Tropical Pineapple Upside Sugar Cookies

Indulge in these delightful Tropical Pineapple Upside Sugar Cookies! Featuring buttery sugar cookie dough topped with juicy pineapple rings, a sweet maraschino cherry center, and a generous sprinkle of toasted coconut, these treats bring a burst of tropical flavor to your dessert table. Perfect for a fun snack or festive gathering, ready in under 45 minutes!

Ingredients

For the Cookies:

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg, room temperature
  • 1 teaspoon vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt

For the Topping:

  • 1 can (20 oz) pineapple slices in juice, drained (reserve 2 tablespoons juice)
  • 24 maraschino cherries, drained and patted dry
  • 1 cup sweetened shredded coconut
  • 1/4 cup brown sugar (for a caramelized touch)

Instructions

Step 1: Preheat and Prep (5 minutes) Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone mats to prevent sticking. Drain the pineapple slices, reserving 2 tablespoons of juice, and pat the slices dry with paper towels to avoid excess moisture. Set aside.

Step 2: Make the Cookie Dough (10 minutes) In a large bowl, use an electric mixer to cream the softened butter and granulated sugar together on medium speed until light and fluffy, about 2-3 minutes. Add the egg and vanilla extract, beating until fully incorporated. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, mixing on low speed until a soft dough forms. If the dough feels too sticky, chill it in the fridge for 15 minutes.

Step 3: Shape the Cookies (10 minutes) Scoop tablespoon-sized portions of dough and roll them into balls. Place them on the prepared baking sheets, spacing them about 2 inches apart. Flatten each ball slightly with your fingers or the bottom of a glass. Press a pineapple ring into the center of each dough ball, gently molding the dough around the edges to secure it. Sprinkle about 1 teaspoon of brown sugar over each pineapple ring for a caramelized flavor, then press a maraschino cherry into the center of each ring. Finish by sprinkling shredded coconut over the top, pressing lightly to adhere.

Step 4: Bake (12-15 minutes) Bake in the preheated oven for 12-15 minutes, or until the edges are lightly golden and the coconut is toasted. The centers should still be soft but set. Rotate the trays halfway through baking for even cooking. Remove from the oven and let the cookies cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely (about 10 minutes). The pineapple will firm up as they cool.

Step 5: Serve and Store (5 minutes) Once cooled, stack the cookies on a plate for that eye-catching presentation from your image. Serve as a tropical treat with tea or coffee. Store in an airtight container at room temperature for up to 5 days, or freeze for up to 2 months (thaw at room temperature before serving).

Serving Suggestions

Pair with a dollop of whipped cream or a scoop of vanilla ice cream for an extra indulgent twist. The reserved pineapple juice can be mixed into a glaze (1 cup powdered sugar + 2 tbsp juice) to drizzle over the cookies for added sweetness.

Tips for Success

  • Pineapple Prep: Ensure the pineapple slices are well-drained to prevent soggy cookies. Use canned rings for uniformity, or cut fresh pineapple into rings if preferred.
  • Cherry Placement: Pat cherries dry to avoid excess liquid bleeding into the dough.
  • Texture Boost: Toast the coconut lightly in a skillet before using for a deeper flavor, but watch closely to avoid burning.
  • Variation: Add a pinch of cinnamon to the dough for a warm spice note.

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