Why You’ll Like This Recipe

These cookies capture the best elements of a nostalgic treat, combining buttery softness with a fruity explosion from the pineapple and cherries. They’re not only a breeze to make but also add a cheerful flavor to any holiday gathering. With every bite, you’ll be taken back to the classic flavors of pineapple upside-down cake, making these cookies a must-have for your festive baking list.

Recipe: Christmas Pineapple Upside-Down Sugar Cookies

Ingredients

For the Cookie Dough:

• 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 powder
• 1/4 teaspoon salt

For the Topping:

• 6 maraschino cherries, halved
• 1/4 cup crushed pineapple, drained well
• 2 tablespoons brown sugar

Instructions

Step 1: Prepare the Topping
In a small mixing bowl, combine the drained crushed pineapple and brown sugar, stirring until the pineapple is evenly coated with the sugar. Set this mixture aside, letting the flavors meld while you prepare the cookies.

Step 2: Make the Cookie Dough
Use a mixing bowl to cream together the softened butter and granulated sugar until the mixture is light and fluffy. Next, beat in the egg and vanilla extract, ensuring they are fully incorporated. In another bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually fold the dry ingredients into the wet mixture until you’ve created a smooth, soft dough.

Step 3: Assemble the Cookies
Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper. Roll the dough into 1-inch balls and arrange them on the prepared baking sheet, leaving about 2 inches of space between each. Use your fingers or the back of a spoon to gently flatten each ball.

Step 4: Add the Topping
Spoon a small amount of the pineapple-brown sugar mixture onto each cookie. One at a time, press a halved cherry into the center of the topping.

Step 5: Bake the Cookies
Bake the cookies in the preheated oven for about 10-12 minutes or until the edges turn a light golden brown. Once baked, let them cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely.

Serving and Storage Tips

Serving:
These cookies can be enjoyed fresh from the oven or at room temperature. They make a festive addition to cookie exchanges or a delightful treat to share with loved ones.

Storage:
To keep your cookies fresh, store any leftovers in an airtight container at room temperature for up to 3 days. If you want them to last longer, you can refrigerate them for a week or freeze them for up to a month.

Helpful Notes

• Drain Pineapple Well: It’s important to ensure that the crushed pineapple is well-drained to avoid adding excess moisture that could alter the cookie’s texture.
• Dough Chilling (Optional): For ease of handling, consider chilling the dough for 15-20 minutes before rolling it into balls.
• Extra Festive Touch: Add a sprinkle of red and green sanding sugar to the tops of the cookies for an extra holiday sparkle.

FAQs

Q1: Can I use fresh pineapple instead of canned?
Absolutely! Just make sure to finely chop the fresh pineapple and drain it well to avoid excess moisture impacting the cookie texture.

Q2: Can I use another type of sugar for the topping?
While brown sugar creates a rich caramelized flavor, granulated sugar or even honey can be great substitutes if you prefer.

Q3: Can I make these cookies ahead of time?
Yes, you can prepare the dough a day in advance. Simply refrigerate it and then bake the cookies fresh when you’re ready to enjoy them.

Q4: Can I freeze the cookies?
Yes, for long-term storage, freeze them in a single layer on a baking sheet, then transfer them to an airtight container. Thaw them either in the fridge or at room temperature before serving.

Q5: How do I prevent the topping from sliding off?
Make sure to gently press the topping into the cookie dough and ensure that your pineapple is well-drained to help it adhere during baking.