Pineapple Upside Down Sugar Cookies Recipe
If you’ve ever wished you could combine the buttery, caramelized magic of a classic pineapple upside down cake with the nostalgia of a soft sugar cookie, these Pineapple Upside Down Sugar Cookies will absolutely steal your heart. Each bite delivers a burst of sweet pineapple, a hint of cherry, and the soft, chewy deliciousness of your favorite homemade cookie, all wrapped up together in a single handheld treat. Perfect for celebrations, sharing with friends, or just making an average Tuesday unforgettable, this recipe is sunshine in dessert form!
Ingredients You’ll Need
There’s something so comforting about a recipe that starts with simple, everyday ingredients yet ends up tasting like something truly special. Each item here isn’t just for show—they all play their role in delivering tender cookies with caramelized tops and bright pops of flavor.
- Butter (1 cup, room temperature): Softened butter is key for a beautifully creamy and fluffy cookie base.
- Granulated Sugar (1 1/2 cups): Provides sweetness and that signature sugar cookie texture.
- Eggs (2): Help bind the dough and add rich flavor.
- Vanilla Extract (2 tsp.): Just a little boosts all the other flavors and gives depth.
- Sour Cream (1/2 cup): Makes for extra softness and a delicate tang in every bite.
- All-Purpose Flour (3 cups): The sturdy foundation for these cookies to hold all their toppings.
- Baking Powder (1 tsp.): Gives these cookies a perfect lift.
- Cornstarch (1 tsp.): Adds tenderness for that classic sugar cookie crumb.
- Salt (1/2 tsp.): Balances out the sweetness.
- Canned Pineapple Slices (13): Each slice crowns a cookie with juicy, tropical goodness.
- Maraschino Cherries (13): The classic touch of color and just the right amount of cherry pop.
- Butter (1/2 cup, melted): Used to create the gooey brown sugar topping.
- Light Brown Sugar (1 cup, packed): Caramelizes into that iconic sticky-sweet layer atop every cookie.
How to Make Pineapple Upside Down Sugar Cookies
Step 1: Preheat Your Oven and Prep the Pan
Start by preheating your oven to 350 degrees Fahrenheit. Get your mini round cake pan ready—this specialty pan is perfect for capturing all the gooey caramel topping. Set it aside while you mix the dough so you can work quickly when it comes time to layer the ingredients.
Step 2: Cream Together the Butter and Sugar
In a large mixing bowl, beat the softened butter and granulated sugar together until the mixture looks pale and feels fluffy. This step is crucial—it traps air in the dough, leading to lighter, tender cookies with just the right amount of chew.
Step 3: Add Eggs, Vanilla, and Sour Cream
Mix in the eggs one at a time, along with vanilla extract and sour cream. The eggs bind everything together and the vanilla makes the kitchen smell amazing, while the sour cream gives your sugar cookie base an irresistible softness.
Step 4: Incorporate the Dry Ingredients
Gently add in the flour, baking powder, cornstarch, and salt. Stir just until the dough forms; no need to overmix. Your dough should look thick and cohesive, perfect for topping the fruit and brown sugar in the next steps.
Step 5: Make the Brown Sugar Mixture
In a separate bowl, stir together the melted butter and light brown sugar until it looks uniform and glossy. This mixture is responsible for that dreamy caramel layer once the cookies are baked and flipped.
Step 6: Assemble the Pan with Toppings
Add about a tablespoon of the brown sugar mixture into the bottom of each cavity in your pan, spreading it out evenly. Place one pineapple slice on top of this sweet base, and then tuck a maraschino cherry right in the center of each ring—it’s a little retro, a little fancy, and a whole lot of delicious.
Step 7: Scoop and Flatten the Cookie Dough
Using a 3-tablespoon cookie scoop, drop a mound of dough on top of each fruit-filled cavity. Use an offset spatula (or the back of a spoon) to gently flatten the dough so it covers the pineapple and reaches the edges. This helps the cookies bake up evenly and soak in all those luscious flavors underneath.
Step 8: Bake to Golden Perfection
Slide your pan into the preheated oven and bake for about 25 minutes. Watch for the edges to turn golden brown and for the brown sugar to bubble enthusiastically up the sides of each mini well—that’s a sign you’re getting the perfect caramelization.
Step 9: The Flip and the Cool-Down
Let the cookies cool in the pan for 10 minutes. Place a piece of wax paper on your counter, then carefully invert the cookies onto it. The brown sugar sauce will drip everywhere, so the wax paper is essential for easy cleanup. If any pineapple stays behind in the pan, simply place it back on top of the cookie—no one will ever know!
Step 10: Let Them Set Before Serving
Let your Pineapple Upside Down Sugar Cookies cool completely before serving. The flavors meld, the toppings set, and you’re left with irresistible cookies that hold together beautifully but are still soft and moist. Store leftovers in an airtight container for maximum freshness.
How to Serve Pineapple Upside Down Sugar Cookies
Garnishes
For a little extra flair, dust your cookies with a bit of powdered sugar right before serving. A dollop of whipped cream, a drizzle of caramel, or even a small scoop of vanilla ice cream nestled on the plate transforms these cookies into a plated dessert worthy of your favorite bistro. And don’t forget a twist of fresh lime zest for a pop of color and zing.
