Pineapple Upside Down Sugar Cookies are a fun and delicious take on the classic pineapple upside-down cake, but in cookie form! With a soft, buttery sugar cookie base topped with sweet caramelized pineapple and a maraschino cherry, these cookies offer the perfect combination of flavors and textures. The bright and tropical taste of pineapple adds a refreshing contrast to the sweetness of the cookie, making them an ideal treat for any occasion—whether for a summer gathering, a holiday cookie exchange, or a special dessert after dinner.

Ingredients:

For the sugar cookie dough:

• 1 1/2 cups all-purpose flour
• 1/2 teaspoon baking soda
• 1/4 teaspoon salt
• 1/2 cup unsalted butter, softened
• 3/4 cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 1 tablespoon milk

For the topping:

• 1 can (8 oz) pineapple rings, drained and cut into small pieces (or fresh pineapple)
• 1/4 cup brown sugar, packed
• 1 tablespoon unsalted butter, melted
• 10-12 maraschino cherries, halved

Directions:

For the sugar cookie dough:

1. Preheat the oven: Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat.
2. Mix dry ingredients: In a medium bowl, whisk together the flour, baking soda, and salt. Set aside.
3. Cream butter and sugar: In a large mixing bowl, beat the softened butter and granulated sugar together until light and fluffy, about 2-3 minutes.
4. Add egg and vanilla: Beat in the egg and vanilla extract until fully incorporated. Then, add the milk and mix well.
5. Combine the dough: Gradually add the dry ingredients to the wet ingredients, mixing until just combined.

For the topping:

1. Prepare the pineapple topping: In a small bowl, combine the brown sugar and melted butter. Stir in the chopped pineapple and mix until well-coated.
2. Form the cookies: Scoop tablespoon-sized portions of the sugar cookie dough and roll them into balls. Place them on the prepared baking sheet, spaced about 2 inches apart.
3. Top with pineapple and cherries: Gently press down each cookie dough ball to flatten it slightly. Spoon a small amount of the pineapple topping onto each cookie. Press a maraschino cherry half into the center of the pineapple topping.
4. Bake the cookies: Bake for 10-12 minutes, or until the edges of the cookies are golden brown. The cookies will spread slightly, creating a round shape with a pineapple topping.
5. Cool and serve: Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.

Notes:

• Pineapple Variations: You can use fresh pineapple or canned pineapple for the topping. Be sure to drain the pineapple thoroughly to prevent excess moisture in the cookies.
• Cookie Size: If you prefer smaller cookies, you can reduce the portion size of the dough. Just keep an eye on the baking time to ensure they don’t overbake.
• Storage: Store the cookies in an airtight container at room temperature for up to 3 days. For longer storage, you can freeze the cookies for up to 2 months.

Conclusion:

Pineapple Upside Down Sugar Cookies are a tropical and fun twist on a classic dessert. With their buttery sugar cookie base, sweet caramelized pineapple, and tangy maraschino cherry on top, these cookies are sure to be a crowd favorite. Perfect for a holiday treat, summer party, or just a delicious snack, these cookies bring the flavors of a pineapple upside-down cake into a bite-sized delight. Easy to make and full of flavor, these cookies are bound to become a new favorite in your baking rotation.