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Pineapple Upside Down Cookies

These Pineapple Upside Down Cookies are bursting with tropical flavor and caramelized sweetness in every chewy bite!
Prep Time20 minutes
Cook Time15 minutes
Total Time35 minutes
Servings: 24 servings

Ingredients

  • 1 cup unsalted butter softened
  • 1 cup brown sugar packed
  • 1 cup granulated sugar
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 3 cups all-purpose flour
  • 1 teaspoon baking soda
  • 0.5 teaspoon salt
  • 1 cup crushed pineapple drained
  • 1 cup chopped cherries maraschino or fresh

Instructions

Step 1: Prep Your Ingredients

  • Begin by draining your crushed pineapple thoroughly to avoid excess moisture in your dough. Chop your cherries into small pieces if they aren't pre-chopped. Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper or silicone baking mats.

Step 2: Cream Butter and Sugars

  • In a large mixing bowl, use an electric mixer to cream the softened butter with both the brown sugar and granulated sugar. Beat until the mixture is light and fluffy, about 3-4 minutes. This step is crucial to create a tender cookie texture.

Step 3: Add Eggs and Vanilla

  • Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract. These wet ingredients help bind the dough and add a depth of flavor that enhances the pineapple and cherry notes.

Step 4: Combine Dry Ingredients

  • In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, mixing on low speed until just combined. Avoid overmixing to keep your cookies tender.

Step 5: Fold in Pineapple and Cherries

  • Gently fold in the drained crushed pineapple and chopped cherries with a spatula. The pineapple adds moisture and a tropical tang, while the cherries provide pops of color and sweetness.

Step 6: Shape and Bake

  • Using a cookie scoop or tablespoon, drop dough balls about 2 inches apart on the prepared baking sheets. Flatten each slightly with the palm of your hand or the bottom of a glass to encourage even baking. Bake for 12-15 minutes, or until the edges are golden and the centers are set.

Step 7: Cool and Enjoy

  • Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely. This helps them set and prevents breakage.

Equipment

  • Electric Mixer
  • Mixing bowls
  • Baking Sheets
  • Parchment paper or silicone baking mats
  • Cookie scoop or tablespoon
  • Wire Rack

Notes

  • Drain crushed pineapple thoroughly to avoid overly wet dough and spreading cookies.
  • Use room temperature butter for proper creaming with sugars.
  • Chill dough for 30 minutes before baking to help control spreading and enhance flavors.
  • Try browning the butter for a deeper caramel flavor reminiscent of traditional upside-down cake.
  • Use fresh cherries when in season for a natural flavor or maraschino cherries for vibrant color and sweetness.