Dessert

Irresistible Pineapple Upside Down Sugar Cookies Recipe

Byanna orden November 28, 2025November 28, 2025

Introduction

Pineapple Upside Down Sugar Cookies offer a delightful twist on the classic pineapple upside-down cake by turning it into a fun, portable treat. These soft, buttery sugar cookies are topped with caramelized pineapple and a cherry, making them perfect for any occasion.

The image shows a close-up of small round cakes, each with three layers: a golden brown crumbly base, a bright yellow ring of pineapple slice in the middle, and a glossy red cherry sitting in a small pool of shiny red jam in the center, all arranged on a white plate placed on a white marbled textured surface. photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 cup unsalted butter, softened
1 cup granulated sugar
1/2 cup brown sugar, packed
2 large eggs
1 teaspoon vanilla extract
2 1/2 cups all-purpose flour
1 teaspoon baking soda
1/2 teaspoon baking powder
1/2 teaspoon salt
1 cup fresh pineapple, diced (or canned pineapple, drained)
1/4 cup brown sugar, packed (for pineapple topping)
2 tablespoons unsalted butter (for pineapple topping)
Maraschino cherries (for garnish)

Instructions

Step 1: Prepare the pineapple topping by melting 2 tablespoons of butter in a small saucepan over medium heat. Add the diced pineapple and 1/4 cup brown sugar, stirring to combine. Cook for 3-5 minutes until the pineapple softens and the mixture bubbles. Remove from heat and let cool slightly.
Step 2: Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper. In a large bowl, cream together the softened butter, granulated sugar, and 1/2 cup brown sugar until light and fluffy. Beat in the eggs one at a time, then add the vanilla extract and mix well.
Step 3: In another bowl, whisk together the flour, baking soda, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
Step 4: Use a cookie scoop or tablespoon to drop dough onto the prepared baking sheets, spacing them about 2 inches apart. Make a small indentation in the center of each mound and spoon a small amount of the pineapple topping into it. Place a maraschino cherry on top of each.
Step 5: Bake for 10-12 minutes, until edges are lightly golden and centers are set. The cookies may appear slightly underbaked but will firm up as they cool.
Step 6: Let the cookies cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely. Serve warm or at room temperature.

Tips & Variations

Add shredded coconut to the cookie dough for a tropical twist.
Substitute pineapple with peaches or cherries for different flavor variations.
Drizzle a simple glaze made from powdered sugar and pineapple juice over cooled cookies for extra sweetness.

Storage

Store leftover cookies in an airtight container at room temperature for up to 3 days. For longer storage, freeze the cookies for up to 2 months. Make sure cookies are completely cooled before freezing. Reheat gently at room temperature or warm briefly in the oven before serving.