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Pineapple Upside Down Sugar Cookies That Delight Every Bite

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Pineapple Upside Down Sugar Cookies are soft, buttery sugar cookies topped with sweet caramelized pineapple rings. Inspired by the classic cake, these cookies deliver nostalgic tropical flavor in every bite and are perfect for parties, potlucks, or holiday dessert trays.

  • Total Time: 38 minutes
  • Yield: 24 cookies

Ingredients

Scale
  • For the Cookie Base
    • 1 cup unsalted butter, softened
    • 1 cup granulated sugar
    • 1 large egg
    • 1 teaspoon vanilla extract (optional)
    • 2 cups all-purpose flour (or gluten-free blend)
    • 1 teaspoon baking soda
    • 1/2 teaspoon salt
  • For the Topping
    • 1 can canned pineapple rings, well-drained
    • 2 tablespoons granulated sugar, for sprinkling

Instructions

  1. Preheat oven to 350°F (180°C) and line baking trays with parchment paper.
  2. Cream butter and sugar until light and fluffy, about 2–3 minutes.
  3. Add egg and vanilla extract; beat until fully combined.
  4. In a separate bowl, whisk flour, baking soda, and salt. Gradually mix into the wet ingredients to form a soft dough.
  5. Scoop about 2 tablespoons of dough per cookie onto prepared trays, spacing evenly.
  6. Press a pineapple ring gently into each dough mound and flatten slightly.
  7. Sprinkle sugar generously over the pineapple rings.
  8. Bake for 11–13 minutes, until edges are lightly golden and centers are set.
  9. Cool briefly on the tray, then transfer to a wire rack to cool completely.

Notes

  • For extra indulgence, serve warm cookies with vanilla bean ice cream.
  • Pat pineapple rings very dry to prevent excess moisture.
  • Cookies store well in an airtight container for up to 3 days.
  • Author: Emma
  • Prep Time: 15 minutes
  • Cook Time: 13 minutes
  • Category: Desserts
  • Method: Baking
  • Cuisine: American