Pineapple Upside Down Sugar Cookies Recipe
If you love the magic of classic pineapple upside down cake but crave the buttery crunch of a perfect sugar cookie, the Pineapple Upside Down Sugar Cookies Recipe is about to become your new baking obsession. Imagine golden discs of sweet-tart pineapple and bright maraschino cherries, all hugged by a rich layer of caramelized brown sugar, tucked under a chewy sugar cookie cap. These cookies are a breeze to make, bringing vintage charm and fun, colorful vibes to any table—and the irresistible flavor is pure nostalgia in every bite.
Ingredients You’ll Need
The beauty of the Pineapple Upside Down Sugar Cookies Recipe is in its simplicity: a handful of pantry staples and a few classic toppings come together to create an unforgettable treat. Each ingredient plays a starring role in taste, texture, and visual appeal.
- Refrigerated sugar cookie dough (1 roll, 16.5 oz): The ultimate shortcut, delivering tender, buttery cookies every time with practically zero effort.
- Brown sugar (1/4 cup): Creates that irresistible caramelized topping that pairs perfectly with pineapple.
- Unsalted butter (2 tablespoons, melted): Blends with brown sugar for extra richness and helps everything caramelize beautifully.
- Maraschino cherries (12): These add a pop of color and a bright sweetness right in the center of every cookie.
- Crushed pineapple (1/2 cup, well-drained): Tropical flavor and a touch of tang—the drained pineapple prevents sogginess and keeps things perfectly chewy.
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). Lightly grease a 12-cup muffin tin or pop in silicone muffin liners for easy release later. This step is key to getting those beautiful, intact cookies out of the pan.
Step 2: Mix Brown Sugar and Butter
In a small bowl, stir together the melted unsalted butter and brown sugar. This forms the sweet, gooey layer that caramelizes on the bottom of each cookie, just like the classic cake we all love.
Step 3: Build the Pineapple Upside Down Layer
Spoon about one teaspoon of the brown sugar mixture into the bottom of each prepared muffin cup. Press a maraschino cherry into the center, then add about one tablespoon of crushed pineapple around each cherry. The key is to make sure the pineapple is well-drained so you don’t end up with soggy cookies!
Step 4: Top with Sugar Cookie Dough
Slice your sugar cookie dough into twelve even pieces. Flatten each slice with your hands, then place over the pineapple and cherry in each muffin cup. Gently press down to cover the fruit—you want every bite to have that sweet cookie finish.
Step 5: Bake to Golden Perfection
Bake for 12 to 15 minutes, or until the cookies are lightly golden around the edges. The aroma at this point will be absolutely irresistible! Allow the cookies to cool in the pan for 5 to 10 minutes so the caramelized layer can set before you remove them.
Step 6: Invert and Cool
Carefully run a knife around each cookie to loosen the edges, then invert onto a wire rack or platter while still slightly warm. Admire your colorful, glossy Pineapple Upside Down Sugar Cookies Recipe creations!
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
For a festive finish, add an extra maraschino cherry on top just before serving, or sprinkle with a dusting of powdered sugar. If you love a little spice, a whisper of cinnamon or nutmeg over the top can make these cookies truly pop.
Side Dishes
Serve these cookies with scoops of vanilla or coconut ice cream for a retro-inspired dessert plate. Fresh berries or a fruit salad also complement the tropical flavors nicely, adding a burst of freshness to each bite.
Creative Ways to Present
Arrange your cookies on a vintage cake stand for a show-stopping centerpiece, or tuck them in colorful paper muffin cups for grab-and-go treats at picnics and parties. For extra fun, stack two cookies with a slather of whipped cream between them—think of it as a Pineapple Upside Down Sugar Cookies Recipe sandwich!
Make Ahead and Storage
Storing Leftovers
Store any leftover cookies in an airtight container at room temperature for up to three days. Because of the fruit layer, it’s best to separate layers with wax or parchment paper to keep them from sticking together.
Freezing
To freeze, let the cookies cool completely and then wrap them individually in plastic wrap or foil. Place the wrapped cookies in a freezer-safe bag or container and freeze for up to one month. Thaw at room temperature for a few hours before enjoying.
Reheating
If you want to recapture that fresh-baked taste, gently reheat cookies in a 300°F oven for 5–7 minutes. This brings the caramel layer back to life and makes the cookies taste like they just came out of the oven.
FAQs
Can I use fresh pineapple instead of canned?
Yes, you absolutely can! Just chop your fresh pineapple into tiny pieces and pat them dry thoroughly before using. The key is to avoid excess moisture so your cookies bake up perfectly chewy, not soggy.
Do I need to use muffin liners?
Muffin liners are optional but can make cleanup a breeze and ensure easy removal. If you prefer, a good coat of nonstick spray or butter will also do the trick—just be sure to run a knife gently around the edge before inverting.
Can I make this recipe gluten-free?
Absolutely! Swap in your favorite refrigerated gluten-free sugar cookie dough. Always double-check that your brown sugar and other toppings are gluten-free just to be safe.
How can I add extra flavor?
Try mixing a pinch of cinnamon or a dash of nutmeg into the brown sugar mixture for a warm, spicy note. Or add a small splash of pineapple juice to the sugar and butter mixture for a deeper pineapple flavor.
Can I double the Pineapple Upside Down Sugar Cookies Recipe for a party?
Definitely! Simply prepare two muffin tins, and you’re all set to make two dozen cookies in one go. You might want to rotate the trays halfway through the baking time to ensure even browning.
Final Thoughts
If you’re looking for a playful twist on a beloved classic, the Pineapple Upside Down Sugar Cookies Recipe is impossible to resist. These cookies are as easy to bake as they are to devour, so roll up your sleeves and share a batch with your favorite people—your taste buds will thank you!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Total Time: 25 minutes
- Yield: 12 cookies 1x
- Diet: Vegetarian
Description
Indulge in these delightful Pineapple Upside Down Sugar Cookies that combine the classic flavors of a pineapple upside-down cake with the convenience of a cookie. These sweet treats are perfect for any occasion and will surely impress your guests!
Ingredients
Ingredients:
- 1 roll (16.5 oz) refrigerated sugar cookie dough
- 1/4 cup brown sugar
- 2 tablespoons unsalted butter, melted
- 12 maraschino cherries
- 1/2 cup crushed pineapple, well-drained
Instructions
- Preheat the oven: Preheat the oven to 350°F (175°C). Lightly grease a 12-cup muffin tin or line with silicone liners.
- Prepare the base: Mix melted butter and brown sugar. Spoon mixture into each muffin cup. Add a cherry in the center and pineapple around it.
- Layer the cookies: Slice cookie dough, flatten pieces, and place over the pineapple in each cup.
- Bake: Bake for 12–15 minutes until golden brown. Cool, then invert onto a rack.
Notes
- Make sure the pineapple is well-drained to prevent sogginess.
- For extra flavor, add a pinch of cinnamon to the brown sugar mixture or use a splash of pineapple juice in the glaze.
- Prep Time: 10 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 190
- Sugar: 19g
- Sodium: 125mg
- Fat: 8g
- Saturated Fat: 3g
- Unsaturated Fat: 5g
- Trans Fat: 0g
- Carbohydrates: 28g
- Fiber: 0g
- Protein: 1g
- Cholesterol: 10mg
