Pineapple Upside Down Sugar Cookies are a delightful twist on the classic pineapple upside-down cake, transforming it into a fun and portable cookie form. These cookies feature a soft, buttery sugar cookie base topped with sweet caramelized pineapple and a cherry, making them perfect for any gathering or as a sweet treat at home!

Ingredients

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)

Timing

Making Pineapple Upside Down Sugar Cookies takes about 20 minutes for preparation and 10-12 minutes for baking.

Instructions

Step 1: Prepare the Pineapple Topping

1. Melt Butter: In a small saucepan over medium heat, melt the 2 tablespoons of butter. Add the diced pineapple and brown sugar, stirring to combine.
2. Cook: Cook for 3-5 minutes until the pineapple is softened and the mixture is bubbly. Remove from heat and let cool slightly.

Step 2: Prepare the Cookie Dough

1. Preheat Oven: Preheat your oven to 350°F (175°C). Line baking sheets with parchment paper.
2. Cream Butter and Sugars: In a large mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
3. Add Eggs and Vanilla: Beat in the eggs one at a time, followed by the vanilla extract, mixing until well combined.
4. Mix Dry Ingredients: In another bowl, whisk together the flour, baking soda, baking powder, and salt.
5. Combine Mixtures: Gradually add the dry ingredients to the wet ingredients, mixing until just combined.

Step 3: Assemble and Bake the Cookies

1. Scoop Dough: Use a cookie scoop or tablespoon to drop dough onto the prepared baking sheets, spacing them about 2 inches apart.
2. Add Pineapple Topping: Make a small indentation in the center of each cookie dough mound and spoon a small amount of the pineapple mixture into the indentation. Top each with a maraschino cherry.
3. Bake: Bake in the preheated oven for 10-12 minutes, or until the edges are lightly golden and the centers are set. The cookies may look slightly underbaked but will firm up as they cool.

Step 4: Cool and Serve

1. Cool: Remove the cookies from the oven and let them cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.
2. Enjoy: Serve warm or at room temperature, and enjoy the delightful flavors of pineapple upside-down cake in cookie form!

Nutritional Information

Here’s a quick overview of the nutritional content of Pineapple Upside Down Sugar Cookies (per cookie, based on 24 cookies):

Nutrient	Amount per Cookie
Calories	160
Protein	2g
Fat	7g
Carbohydrates	24g
Sugar	10g

Tips for Customization

• Add Coconut: Incorporate shredded coconut into the cookie dough for a tropical twist.
• Use Other Fruits: Substitute pineapple with other fruits like peaches or cherries for different flavor variations.
• Glaze Option: Drizzle a simple glaze made of powdered sugar and pineapple juice over the cooled cookies for extra sweetness.

Storage Instructions

Store any 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.

Conclusion

Pineapple Upside Down Sugar Cookies are a fun and delicious twist on a classic dessert. Soft, buttery, and topped with sweet caramelized pineapple and cherries, these cookies are sure to be a hit at any gathering!

FAQs

Can I use canned pineapple?

Yes, you can use canned pineapple. Just make sure to drain it well before using.

Are these cookies suitable for freezing?

Yes, these cookies freeze well. Just ensure they are completely cooled before storing them in an airtight container or freezer bag.