If you’re looking for a fun twist on a classic favorite, this Pineapple Upside-Down Sugar Cookies Recipe is going to steal your heart and your taste buds. Imagine the perfect balance of buttery, sweet sugar cookie dough hugging a luscious pineapple slice glazed with brown sugar goodness and topped with a bright maraschino cherry—it’s almost like dessert nostalgia wrapped up in a bite-sized treat. From the moment you pull them fresh from the oven, those golden edges and that juicy pineapple center promise a delicious experience that’s both familiar and excitingly new.
Ingredients You’ll Need
Gathering simple, quality ingredients is the secret to making these cookies shine. Each element works together to create tender cookies with caramelized sweetness and a pop of tropical flavor that’s absolutely irresistible.
- Unsalted butter: Provides richness and helps create that tender, melt-in-your-mouth texture.
- Granulated sugar: Balances the buttery base with just the right amount of sweetness.
- Large egg: Binds the dough and adds moisture for soft cookies.
- Vanilla extract: Gives a warm, aromatic background that complements the pineapple perfectly.
- All-purpose flour: The structure builder that keeps the cookies tender yet sturdy.
- Baking powder and baking soda: Work together for the perfect rise and lightness.
- Salt: Enhances all the sweet and buttery flavors.
- Pineapple slices (drained): The star ingredient bringing juicy tropical sweetness and a beautiful look.
- Brown sugar: Melts into a luscious caramel with butter, adding depth and chewy texture.
- Maraschino cherries: Pops of vibrant color and fruity sweetness to crown each cookie.
How to Make Pineapple Upside-Down Sugar Cookies Recipe
Step 1: Prep Your Equipment and Ingredients
Start by preheating your oven to 350°F (175°C) and lining two baking sheets with parchment paper. This ensures your cookies bake evenly and come off the pan cleanly, keeping every detail picture-perfect.
Step 2: Cream Butter and Sugar
In a large mixing bowl, beat the softened unsalted butter with granulated sugar until the mixture turns light and fluffy, about 3 to 4 minutes. This step is crucial because it incorporates air for a soft cookie crumb.
Step 3: Add Egg and Vanilla
Mix in the large egg and pure vanilla extract until everything blends smoothly. These ingredients add moisture and flavor depth, making your cookies irresistible from the first bite.
Step 4: Combine Dry Ingredients
Whisk the all-purpose flour with baking powder, baking soda, and salt in a separate bowl. The combination of leaveners helps your cookies rise gently, while the salt sharpens the sweetness.
Step 5: Mix Dry into Wet
Gradually fold the dry ingredients into the butter and sugar mixture. Stir just until everything is combined to avoid tough cookies — tender is the goal here!
Step 6: Make the Caramel Butter Sauce
In a small saucepan over medium heat, melt ¼ cup unsalted butter with ½ cup packed brown sugar. Stir continuously until the mixture bubbles and smooths into a glossy caramel sauce that will coat the pineapple slices beautifully.
Step 7: Assemble Cookies on Baking Sheets
Spoon about one tablespoon of the caramel butter sauce into the center of each cookie spot on your prepared baking sheets. Top each dollop with a drained pineapple slice, letting the sauce soak into the fruit.
Step 8: Add the Cherry
Position a maraschino cherry right smack in the middle of each pineapple slice. This adds a burst of color and the perfect finishing touch to your cookie masterpiece.
Step 9: Spread the Cookie Dough
Scoop a tablespoon of your cookie dough and gently spread it over each pineapple slice, covering slightly but leaving some fruit visible. This balancing act lets the pineapple and caramel sauce peek through, promising every bite is as eye-catching as it is delicious.
Step 10: Bake to Perfection
Place the trays in your preheated oven and bake for 12 to 15 minutes, until the cookie edges turn a lovely light golden brown. The aroma will be heavenly—like sunshine in your kitchen.
Step 11: Cool and Enjoy
Let the cookies rest on the baking sheets for 5 minutes after coming out of the oven. Then transfer them to a wire rack to cool completely. Cooling helps the cookies set so they maintain their shape while keeping that irresistible tender texture.
How to Serve Pineapple Upside-Down Sugar Cookies Recipe
Garnishes
Enhance these cookies by sprinkling a touch of finely chopped toasted coconut or a light dusting of powdered sugar. Both add delightful texture and a little extra sweetness that pairs perfectly with the tropical vibe.
Side Dishes
Pair these cookies with a scoop of vanilla ice cream or a dollop of whipped cream for an extra indulgent treat. They also go wonderfully alongside a cup of strong coffee or tropical iced tea, creating a truly memorable snack or dessert experience.
Creative Ways to Present
For parties or gifting, arrange the cookies on a rustic wooden board with fresh pineapple wedges and cherries for a vibrant display. You can also stack them in pretty jars layered with strands of raffia and tropical-themed tags that scream summer celebration!
