If you are on the lookout for a delightful twist to your cookie routine, this Pineapple Upside-Down Sugar Cookies Recipe is about to become your new obsession. These cookies beautifully marry the tropical sweetness of pineapple with the classic charm of sugar cookies, topped with maraschino cherries and a sprinkle of brown sugar for that irresistible caramelized finish. Each bite offers a soft, buttery texture with bursts of juicy pineapple and a subtle hint of vanilla, making them an utterly charming treat for any occasion. Trust me, once you try this recipe, it will be a go-to in your baking rotation!
Ingredients You’ll Need
The magic behind this Pineapple Upside-Down Sugar Cookies Recipe lies in its simple yet thoughtfully chosen ingredients. Each element not only ensures the perfect cookie texture but also layers flavors that delight your palate with every bite.
- 1 cup unsalted butter, softened: Provides rich creaminess and the perfect texture when creamed with sugar.
- 1 cup granulated sugar: Sweetens the cookies and helps achieve a tender crumb.
- 1 egg: Binds ingredients and adds moisture for softness.
- 1 teaspoon vanilla extract: Adds aromatic warmth that elevates the overall flavor.
- 2 1/2 cups all-purpose flour: The structural base of the cookie; ensures a delightful chewy bite.
- 1/2 teaspoon baking powder: Gives a little lift to keep cookies light and soft.
- 1/4 teaspoon salt: Balances sweetness and enhances flavors.
- 1/2 cup crushed pineapple, drained: Brings juicy tropical brightness without making dough soggy.
- Maraschino cherries, halved: Acts as a vibrant, sweet topping and adds classic pineapple upside-down cake charm.
- Brown sugar for sprinkling: Caramelizes slightly in the oven for a beautiful finish and extra sweetness.
How to Make Pineapple Upside-Down Sugar Cookies Recipe
Step 1: Preheat and Prepare
Start by heating your oven to 350°F (175°C). Line a baking sheet with parchment paper to prevent sticking and make clean-up a breeze. This simple preparation will ensure your cookies bake evenly and come off the sheet perfectly.
Step 2: Cream Butter and Sugar
In a large mixing bowl, beat together the softened unsalted butter and granulated sugar until the mixture becomes light and fluffy. This creaming process is crucial as it incorporates air, giving your cookies a tender, melt-in-your-mouth quality.
Step 3: Add Egg and Vanilla
Mix in the egg and vanilla extract until fully combined. This step infuses the dough with moisture and rich flavor, setting the foundation for those beautifully fragrant cookies.
Step 4: Combine Dry Ingredients
In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add these dry ingredients to the wet mixture, stirring until just combined. Be careful not to overmix—this keeps your cookies soft and tender.
Step 5: Fold in Pineapple
Gently fold in the drained crushed pineapple. This little burst of tropical flavor will give your cookies a unique twist and moisture without weighing them down or making the dough soggy.
Step 6: Shape and Top
Scoop tablespoon-sized balls of dough onto your prepared baking sheet, spacing them a couple of inches apart to allow spreading. Press a halved maraschino cherry into the center of each cookie, then sprinkle a pinch of brown sugar on top. This step is where your cookies start looking as gorgeous as they will taste.
Step 7: Bake and Cool
Bake for 10 to 12 minutes or until the edges are just lightly golden. Let the cookies cool on the baking sheet for a few minutes—it helps them set up—then transfer to a wire rack to cool completely. This cooling time lets their flavors fully develop and the texture perfect.
How to Serve Pineapple Upside-Down Sugar Cookies Recipe
Garnishes
To add an extra touch of flair, sprinkle a tiny amount of toasted coconut flakes or finely chopped pecans over the cookies just before serving. These garnishes complement the tropical notes and add inviting texture contrast.
Side Dishes
These cookies pair beautifully with a scoop of vanilla ice cream or a dollop of whipped cream, turning a simple cookie into a scrumptious dessert. A refreshing glass of cold milk or pineapple-infused iced tea also complements their sweetness perfectly.
Creative Ways to Present
For parties or gifts, arrange these cookies on a bright platter lined with fresh pineapple leaves or edible flowers to echo the tropical theme. You can even sandwich two cookies with pineapple cream cheese frosting for a show-stopping twist!
