If you adore the nostalgic charm of pineapple upside-down cake but crave something a bit more bite-sized and fun to share, then you’re going to fall head over heels for this Pineapple Upside-Down Sugar Cookies Recipe. These delightful treats capture all the tropical sweetness of caramelized pineapple and maraschino cherries atop buttery sugar cookies, creating a playful twist that’s perfect for any occasion. With their chewy texture, golden edges, and vibrant fruity toppings, these cookies are a guaranteed crowd-pleaser that bring sunshine straight to your kitchen.
Ingredients You’ll Need
Getting started with the Pineapple Upside-Down Sugar Cookies Recipe is refreshingly simple, and each ingredient plays a starring role in delivering that signature taste and texture. From the sweet and buttery cookie dough to the luscious pineapple and cherries, every component adds a layer of flavor and brightness.
- Refrigerated sugar cookie dough (1 roll / 16.5 ounces): Provides a soft, buttery base that bakes up with tender edges and a sweet crumb.
- Brown sugar (1/3 cup): Adds deep caramel notes and creates a sticky, glossy bottom once baked.
- Unsalted butter, melted (2 tablespoons): Combines with brown sugar to form the luscious caramel-like bed beneath each cookie.
- Maraschino cherries, halved (12 total): Bright bursts of sweet color that crown each cookie and complement the tropical flavor.
- Crushed pineapple, well drained (1/2 cup): The tropical star ingredient, offering juicy sweetness without any excess moisture to keep cookies crisp.
How to Make Pineapple Upside-Down Sugar Cookies Recipe
Step 1: Prepare Your Pan and Caramel Mixture
Start by preheating your oven to 350°F and lightly greasing a 12-cup muffin tin to ensure easy cookie removal later. In a small bowl, whisk together the melted butter and brown sugar until smooth and combined. This mixture will form the beautifully caramelized bed that brings the “upside-down” magic to these sugar cookies.
Step 2: Layer the Toppings
Spoon about one teaspoon of the butter and brown sugar mixture into the bottom of each muffin cup. Then, place half a maraschino cherry right in the center for that iconic pop of color. Surround the cherry with about two teaspoons of crushed, well-drained pineapple, making sure it’s evenly spread around but not overflowing. This layered combo is what infuses each cookie with tropical charm.
Step 3: Add the Cookie Dough
Unroll the refrigerated sugar cookie dough and divide it into 12 equal pieces. Flatten each portion gently with your hands or a rolling pin into a round disk that will snugly fit over the pineapple mixture in each muffin cup. Place one flattened piece of dough on top of each fruit layer, making sure it completely covers the pineapple and cherry.
Step 4: Bake to Golden Perfection
Slide the muffin tin into the preheated oven and bake your goodies for 12 to 15 minutes. You’re looking for golden edges and a cookie that has set but remains tender inside. Keep an eye on that beautiful caramel bubbling underneath—it’s a sure sign everything is coming together perfectly.
Step 5: Cool and Invert
Once baked, allow the cookies to cool in the pan for about 5 minutes. Then carefully run a knife around the edges of each muffin cup to loosen the cookies. Now, the fun part—gently invert each cookie onto a cooling rack or tray to reveal the glossy, fruity pineapple upside-down topping. Serve warm or at room temperature for maximum joy.
How to Serve Pineapple Upside-Down Sugar Cookies Recipe
Garnishes
These cookies shine beautifully on their own, but adding a dollop of whipped cream or a sprinkle of toasted coconut flakes can instantly elevate the presentation and enhance the tropical vibe. A light dusting of powdered sugar also adds a delicate sweetness and pretty finish perfect for afternoon treats.
Side Dishes
Pair these Pineapple Upside-Down Sugar Cookies Recipe treats with a scoop of vanilla ice cream or alongside a refreshing cup of iced tea or coffee. Their sweet, fruity crunch also works wonderfully as part of a dessert platter featuring fresh fruit, cheese, and nuts for a balanced indulgence.
Creative Ways to Present
Try serving these cookies on a wooden board garnished with pineapple leaves or tropical flowers for a festive centerpiece. For parties or gifts, stack them in a pretty box with wax paper in between layers. You can even turn them into mini parfaits by layering crumbled cookies with pineapple chunks and cream in small glasses.
Make Ahead and Storage
Storing Leftovers
Once cooled completely, store any leftover cookies in an airtight container at room temperature. They stay fresh and chewy for up to 3 days, making them an easy grab-and-go snack or dessert throughout the week.
Freezing
If you want to enjoy these cookies later, they freeze beautifully. Place them in a single layer on a baking sheet until frozen solid, then transfer to a resealable freezer bag or airtight container. Frozen cookies maintain their texture and flavor for up to 2 months.
Reheating
For that just-baked warmth and soft texture, reheat frozen or refrigerated cookies in a 300°F oven for about 5 minutes or until warmed through. This little trick refreshes the caramel layer and makes each bite feel freshly baked.
FAQs
Can I make this Pineapple Upside-Down Sugar Cookies Recipe with homemade cookie dough?
Absolutely! Homemade sugar cookie dough can add a lovely personal touch. Just be sure your dough is chilled and not too sticky so it layers neatly over the fruit in each muffin cup.
What’s the best way to drain the crushed pineapple?
Place the crushed pineapple in a fine mesh strainer or coffee filter and press gently with the back of a spoon or paper towels to remove extra moisture. This prevents soggy cookie bottoms and melts the perfect caramel layer.
Can I substitute maraschino cherries with fresh cherries?
Maraschino cherries provide a sweet, juicy, and colorful contrast that fresh cherries might not replicate exactly. Fresh cherries can be used but may affect texture and sweetness, so consider lightly sweetening them before adding.
Are these cookies suitable for vegetarians?
Yes, this Pineapple Upside-Down Sugar Cookies Recipe is vegetarian-friendly as it contains no meat products and uses ingredients like butter and egg-free dough options can also be used if desired.
How do I prevent the pineapple from making the cookies soggy?
Draining the pineapple thoroughly is key. Using crushed pineapple instead of chunks helps distribute moisture evenly, and baking them promptly ensures the cookies maintain their crisp edges with a moist, flavorful topping.
Final Thoughts
There’s something incredibly special about the Pineapple Upside-Down Sugar Cookies Recipe that brings out the joyful spirit of sharing sweet moments with friends and family. Whether you’re baking for a tropical-themed party or simply craving a unique cookie experience, these bite-sized delights never disappoint. Dive into the delicious contrast of caramel, pineapple, and cherry goodness today—you’ll wonder how you ever lived without them!
