Description

These easy pineapple upside down sugar cookies feature a buttery sugar cookie base topped with caramelized pineapple and brown sugar, delivering a tropical twist with minimal effort and under 30 minutes total time.

Ingredients

Scale

2 ½ cups (310g) all-purpose flour
1 teaspoon baking powder
½ teaspoon salt
¾ cup (170g) unsalted butter, softened
1 cup (200g) granulated sugar
1 large egg
1 ½ teaspoons vanilla extract
1 cup (about 250g) canned pineapple rings or chunks, drained
½ cup (100g) packed dark brown sugar
2 tablespoons (28g) butter, melted (for topping)

Instructions

Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat.
In a small bowl, mix the packed brown sugar with melted butter until it resembles wet sand. Spread evenly over the lined baking sheet in a thin layer.
Drain pineapple well. If using rings, cut each ring into quarters. Arrange pineapple pieces evenly over the brown sugar mixture, pressing gently so they stick but don’t sink.
In a large bowl, whisk together flour, baking powder, and salt.
In a separate bowl, beat softened butter and granulated sugar with an electric mixer until light and fluffy, about 2-3 minutes.
Add egg and vanilla extract to the butter mixture and mix until combined.
Slowly add dry ingredients to the wet ingredients, mixing just until a soft dough forms. Do not overmix.
Using a spoon or cookie scoop, drop tablespoon-sized balls of dough evenly over the pineapple and brown sugar layer. Some pineapple may be covered, which is expected.
Bake for 12–15 minutes until cookie tops start to turn golden and edges look set.
Let cookies cool on the baking sheet for about 10 minutes to allow caramel to set.
Carefully slide the parchment paper onto a cooling rack and gently peel the cookies off, revealing the caramelized pineapple topping.
Serve warm or at room temperature, optionally with vanilla ice cream or whipped cream.

Notes

Drain pineapple thoroughly to avoid soggy topping. Use dark brown sugar for best caramel flavor. Let cookies cool on the baking sheet before flipping to prevent caramel from running. Softened butter is key for proper creaming and cookie texture. Use parchment or silicone mat to prevent sticking.

Prep Time: 17 minutes
Cook Time: 15 minutes
Category: Dessert
Cuisine: American

Nutrition

Serving Size: 1 cookie
Calories: 140
Sugar: 12
Sodium: 90
Fat: 6
Saturated Fat: 3.5
Carbohydrates: 22
Fiber: 0.5
Protein: 1.5

Keywords: pineapple upside down cookies, sugar cookies, caramelized topping, quick dessert, tropical cookies, easy cookies, pineapple dessert