Make Ahead and Storage
Storing Leftovers
Keep any leftover Pineapple Upside-Down Sugar Cookies Recipe treats in an airtight container at room temperature for up to four days. This preserves their soft texture and keeps the pineapple flavor fresh and vibrant.
Freezing
If you want to bake ahead or save some for later, these cookies freeze well. Place them in an airtight container or freezer bag with parchment between layers, and freeze for up to three months. Thaw at room temperature when ready to enjoy.
Reheating
To bring back that fresh-baked warmth, pop your cookies briefly in a preheated oven at 300°F for 5 minutes or microwave for about 10 seconds. This will revive their softness and enhance the pineapple aroma.
FAQs
Can I use fresh pineapple instead of canned crushed pineapple?
Absolutely! Just make sure to finely crush the pineapple and drain it well to avoid extra moisture that could affect cookie texture.
What if I don’t have maraschino cherries?
You can substitute with small fresh cherries or even a small piece of candied cherry. The effect won’t be quite the same visually but will still add that sweet fruit pop.
Are these cookies chewy or crispy?
They are delightfully soft and slightly chewy, thanks to the buttery dough and juicy pineapple gently folded in.
Can I make these cookies gluten-free?
Yes! Swap the all-purpose flour for a gluten-free blend suitable for baking, and keep an eye on texture as some blends absorb moisture differently.
How do I prevent the cookies from spreading too much?
Make sure your butter is softened but not melted and chill the dough for 30 minutes before baking if your kitchen is warm. This helps the cookies hold their shape better.
Final Thoughts
I truly hope you give this Pineapple Upside-Down Sugar Cookies Recipe a whirl, because it’s one of those rare treats that feels both nostalgic and refreshingly new. The way the pineapple and cherry top bring a sunny burst of flavor to soft, buttery sugar cookies is utterly irresistible. Whether you’re baking for friends, family, or just yourself, these cookies will definitely bring a smile and maybe even start a new tradition in your kitchen. Happy baking!
Print
Pineapple Upside-Down Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 12 minutes
- Total Time: 27 minutes
- Yield: 24 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Pineapple Upside Sugar Cookies combine the tropical sweetness of crushed pineapple and maraschino cherries with the comforting texture of classic sugar cookies. With a buttery base enhanced by vanilla and a touch of brown sugar on top, these cookies are a delightful treat perfect for any occasion.
Ingredients
Cookies
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 egg
- 1 teaspoon vanilla extract
- 2 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
- 1/2 cup crushed pineapple, drained
Toppings
- Maraschino cherries, halved
- Brown sugar for sprinkling
Instructions
- Preheat Oven: Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper to ensure the cookies do not stick and bake evenly.
- Cream Butter and Sugar: In a mixing bowl, cream together the softened unsalted butter and granulated sugar until the mixture is light and fluffy, which helps create a tender cookie texture.
- Add Egg and Vanilla: Mix in the egg and vanilla extract thoroughly to incorporate moisture and flavor into the dough.
- Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt to evenly distribute the leavening agent and seasoning.
- Mix Dry and Wet Ingredients: Gradually add the flour mixture to the wet ingredients, stirring until just combined to avoid overworking the dough.
- Fold in Pineapple: Gently fold in the drained crushed pineapple to incorporate tropical flavor and moisture without breaking the dough down.
- Form Cookies: Scoop tablespoon-sized balls of dough onto the prepared baking sheet, spacing them adequately to allow for spreading during baking.
- Add Cherry and Sugar Topping: Press a halved maraschino cherry into the center of each cookie and sprinkle a pinch of brown sugar on top for extra sweetness and a slight caramelized crunch.
- Bake: Bake the cookies in the preheated oven for 10-12 minutes or until the edges turn lightly golden, indicating they are perfectly baked.
- Cool: Allow cookies to cool on the baking sheet for a few minutes to firm up before transferring them to a wire rack to cool completely, ensuring the perfect texture.
Notes
- Make sure to drain the crushed pineapple well to prevent soggy dough.
- If you prefer a more pronounced pineapple flavor, add a teaspoon of pineapple juice to the dough but reduce the egg slightly to maintain consistency.
- For a festive presentation, you can use cherries soaked in pineapple juice instead of maraschino cherries.
- Store cookies in an airtight container at room temperature for up to 4 days.
- For a softer cookie, slightly underbake by a minute and allow to cool on the baking sheet.
