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Delicious Pineapple Upside-Down Cookies Recipe Easy & Fun

pineapple upside-down cookies - featured image

These pineapple upside-down cookies are the fun-sized version of the classic cake, packed with caramelized pineapple, buttery brown sugar, and a soft cookie base. Perfect for sharing and guaranteed to bring smiles to everyone’s faces!

Ingredients

Scale
  • 1 cup (226 g) unsalted butter, softened
  • 1 cup (200 g) granulated sugar
  • 2 large eggs, room temperature
  • 1 tsp vanilla extract
  • 2 ½ cups (315 g) all-purpose flour
  • 1 tsp baking powder
  • ¼ tsp salt
  • 1 cup (220 g) packed brown sugar
  • ½ cup (113 g) unsalted butter, melted
  • 12 pineapple rings (fresh or canned, drained)
  • 12 maraschino cherries

Instructions

  1. Preheat your oven to 350°F (175°C). Line your cookie sheets with parchment paper or silicone baking mats.
  2. Prepare the topping: In a small saucepot, melt the butter and stir in the brown sugar until smooth and bubbly. Set aside to cool slightly.
  3. Make the cookie dough: Cream the softened butter and granulated sugar together until light and fluffy, about 2-3 minutes. Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
  4. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Avoid overmixing!
  5. Shape the cookies: Scoop out about 2 tablespoons of dough and roll it into a ball. Flatten slightly into a disc about ½ inch thick. Repeat for the remaining dough.
  6. Assemble the cookies: Place a pineapple ring on top of each cookie disc. Spoon a small amount of the butter-brown sugar mixture into the center of the ring, then gently press a maraschino cherry into the middle.
  7. Bake: Bake the cookies for 12-15 minutes, or until the edges are golden brown and the topping is bubbly. Let the cookies cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.

Notes

[‘Pat the pineapple rings dry before using to prevent excess moisture.’, ‘Avoid overmixing the dough to ensure soft cookies.’, ‘Chill the dough for 15-20 minutes if your kitchen is warm to help the cookies hold their shape.’, ‘Keep an eye on the cookies during the last few minutes of baking to avoid burning the caramel topping.’]

Nutrition

Keywords: pineapple upside-down cookies, dessert, easy baking, caramelized pineapple, holiday treats