Christmas Pineapple Upside-Down Sugar Cookies
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The holiday season is the perfect time to bring joy and sweetness to your kitchen, and what better way than with Christmas Pineapple Upside-Down Sugar Cookies? These delightful treats combine the tropical flavor of pineapple with the festive cheer of maraschino cherries, making them an excellent choice for holiday gatherings or cozy nights at home. They’re not only simple to make but also customizable for all your family’s tastes.
Recipe Information
Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes
Servings: 24
Difficulty Level: Easy
Nutrition Information (per serving)
Calories: 150
Protein: 1.5 grams
Carbohydrates: 22 grams
Fat: 6 grams
Fiber: 0.5 grams
Sugar: 10 grams
Sodium: 80 mg
Why Make Christmas Pineapple Upside-Down Sugar Cookies
These Christmas Pineapple Upside-Down Sugar Cookies are a fantastic way to liven up your holiday dessert table. With the delicious combination of flavors and the beautiful presentation, these cookies leave a lasting impression on friends and family. Plus, they offer a delightful balance of sweetness and freshness, making them a healthier alternative to traditional holiday desserts packed with heavy flavors.
How to Make Christmas Pineapple Upside-Down Sugar Cookies Step by Step
Ingredients
1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 1/2 cups all-purpose flour
1 teaspoon baking powder
1/2 teaspoon salt
1/2 cup crushed pineapple, drained
1/4 cup maraschino cherries, halved
2 tablespoons brown sugar
1 teaspoon ground cinnamon
Directions
- Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
- In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
- Beat in the egg and vanilla extract until well combined.
- In a separate bowl, whisk together the flour, baking powder, and salt.
- Gradually add the dry ingredients to the wet ingredients and mix until a dough forms.
- In a small bowl, combine the brown sugar and ground cinnamon.
- Roll dough into 1-inch balls. Flatten each ball slightly and sprinkle a pinch of the cinnamon-sugar mixture on top.
- Place a small spoonful of drained crushed pineapple on each cookie, then top with a half maraschino cherry, pressing gently to adhere.
- Arrange cookies on the prepared baking sheet about 2 inches apart.
- Bake for 12-15 minutes, or until the edges are lightly golden.
- Remove from oven and let cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

How to Serve Christmas Pineapple Upside-Down Sugar Cookies
These festive cookies are perfect on their own but can be enhanced with a scoop of vanilla ice cream or a dollop of whipped cream. For an extra touch, serve with a side of fresh fruit salad or warm gingerbread. They also make a lovely pairing with hot cocoa or spiced holiday tea.
How to Store Christmas Pineapple Upside-Down Sugar Cookies
Store your Christmas Pineapple Upside-Down Sugar Cookies in an airtight container at room temperature for up to a week. For longer storage, you can freeze the cookies in a freezer-safe container or zip-top bag for up to three months. If you’re reheating from frozen, simply place them in a preheated oven at 300°F (150°C) for about 5-10 minutes until warmed through.
Expert Tips for Cooking Christmas Pineapple Upside-Down Sugar Cookies
- Make sure your butter is softened to room temperature for easy creaming with sugar.
- Drain the crushed pineapple thoroughly to prevent excess moisture in the dough.
- Don’t skip the cinnamon-sugar topping; it adds a delightful flavor!
- If you prefer a chewy cookie, slightly underbake them by a minute or two.
- For a fun twist, experiment with adding different flavored extracts, like almond or coconut.
Delicious Variations of Christmas Pineapple Upside-Down Sugar Cookies
- Add chopped pecans or walnuts to the dough for a nutty crunch.
- Swap out the maraschino cherries for candied cherries for a more authentic upside-down cake flavor.
- Use brown sugar for a deeper flavor in the dough, complementing the pineapple perfectly.
Frequently Asked Questions about Christmas Pineapple Upside-Down Sugar Cookies
What is the best way to tell when the cookies are done baking?
The cookies are done when the edges appear lightly golden, and the centers are still soft.
Can I use fresh pineapple instead of canned?
Yes, just ensure the fresh pineapple is well-drained and chopped finely to avoid excess moisture.
How can I enhance the flavor of my cookies?
Incorporating a teaspoon of coconut extract along with the vanilla can give these cookies an extra tropical twist.
Conclusion
Don’t miss out on the chance to make Christmas Pineapple Upside-Down Sugar Cookies this holiday season. With their unique flavors and gorgeous presentation, they are sure to impress everyone at your gatherings. Plus, they’re a breeze to whip up, making them a must-try!







