Description

Pineapple Upside Down Sugar Cookies are a creative and delicious twist on the classic pineapple upside-down cake, turned into soft, buttery sugar cookies topped with caramelized pineapple and a maraschino cherry. These cookies offer a perfect balance of sweet fruitiness and rich cookie texture, making them ideal for parties, gatherings, or as a special treat at home.

Ingredients

Scale

For the Cookies:

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

For the Pineapple Topping:

1 cup fresh pineapple, diced (or canned pineapple, drained)
1/4 cup brown sugar, packed
2 tablespoons unsalted butter
Maraschino cherries (for garnish)

Instructions

Prepare the Pineapple Topping: In a small saucepan over medium heat, melt the 2 tablespoons of butter. Add diced pineapple and brown sugar, stirring to combine. Cook for 3-5 minutes until pineapple softens and the mixture bubbles. Remove from heat and let cool slightly.
Prepare the Cookie Dough: Preheat 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 brown sugar until light and fluffy. Beat in eggs one at a time, then add vanilla extract, mixing well. In a separate bowl, whisk flour, baking soda, baking powder, and salt. Gradually add dry ingredients to wet mixture, stirring until just combined.
Assemble and Bake the Cookies: Using a cookie scoop or tablespoon, drop dough onto prepared baking sheets about 2 inches apart. Make a small indentation in the center of each dough mound and spoon pineapple topping into it. Top each cookie with a maraschino cherry. Bake for 10-12 minutes until edges are lightly golden and centers set. Cookies may appear slightly underbaked but will firm as they cool.
Cool and Serve: Remove cookies from oven and cool on baking sheet for 5 minutes. Transfer to a wire rack to cool completely. Serve warm or at room temperature and enjoy the flavors of pineapple upside-down cake in cookie form!

Notes

You can substitute fresh pineapple with canned pineapple; just ensure it is well drained.
Cookies freeze well once fully cooled; store in an airtight container or freezer bag for up to 2 months.
For a tropical twist, add shredded coconut to the cookie dough.
Try substituting pineapple with peaches or cherries for flavor variations.
To enhance sweetness, drizzle cooled cookies with a glaze made from powdered sugar and pineapple juice.
Store leftover cookies in an airtight container at room temperature for up to 3 days.

Prep Time: 20 minutes
Cook Time: 10-12 minutes
Category: Dessert
Method: Baking
Cuisine: American

Keywords: pineapple upside down cookies, sugar cookies with pineapple, caramelized pineapple cookies, fruit topped cookies, pineapple cherry cookies, holiday cookie recipe