Pineapple Upside Sugar Cookies

 

Experience the classic flavor of pineapple upside-down cake in a delightful, handheld cookie form. Each soft, buttery sugar cookie boasts a sweet and tangy caramelized pineapple top, creating a perfect bite of tropical comfort. Quick to make and irresistibly delicious, these cookies are sure to become a new favorite.

• ⏰ Prep Time: 20 minutes

• ⏰ Bake Time: 12-15 minutes

• 🍽️ Yields: 12-16 cookies

🧂 INGREDIENTS

For the Pineapple Topping:

• 1 fresh pineapple, peeled, cored, and sliced into ½-inch rings (or 1 can of pineapple rings, drained)

• 2 tablespoons unsalted butter, melted

• 2 tablespoons brown sugar

• ¼ teaspoon ground cinnamon (optional)

For the Sugar Cookie Dough:

• 1 cup (2 sticks / 226g) unsalted butter, softened

• 1 cup (200g) granulated sugar

• 1 large egg

• 1 teaspoon pure vanilla extract

• 2¼ cups (280g) all-purpose flour

• 1 teaspoon baking powder

• ¼ teaspoon salt

👩‍🍳 INSTRUCTIONS

1. Preheat and Prepare:

• Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.

2. Create the Pineapple Topping:

• If using fresh pineapple, ensure the rings are patted dry. If using canned, drain well.

• Arrange the pineapple rings on the prepared baking sheet. Brush the top of each ring with melted butter and sprinkle evenly with brown sugar and the optional cinnamon.

3. Make the Cookie Dough:

• In a large bowl, using an electric mixer, cream the softened butter and granulated sugar together until light and fluffy.

• Beat in the egg and vanilla extract until just combined.

• In a separate bowl, whisk together the flour, baking powder, and salt.

• Gradually add the dry ingredients to the wet ingredients, mixing on low speed until a soft dough forms.

4. Assemble the Cookies:

• Scoop about 1½ tablespoons of dough for each cookie. Flatten the dough into a disc slightly smaller than your pineapple ring.

• Gently place a dough disc on top of each prepared pineapple ring, lightly pressing to seal the edges and cover the pineapple.

5. Bake:

• Bake for 12-15 minutes, or until the cookie edges are lightly golden.

• Let the cookies cool on the baking sheet for 5 minutes. They will be soft.

6. Flip and Serve:

• Carefully flip each cookie over so the caramelized pineapple is on top.

• Allow to cool completely on a wire rack. The pineapple topping will be hot.

💡 Pro-Tips & Variations:

• Perfect Pineapple: For easier eating, you can chop the pineapple rings into smaller pieces before topping them with the dough.

• Glaze it Up: For extra sweetness, drizzle the cooled cookies with a simple glaze made from ½ cup powdered sugar and 1-2 teaspoons of milk or pineapple juice.

• Add Some Crunch: Sprinkle toasted coconut or chopped macadamia nuts over the pineapple before adding the dough for a tropical crunch.

• Storage: Store in an airtight container at room temperature for up to 3 days. The pineapple may soften the cookies over time.