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Pineapple Upside-Down Cookies

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These Pineapple Upside-Down Cookies are a playful twist on the classic cake, featuring buttery cookie dough topped with caramelized pineapple and cherries. They’re easy to make, perfectly portioned, and bring a burst of tropical flavor to any occasion.

Ingredients

Scale
  • 8–10 pineapple rings or 1 cup pineapple tidbits, drained well (fresh or canned in juice)
  • 12–16 maraschino cherries, halved
  • 1/2 cup (100g) light brown sugar
  • 1/4 cup (56g) unsalted butter, melted
  • 2 cups (260g) all-purpose flour
  • 1 teaspoon (4g) baking powder
  • 1/2 teaspoon (3g) salt
  • 1/2 cup (113g) unsalted butter, softened
  • 3/4 cup (150g) granulated sugar
  • 1 large egg, room temperature
  • 2 tablespoons (30ml) pineapple juice (reserved from can)
  • 1 teaspoon (5ml) pure vanilla extract

Instructions

  1. Preheat oven to 350°F (175°C). Line two baking sheets with parchment paper. Drain pineapple and cherries, then pat them very dry with paper towels.
  2. In a small bowl, mix 1/2 cup light brown sugar with 1/4 cup melted butter until a thick paste forms.
  3. Place about 1 teaspoon of the brown sugar-butter mixture in a mound on each spot where you’ll drop dough (leave 2 inches between cookies).
  4. Press a piece of pineapple (quarter of a ring or 1 tablespoon tidbits) onto each sugar-butter mound. Press half a cherry in the center of each pineapple piece.
  5. In a medium bowl, whisk together flour, baking powder, and salt.
  6. In a large bowl, cream softened butter and granulated sugar with an electric mixer on medium speed until light and fluffy (about 2 minutes).
  7. Beat in egg, pineapple juice, and vanilla extract until smooth (the mixture may look slightly curdled).
  8. Gradually add dry ingredients to wet, mixing on low until just combined. Do not overmix.
  9. Use a medium cookie scoop (about 1.5 tablespoons) to drop dough directly on top of each fruit-topped sugar mound. Gently press down so dough covers the fruit.
  10. Bake for 12-15 minutes, rotating the sheet halfway through, until edges are golden and tops are just set.
  11. Let cookies cool on the sheet for 3-4 minutes. While still warm, use a spatula to flip them upside-down onto a wire rack so the fruit and topping are on top.
  12. Let cool completely so the caramel sets. Enjoy!

Notes

Pat pineapple and cherries very dry to prevent cookies from spreading. For gluten-free, use a 1:1 gluten-free flour blend. For dairy-free, use vegan butter. Chill dough for 10-15 minutes if too sticky. Flip cookies while warm for the best glossy finish.

Nutrition

Keywords: pineapple upside-down cookies, pineapple cookies, easy dessert, retro dessert, fruit cookies, summer cookies, potluck dessert, pineapple upside-down cake cookies

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