Christmas Pineapple Upside Down Sugar Cookies: A Festive Twist on a Classic

Ready to bake your way into the holiday spirit? These Christmas Pineapple Upside Down Sugar Cookies combine the nostalgic flavors of pineapple upside-down cake with the convenience and fun of cookies. Perfect for holiday parties, cookie exchanges, or just a cozy night in by the Christmas tree.

Why This Recipe Works

  • The combination of buttery sugar cookie base with caramelized pineapple and cherries offers a delightful contrast of textures and flavors.
  • Using pre-made sugar cookie dough saves time without sacrificing taste, making this recipe accessible for bakers of all levels.
  • The upside-down technique ensures each cookie is a mini masterpiece, with the pineapple and cherry topping perfectly displayed.
  • These cookies are as fun to make as they are to eat, offering a creative twist on traditional holiday baking.

Ingredients

  • 1 package (16.5 oz) pre-made sugar cookie dough
  • 1/2 cup unsalted butter, melted
  • 1 cup packed brown sugar
  • 1 can (20 oz) pineapple slices, drained and cut into small pieces
  • 1/2 cup maraschino cherries, drained and halved

Equipment Needed

  • Muffin tin
  • Mixing bowls
  • Measuring cups and spoons
  • Spoon or cookie scoop

Instructions

Christmas Pineapple Upside Down Sugar Cookies

Preheat and Prepare

Preheat your oven to 350°F. In a small bowl, mix the melted butter and brown sugar until well combined. Spoon this mixture evenly into the bottom of each cup in your muffin tin. Tip: A small cookie scoop can help distribute the mixture evenly.

Add the Toppings

Place a piece of pineapple and a cherry half in the center of each muffin cup on top of the butter and sugar mixture. The pineapple and cherry will caramelize as the cookies bake, creating a delicious topping.

Prepare the Cookie Dough

Roll the sugar cookie dough into small balls, about 1 inch in diameter. Place each ball on top of the pineapple and cherry in the muffin cups. Tip: If the dough is too sticky, lightly flour your hands to make rolling easier.

Bake to Perfection

Bake in the preheated oven for 12-15 minutes, or until the edges of the cookies are golden brown. The sugar and butter mixture will bubble up around the cookies, creating a caramelized effect.

Flip and Serve

Allow the cookies to cool in the muffin tin for about 5 minutes. Then, carefully flip the tin over onto a baking sheet or parchment paper to release the cookies. Tip: Use a butter knife to loosen any cookies that stick to the tin.

Tips and Tricks

For an extra festive touch, sprinkle a little cinnamon or nutmeg into the butter and sugar mixture before adding the pineapple and cherries. If you’re using fresh pineapple, make sure to pat the pieces dry to prevent excess moisture. To ensure even baking, rotate the muffin tin halfway through the baking time. For a more intense caramel flavor, let the butter and sugar mixture sit for a few minutes before adding the toppings.

Recipe Variations

  • Try using different fruits, such as peaches or apricots, for a twist on the traditional pineapple topping.
  • Add a sprinkle of shredded coconut to the butter and sugar mixture for a tropical flavor.
  • For a richer cookie, substitute the sugar cookie dough with shortbread cookie dough.
  • Drizzle the finished cookies with a little melted chocolate or caramel sauce for extra decadence.

Frequently Asked Questions

Can I make these cookies ahead of time?

Yes, you can prepare the muffin tins with the butter, sugar, and toppings a day in advance. Cover them with plastic wrap and store in the refrigerator until you’re ready to add the cookie dough and bake.

How do I store leftover cookies?

Store the cooled cookies in an airtight container at room temperature for up to 3 days. For longer storage, you can freeze the cookies for up to a month.

Can I use fresh pineapple instead of canned?

Absolutely! Just make sure to cut the pineapple into small, uniform pieces and pat them dry to remove excess moisture, which can affect the texture of the cookies.

Summary

These Christmas Pineapple Upside Down Sugar Cookies are a festive and fun twist on traditional holiday baking. Easy to make and even easier to eat, they’re sure to become a new holiday favorite.

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