If you’re craving a delightful twist on classic cookies that will transport your taste buds straight to a tropical paradise, this Pineapple Upside Down Sugar Cookies Recipe is exactly what you need. Combining the buttery richness of sugar cookie dough with the caramelized sweetness of brown sugar, juicy pineapple tidbits, and vibrant maraschino cherries, these bite-sized treats bring all the joy of a pineapple upside down cake into a perfectly portable cookie. Every bite bursts with fruity goodness and a hint of coconut that makes you smile, making this recipe an irresistible favorite for gatherings, snack time, or anytime you want to indulge in a little sunny sweetness.
Ingredients You’ll Need
This recipe shines because it keeps things simple, letting each ingredient shine while effortlessly coming together to create something truly special. From the melted butter that caramelizes the sugar, to the vibrant cherries and succulent pineapple, every component adds a layer of flavor, color, and texture that makes these cookies unforgettable.
- 1/2 cup unsalted butter, melted: This creates the luscious base that caramelizes the brown sugar perfectly in each muffin cup.
- 1/2 cup brown sugar, packed: Adds rich, deep sweetness that turns golden and gooey during baking.
- 12 maraschino cherries, halved: Their bright color and juicy pop create that signature pineapple upside down look and flavor.
- 1 can (20 ounces) pineapple tidbits, well drained: Sweet and tangy bites of tropical fruit that complement the cookie dough beautifully.
- 1 roll (16.5 ounces) refrigerated sugar cookie dough: The easy shortcut that ensures soft, buttery cookies with minimal effort.
- 1/2 cup shredded sweetened coconut (optional): Adds a delicious tropical flair and extra texture if you’re feeling adventurous.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Prepare Your Muffin Tin
Start by preheating your oven to 350°F (175°C) and lightly greasing a 12-cup muffin tin. This step is key to making sure your cookies release easily after baking and helps the caramelized sugar layer stick beautifully to the cookie tops once inverted.
Step 2: Create the Caramelized Base
Divide the melted butter evenly among the muffin cups, then sprinkle each cup with the packed brown sugar. For an even richer caramel flavor, you can bake this mixture for 2 minutes before adding the fruit and dough, but that’s totally optional if you want to keep things quick.
Step 3: Add the Fruit
Place one cherry half right in the center of each cup, then surround it with a few pineapple tidbits. This arrangement gives you that authentic pineapple upside down style and ensures each cookie has a fruity burst in every bite.
Step 4: Top with Cookie Dough
Slice your refrigerated sugar cookie dough into 12 equal pieces. Press one piece gently but firmly over the fruit mixture in each muffin cup, flattening it slightly so it covers everything nicely and bakes evenly.
Step 5: Bake to Golden Perfection
Pop the muffin tin into the oven and bake for 18 to 20 minutes, until the cookies are golden brown and fully set. This is when the magic happens—the sugar caramelizes, the pineapple softens, and that cookie dough transforms into a soft, buttery top layer.
Step 6: Cool and Invert
Let the cookies cool in the pan for about 5 minutes to set the caramel, then carefully run a knife around the edges of each cup. Invert your cookies onto a baking sheet or serving platter so the caramelized fruit is perfectly displayed on top.
Step 7: Add a Coconut Finish (Optional)
Sprinkle shredded sweetened coconut over the warm cookies for an extra tropical touch. This step is totally optional but highly recommended if you love that little coconut crunch and flavor boost.
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
For a fresh and festive look, consider garnishing your Pineapple Upside Down Sugar Cookies Recipe with a light dusting of powdered sugar or a small dollop of whipped cream. You can also drizzle a bit of caramel sauce or melt some white chocolate over the top for an extra touch of indulgence that pairs beautifully with the tropical fruits.
Side Dishes
These cookies are perfect on their own as a fruity dessert, but they also pair wonderfully with a scoop of vanilla ice cream or a cup of freshly brewed coffee. If you want to create a tropical-themed spread, serve them alongside fresh fruit salad or a light citrus sorbet to keep the flavors bright and refreshing.
Creative Ways to Present
Make your cookie platter pop by arranging each cookie on colorful paper doilies or banana leaves for a Hawaiian vibe. You can even serve them alongside mini skewers of pineapple chunks and cherries for a fun, interactive dessert setup that will wow guests at any party or casual get-together.
Make Ahead and Storage
Storing Leftovers
If you have any leftovers of this Pineapple Upside Down Sugar Cookies Recipe, store them in an airtight container at room temperature. They will keep perfectly for up to 2 days, though they’re always best enjoyed fresh for their soft texture and optimal fruit flavor.