Make Ahead and Storage
Storing Leftovers
Keep any uneaten cookies in an airtight container at room temperature. They stay soft and flavorful for up to 4 days, making them a perfect make-ahead dessert for busy schedules.
Freezing
If you want to save these Pineapple Upside-Down Sugar Cookies Recipe for longer, freeze them in a single layer on a baking sheet before transferring to a freezer-safe bag or container. They last up to 3 months, ready to thaw and enjoy anytime you need a sweet tropical escape.
Reheating
Warm frozen or stored cookies in a 300°F oven for about 5 minutes to refresh that just-baked softness. You can also microwave them for 10-15 seconds, but be careful not to overdo it and dry them out.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple slices work beautifully in this recipe, just make sure they’re cut uniformly and drained or patted dry so the cookie dough doesn’t get soggy.
What if I don’t have maraschino cherries?
No worries! Substitute with glacé cherries, or try small pieces of candied ginger or even a raspberry for a different but equally tasty twist.
Can I make the dough ahead of time?
Yes, the dough can be made up to 24 hours in advance and refrigerated. Just let it sit at room temperature briefly before assembling the cookies to make scooping easier.
How do I prevent the pineapple from making the cookies soggy?
Draining the pineapple slices thoroughly and spooning the caramel sauce just before adding the dough helps create a barrier that keeps the cookies tender without becoming mushy.
Are these cookies gluten-free?
This particular recipe uses all-purpose flour, so it’s not gluten-free. However, you can experiment with gluten-free flour blends to make a similar version, keeping in mind texture changes.
Final Thoughts
These Pineapple Upside-Down Sugar Cookies Recipe offer a delightful way to celebrate fruity flavors and classic cookie comfort in one wonderful bite. They’re easy to whip up, visually stunning, and absolutely delicious, making them a sure-fire hit at any gathering—or just a perfect treat to brighten your day. Trust me, once you try them, they’ll become a favorite you’ll want to bake again and again.
Print
Pineapple Upside-Down Sugar Cookies Recipe
- Total Time: 30 minutes
- Yield: 24 servings 1x
Description
These Pineapple Upside-Down Sugar Cookies combine the classic tropical flavors of pineapple and cherry with a soft, buttery sugar cookie base. Featuring a caramelized brown sugar and butter layer topped with pineapple slices and maraschino cherries, these cookies offer a delightful twist on the traditional upside-down cake, perfect for a sweet, fruity treat.
Ingredients
Cookie Dough
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 ½ cups all-purpose flour
- 1 teaspoon baking powder
- ½ teaspoon baking soda
- ½ teaspoon salt
Topping
- 1 can (8 oz) pineapple slices, drained (reserve juice)
- ¼ cup unsalted butter
- ½ cup brown sugar, packed
- Maraschino cherries (one for each cookie)
Instructions
- Preheat Oven: Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper to prevent sticking and ensure even baking.
- Cream Butter and Sugar: In a mixing bowl, beat the softened butter and granulated sugar together until the mixture is light, fluffy, and well combined, about 3-4 minutes.
- Add Egg and Vanilla: Incorporate the egg and vanilla extract into the creamed mixture, mixing until fully blended for a smooth batter.
- Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt to evenly distribute the leavening agents and seasoning.
- Combine Wet and Dry: Gradually add the dry ingredients into the wet mixture, stirring gently until just combined to avoid overmixing, which can toughen the cookies.
- Prepare Topping Sauce: In a small saucepan over medium heat, melt ¼ cup of unsalted butter with the brown sugar, stirring continuously until the mixture becomes bubbly and smooth to create a caramelized topping.
- Add Topping to Bakeware: Spoon about one tablespoon of the butter-sugar mixture into the center of each cookie spot on the prepared baking sheets to form the base layer of the topping.
- Arrange Pineapple and Cherry: Place one pineapple slice on top of each butter-sugar spot, then position a maraschino cherry in the center of the pineapple slice for a classic look and additional sweetness.
- Top with Dough: Scoop about 1 tablespoon of cookie dough and gently spread it over each pineapple slice, slightly covering the fruit but leaving some visible for a pretty presentation.
- Bake Cookies: Bake the cookies in the preheated oven for 12-15 minutes or until the edges turn a light golden brown, indicating they are cooked through.
- Cool: Allow the cookies to cool on the baking sheet for 5 minutes to firm up before transferring them to a wire rack to cool completely, preventing breakage and ensuring the topping sets properly.
Notes
- Make sure the butter is softened to room temperature for easy creaming with the sugar.
- Do not overmix the dough to keep the cookies tender.
- If you want a stronger pineapple flavor, lightly brush some reserved pineapple juice on the dough before baking.
- Use parchment paper or silicone mats to prevent sticking and for easy cleanup.
- These cookies are best enjoyed fresh but can be stored in an airtight container for up to 3 days.
- Prep Time: 10 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
