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Pineapple Upside Down Cookies

Pineapple Upside Down Cookies

Pineapple Upside Down Cookies are delightful sweet treats bursting with tropical pineapple flavor and caramelized brown sugar notes. Inspired by the classic pineapple upside down cake, these portable, single-serving cookies feature a perfect balance of tangy pineapple, buttery cookie dough, and soft, chewy texture crowned with optional maraschino cherries. Perfect for parties, snacks, or gifting, this simple recipe yields irresistibly moist and flavorful cookies.

Ingredients

Scale

Dry Ingredients

  • 1 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt

Wet Ingredients

  • 1/2 cup unsalted butter, softened
  • 1/2 cup brown sugar, packed
  • 1/4 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract

Fruit

  • 1/2 cup crushed pineapple, well drained
  • 1/4 cup chopped maraschino cherries (optional)

Instructions

  1. Prep the Ingredients: Drain the crushed pineapple thoroughly to remove excess moisture. Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone mat.
  2. Mix Dry Ingredients: In a medium bowl, whisk together the all-purpose flour, baking powder, and salt to evenly distribute the leavening and seasoning.
  3. Cream Butter and Sugars: Using a hand or stand mixer, beat the softened unsalted butter with the brown sugar and granulated sugar until the mixture is light, fluffy, and creamy, helping to develop the signature caramel flavor.
  4. Add Egg and Vanilla: Beat in the egg and vanilla extract until fully incorporated, adding moisture and richness to the dough.
  5. Combine Wet and Dry Ingredients: Gradually mix in the dry ingredients without overworking. Gently fold in the well-drained crushed pineapple and optional chopped maraschino cherries for bursts of tropical flavor.
  6. Shape and Bake: Drop spoonfuls of dough onto the prepared baking sheet about 2 inches apart. Bake for 12 to 15 minutes, until edges are golden and centers appear set but still soft.
  7. Cool and Enjoy: Let the cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely, allowing the sugars to set and preventing sticking.

Notes

  • Drain pineapple thoroughly to avoid soggy dough and poor browning.
  • Use room temperature butter and egg for better mixing and dough consistency.
  • Mix just until combined to keep cookies tender, avoiding toughness.
  • Space cookies evenly on the baking sheet for uniform spreading and baking.
  • Optionally chill the dough for 30 minutes before baking to enhance flavor and control spreading.

Nutrition

Keywords: pineapple cookies, upside down cookies, tropical cookies, caramel cookies, easy cookies, sweet treats