each cookie, pressing lightly to adhere.
  9. Bake for 12-14 minutes, or until the edges are just golden and the cookies spring back softly when touched. The pineapple topping should be bubbling slightly and caramelized.
  10. Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely. I find this resting time helps the cookies set perfectly and keeps the topping intact.

  • Author: Jenny
  • Prep Time: 15 minutes
  • Cook Time: 30 minutes
  • Category: Main Dish
  • Method: Cooking
  • Cuisine: International