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Pineapple Upside-Down Sugar Cookies

Pineapple Upside-Down Sugar Cookies – A Tropical Twist on a Classic

These Pineapple Upside-Down Sugar Cookies bring a fun twist to the classic pineapple upside-down cake, but in cookie form! Each soft sugar cookie is topped with a caramelized pineapple slice and a bright maraschino cherry, making these cookies a delightful and vibrant treat. They’re perfect for parties, summer gatherings, or whenever you want a taste of something tropical. Let’s get into this easy and delicious recipe!

Table of Contents

  1. Ingredients for Pineapple Upside-Down Sugar Cookies
  2. Instructions for Pineapple Upside-Down Sugar Cookies
  3. Tips & Notes
  4. Recipe Variations & Substitutions
  5. Frequently Asked Questions (FAQs)
  6. Conclusion

Ingredients for Pineapple Upside-Down Sugar Cookies

  • 1/2 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1 can pineapple rings, drained (cut into smaller pieces if needed)
  • 1/4 cup light brown sugar
  • 1 tablespoon unsalted butter (for caramelizing)
  • Maraschino cherries, halved

Instructions for Pineapple Upside-Down Sugar Cookies

Step 1: Prepare the Cookie Dough

  • In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, about 2-3 minutes.
  • Beat in the egg and vanilla extract until well combined.
  • In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing just until combined. Cover and chill the dough for at least 30 minutes.

Step 2: Prepare the Pineapple Topping

  • In a skillet over medium heat, melt 1 tablespoon of butter. Add the brown sugar and stir until it begins to melt and combine, about 1-2 minutes.
  • Add the pineapple rings to the skillet and cook for about 2 minutes on each side, until lightly caramelized. Remove from heat and let cool slightly.

Step 3: Assemble the Cookies

  • Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.
  • Scoop about 1 1/2 tablespoons of chilled cookie dough and roll it into a ball. Place it onto the prepared baking sheet and slightly flatten it with your hand.
  • Place a caramelized pineapple piece on top of each flattened cookie dough, pressing it down gently. Add a maraschino cherry half in the center of each pineapple.

Step 4: Bake the Cookies

  • Bake the cookies in the preheated oven for 12-15 minutes, or until the edges are lightly golden.
  • Allow the cookies to cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely.

Tips & Notes

  • Chill the Dough: Chilling the dough helps the cookies keep their shape while baking, so don’t skip this step!
  • Smaller Pineapple Pieces: If the pineapple rings are too large for the cookies, cut them into smaller segments that fit neatly on top of each cookie.
  • Avoid Overbaking: Keep an eye on the cookies and take them out when the edges are just starting to turn golden to keep them soft.

Recipe Variations & Substitutions

  • Coconut Twist: Add 1/4 cup of shredded coconut to the cookie dough for a tropical coconut flavor.
  • Brown Sugar Cookies: Substitute granulated sugar with light brown sugar for a richer, more caramel-like flavor in the cookie base.
  • Glaze: Drizzle the cookies with a simple powdered sugar glaze for an extra layer of sweetness.

Frequently Asked Questions (FAQs)

1. How do I store Pineapple Upside-Down Sugar Cookies?

Store the cookies in an airtight container at room temperature for up to 3 days. For longer storage, refrigerate them for up to 5 days.

2. Can I use fresh pineapple instead of canned?

Yes, you can use fresh pineapple. Just make sure to cut it into small, even pieces, and caramelize it as directed for the best flavor.

3. Can I make the cookie dough ahead of time?

Absolutely! The dough can be made and refrigerated for up to 24 hours before baking. Let it sit at room temperature for a few minutes if it’s too firm to scoop.

4. Can I freeze these cookies?

Yes, you can freeze the baked cookies for up to 2 months. Thaw at room temperature before serving.

These Pineapple Upside-Down Sugar Cookies are a delightful way to bring tropical flavors to your dessert table. The combination of soft sugar cookies with caramelized pineapple and a bright maraschino cherry makes each bite flavorful and fun. Whether it’s for a summer gathering or just a treat at home, these cookies are sure to impress. Give this easy recipe a try and enjoy every sweet, tropical bite!

Happy baking, and enjoy this tasty twist on a classic favorite!