Side Dishes
You truly can’t go wrong pairing these cookies with a big fruit salad, especially on a hot day. A cold glass of iced hibiscus tea, or even coffee with a splash of coconut milk, complements the tropical flavors beautifully and helps round out the treat as part of a special brunch or casual gathering.
Creative Ways to Present
Arrange Pineapple Upside Down Sugar Cookies on a tiered cake stand for an eye-catching dessert table centerpiece, or wrap them individually in clear cellophane bags for adorable party favors. For a playful twist, try stacking two cookies together with a swirl of piped buttercream in the middle to make a “cookie sandwich” destined to impress a crowd!
Make Ahead and Storage
Storing Leftovers
Keep your cookies moist and flavorful by storing leftovers in an airtight container at room temperature. The caramel topping and juicy fruit mean they’re best enjoyed within 2 to 3 days—if they last that long! Make sure the cookies are completely cool before sealing them up so condensation doesn’t make them soggy.
Freezing
You can absolutely freeze Pineapple Upside Down Sugar Cookies for longer storage. Layer them between sheets of parchment paper inside a freezer-safe container to keep the fruit and topping from sticking. They’ll keep their best quality for about 2 months—just remember to thaw them in the fridge before serving for best texture.
Reheating
If you crave that just-baked warmth, pop a cookie in the microwave for about 10 seconds or give it a quick trip through a low oven (at 300 degrees) until it’s gently warmed through. This revives the caramel topping and brings those tropical aromas right back to life.
FAQs
Can I use fresh pineapple instead of canned?
Yes, you can! Just be sure to cut the pineapple slices to a thickness similar to canned ones and pat them dry to avoid excess juice making the cookies soggy. Fresh pineapple can make the treats even more vibrant and flavorful.
What should I do if my pineapple or cherry sticks to the pan?
No worries at all. Simply lift out the stuck fruit and reposition it on top of your warm cookie while it’s still soft. The brown sugar glaze is forgiving and will help everything stick together as it cools.
Can I prepare the dough ahead of time?
Absolutely! You can make the cookie dough a day ahead, wrap it tightly, and refrigerate. Let the dough sit at room temperature for about 20 minutes before assembling the cookies as it’ll be easier to scoop and spread.
Do I need a special mini cake pan for this recipe?
The mini round cake pan works best for the classic look, but you can use large muffin tins in a pinch. Just be sure to grease them well and watch the baking time as some ovens run hotter than others.
Can I make Pineapple Upside Down Sugar Cookies gluten-free?
Yes, simply substitute your favorite one-to-one gluten free flour blend for the all-purpose flour. Keep an eye on the consistency of your dough, as some blends absorb more moisture than others, but you should still get delicious, beautiful results!
Final Thoughts
If you’re looking for an unforgettable twist on two classic desserts, Pineapple Upside Down Sugar Cookies are a must-bake. With their bright flavors, gooey caramel tops, and chewy sugar cookie base, they bring all the joy of a homemade treat with a fun, modern flair. Don’t be surprised if these sunny cookies become your new go-to recipe—give them a try and share a little slice of sunshine with everyone you love!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Total Time: 45 minutes
- Yield: Makes 13 cookies 1x
- Diet: Vegetarian
Description
These Pineapple Upside Down Sugar Cookies are a delightful twist on the classic cake version. Soft and chewy cookies with a caramelized pineapple slice and a maraschino cherry on top, perfect for any occasion.
Ingredients
Cookies:
- 1 cup butter (room temperature)
- 1 1/2 cups granulated sugar
- 2 eggs
- 2 tsp. vanilla extract
- 1/2 cup sour cream
- 3 cups all-purpose flour
- 1 tsp. baking powder
- 1 tsp. cornstarch
- 1/2 tsp. salt
Topping:
- 13 canned pineapple slices
- 13 maraschino cherries
- 1/2 cup butter (melted)
- 1 cup light brown sugar (packed)
Instructions
- Preheat oven to 350 degrees. Prepare mini round cake pan.
- Cream together butter and sugar until light and fluffy.
- Add eggs, vanilla, and sour cream; mix well.
- Incorporate flour, baking powder, cornstarch, and salt until just combined. Set aside.
- Combine melted butter and brown sugar in a separate bowl.
- Place a spoon of brown sugar mixture in each cavity, then top with pineapple slice and cherry.
- Add cookie dough on top, flatten with spatula.
- Bake for 25 minutes until golden and bubbly.
- Cool for 10 minutes, then turn out onto wax paper.
- Let cool completely before storing in airtight container.
Notes
- Ensure pineapple and cherries are well-drained to prevent excess moisture.
- Adjust baking time based on oven variations for perfect doneness.
- Prep Time: 20 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 240
- Sugar: 18g
- Sodium: 170mg
- Fat: 12g
- Saturated Fat: 7g
- Unsaturated Fat: 4g
- Trans Fat: 0g
- Carbohydrates: 32g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 50mg
Keywords: Pineapple Upside Down Sugar Cookies, Pineapple Cookies, Upside Down Cookies, Dessert Recipe
