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Pineapple Cherry Upside Down Cookies

Soft, tender sugar cookies meet a luscious, fruity topping in these mini pineapple upside-down cookie treats. Each bite-sized dessert combines golden-baked cookie dough with a layer of sweet pineapple and vibrant maraschino cherry, perfect for festive gatherings or a tropical-inspired indulgence.
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Course: Dessert
Cuisine: American
Keyword: Pineapple Cherry Upside Down Cookies
Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes
Servings: 6

Ingredients

For the fruit topping:

  • 12 maraschino cherries thoroughly drained
  • 6 circular pineapple slices halved (fresh or from a can)
  • 4 tablespoons melted unsalted butter
  • 8 tablespoons light brown sugar firmly packed

For the cookie dough:

  • 1/2 teaspoon baking powder
  • 1/2 cup pineapple juice preferably from the canned fruit or freshly squeezed
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 cup granulated sugar
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon fine salt
  • 2 sticks 1 cup unsalted butter, softened to room temperature
  • 2 1/4 cups plain all-purpose flour

Instructions

  • Preheat the oven to 350°F (175°C) and lightly coat two 12-cup muffin pans with nonstick spray or line with paper cups.
  • For the topping, stir the melted butter together with the brown sugar in a small bowl until well blended. Spoon 1 teaspoon of the sugar-butter mixture into the base of each muffin cup.
  • Place a halved pineapple ring over the sugar in each cup, then nestle a maraschino cherry in the center of the ring.
  • To prepare the dough, beat the softened butter and granulated sugar in a large mixing bowl until the texture is airy and light, about 2 minutes.
  • Incorporate the egg, vanilla, and pineapple juice into the creamed mixture, mixing just until combined.
  • In a separate bowl, whisk together the flour, baking powder, baking soda, and salt until evenly distributed.
  • Gradually incorporate the dry mixture into the wet ingredients, stirring until a cohesive and soft dough develops.
  • Form the dough into balls roughly 1 1/2 inches in diameter. Lightly press each ball into a disc and set it atop the pineapple in the muffin tins, applying gentle pressure.
  • Bake for 11 to 13 minutes, or until the edges of the cookies begin to turn golden.
  • Once removed from the oven, allow the cookies to cool in the tins for 5 minutes. Then, carefully invert the pans over a wire rack or baking sheet so the fruit layer is on top.
  • Let the cookies cool completely before serving to ensure the topping is set and stable.
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