Freezing
You can freeze these cookies by placing the cooled treats in a single layer on a baking sheet until firm, then transferring them to a freezer-safe container or bag. Wrapped well, they’ll keep for up to 2 months. Thaw overnight in the fridge before reheating gently to restore that fresh-baked taste.
Reheating
To bring your cookies back to that fresh-from-the-oven warmth, heat them in a 300°F oven for about 5 to 7 minutes. This will revive the caramel topping’s gooey texture and make the sugar cookie dough soft and tender once again. Microwave is an option too, but heating in the oven yields the best results.
FAQs
Can I use fresh pineapple instead of canned for this recipe?
Absolutely! Just be sure to drain fresh pineapple tidbits very well to avoid excess moisture that can affect the cookie texture. Fresh pineapple adds a wonderful brightness and natural sweetness that works beautifully here.
What can I substitute for maraschino cherries?
If you’re not a fan of maraschino cherries or want a more natural option, try using dried cherries or fresh red grapes sliced in half. They won’t have the same bright color but will maintain the flavorful burst in the center of each cookie.
Is it necessary to use refrigerated cookie dough?
Using refrigerated dough makes this recipe super easy and consistent, but you can absolutely make your own sugar cookie dough from scratch. Just make sure it’s firm enough to slice and press over the fruit filling without falling apart.
Can I make this recipe vegan or dairy-free?
Yes! Swap out the butter for a plant-based alternative and use a vegan sugar cookie dough recipe or brand. Make sure the brown sugar and cherries are vegan-friendly too. The coconut topping adds an extra tropical flair that pairs nicely with these substitutions.
What’s the best way to prevent sticking when inverting the cookies?
Lightly greasing the muffin tin and letting the cookies cool briefly before inverting are key steps. Running a thin knife around the edges after baking helps release the caramel layer cleanly. These tricks keep your cookies intact and beautifully presented.
Final Thoughts
If you’re looking for a fun, fruity, and utterly delicious way to enjoy the flavors of a pineapple upside down cake in a simple handheld treat, this Pineapple Upside Down Sugar Cookies Recipe should be your next bake. It’s a delightful crowd-pleaser, easy enough for beginners, and always brings a smile to the table. Give it a try—you’ll be surprised how quickly it becomes a favorite in your recipe rotation!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 20 minutes
- Total Time: 35 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These Pineapple Upside Down Sugar Cookies combine the tropical sweetness of pineapple and maraschino cherries with a soft, buttery sugar cookie base. Featuring a caramelized brown sugar and butter topping, these delightful treats are easy to prepare and perfect for serving warm as a fruity dessert.
Ingredients
Topping
- 1/2 cup unsalted butter, melted
- 1/2 cup brown sugar, packed
- 12 maraschino cherries, halved
- 1 can (20 ounces) pineapple tidbits, well drained
Cookies
- 1 roll (16.5 ounces) refrigerated sugar cookie dough
- 1/2 cup shredded sweetened coconut (optional)
Instructions
- Preheat and prepare muffin tin: Preheat your oven to 350°F (175°C) and lightly grease a 12-cup muffin tin to prevent sticking.
- Make the caramelized base: Divide the melted butter evenly among the muffin cups, then sprinkle each cup with the packed brown sugar to create a caramelized topping.
- Add fruit: Place one halved maraschino cherry in the center of each muffin cup, then arrange a few pineapple tidbits around the cherry in each cup carefully.
- Prepare cookie dough: Slice the refrigerated sugar cookie dough into 12 equal portions. Press one portion over the fruit and sugar mixture in each muffin cup, flattening them slightly to cover the filling.
- Bake the cookies: Place the muffin tin into the preheated oven and bake for 18–20 minutes or until the cookies are golden brown and set.
- Cool and invert: Allow the cookies to cool in the pan for 5 minutes. Carefully run a knife around the edges of each cup, then invert each cookie onto a baking sheet or serving platter to reveal the pineapple upside down topping.
- Add finishing touch and serve: Sprinkle the tops with shredded sweetened coconut if desired and serve the cookies warm to enjoy the best flavor and texture.
Notes
- For a more caramelized topping, you can let the butter and brown sugar mixture bake in the muffin tin for 2 minutes before adding the fruit and cookie dough.
- These cookies taste best when served fresh but can be stored in an airtight container at room temperature for up to 2 days.
