Pineapple Upside Down Sugar Cookies – A Tropical Twist on a Classic
Pineapple Upside Down Sugar Cookies – a delightful twist on the classic pineapple upside down cake! Soft, buttery sugar cookies topped with caramelized pineapple rings and a sprinkle of sugar. These easy drop cookies bring all the nostalgic flavor in a perfectly portable, bite-sized form.
- Prep Time: 15 minutes
- Cook Time: 13 minutes
- Total Time: 28 minutes
- Yield: 12-15 cookies
- Category: Dessert, Cookies
- Method: Bake
- Cuisine: American
- Diet: Vegetarian
Ingredients
- 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 additional sugar for sprinkling
- Equipment:
- mixing bowl
- baking trays
- Parchment Paper
- whisk
- Cookie Scoop
- wire rack
Instructions
- Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper.
- Cream the softened unsalted butter and granulated sugar together until light and fluffy, about 2-3 minutes.
- Add the large egg and vanilla extract, beating well until combined.
- Whisk together the all-purpose flour, baking soda, and salt in a separate bowl, then gradually mix into the wet mixture until a soft dough forms.
- Scoop 2 tablespoons of dough for each cookie and place on the prepared trays, leaving space between each.
- Press a pineapple ring gently into each dough mound, flattening slightly.
- Sprinkle additional sugar generously on top of the pineapple rings.
- Bake for 11-13 minutes, or until edges are golden and centers are set.
- Cool the cookies on the tray for a few minutes before transferring to a wire rack for complete cooling.
Notes
- Drain pineapple rings very well and pat dry with paper towels to prevent excess moisture in the cookies.
- For smaller cookies, use 1 tablespoon of dough and pineapple tidbits instead of rings.
- Add a maraschino cherry in the center of each pineapple ring for a classic pineapple upside down look.
- Store in an airtight container at room temperature for up to 5 days.
- These cookies freeze beautifully for up to 3 months – thaw at room temperature before serving.
- For an extra buttery flavor, brush the pineapple rings with melted butter before adding the sugar sprinkle.
- Substitute fresh pineapple slices for canned – sauté briefly to reduce moisture.
- Make mini versions using a mini cookie scoop and halved pineapple rings or tidbits.