If you love classic pineapple upside-down cake but want something bite-sized and uniquely delightful, then this Pineapple Upside-Down Sugar Cookies Recipe is calling your name. These charming little cookies combine the buttery softness of sugar cookies with the caramelized sweetness of pineapple and cherries baked right on top, making every bite a tropical treat. Perfect for warm afternoons, casual gatherings, or as a special dessert, these cookies are both nostalgic and refreshingly modern—offering a fun twist that’s sure to brighten your day.
Ingredients You’ll Need
Getting these pineapple upside-down sugar cookies just right starts with simple, thoughtfully chosen ingredients. Each one plays a crucial role in crafting the perfect balance of sweet, soft, and fruity flavors that define this recipe.
- Unsalted butter, 1/2 cup, softened: Provides rich flavor and a tender crumb to the cookie dough.
- Granulated sugar, 3/4 cup: Sweetens the dough and helps create a light, fluffy texture.
- Large egg, 1: Binds ingredients together and adds moisture for soft cookies.
- Vanilla extract, 1 teaspoon: Delivers warmth and enhances the sweet flavors.
- All-purpose flour, 1 1/2 cups: Forms the structure of the cookies, yielding the perfect chew.
- Baking powder, 1/2 teaspoon: Gives a subtle lift to keep cookies tender yet light.
- Salt, 1/4 teaspoon: Balances sweetness and intensifies the overall flavor.
- Brown sugar, 1/4 cup: Added at the base of the muffin cups to caramelize under the pineapple slices.
- Maraschino cherries, 6 halved: Adds a pop of color and a sweet, slightly tangy accent.
- Pineapple rings, 6 (canned, well-drained and patted dry): The star ingredient offering juicy brightness and tropical charm.
- Optional: Pineapple juice, 1 tablespoon: Enhances pineapple flavor and adds a subtle moistness to the dough.
How to Make Pineapple Upside-Down Sugar Cookies Recipe
Step 1: Prepare Your Pan and Pineapple Base
Preheat your oven to 350°F (175°C) and grease a muffin tin thoroughly to prevent sticking. Sprinkle about 2 teaspoons of brown sugar into each of 6 muffin cups; this sugar will melt during baking, creating that classic caramelized layer. Gently press one pineapple ring into each cup on top of the sugar, trimming if necessary to fit snugly. Finish by placing half a maraschino cherry right in the center of each pineapple ring. This sets the stage for your cookies’ signature upside-down effect.
Step 2: Make the Cookie Dough
In a mixing bowl, cream the softened butter with the granulated sugar until the mixture is light and fluffy, which usually takes about 3 to 4 minutes with an electric mixer. This aeration is what gives the cookies their tender texture. Beat in the egg and vanilla extract until fully incorporated. Then, in a separate bowl, whisk together the flour, baking powder, and salt before gradually adding these dry ingredients to the wet mix. If you want an extra burst of pineapple flavor, blend in a tablespoon of pineapple juice here. Mix just until everything comes together—overmixing can make cookies tough.
Step 3: Assemble and Bake
Using a spoon or small cookie scoop, portion about 2 tablespoons of cookie dough over each pineapple ring in the muffin tin, gently pressing the dough down to cover the fruit completely. This ensures that the pineapple and cherry peek through beautifully once baked and flipped. Slide the tray into the oven and bake for 15 to 18 minutes, or until the cookie tops look set and have a light golden hue. Resist the urge to peek too often—oven heat is important for perfect rises!
Step 4: Cool and Flip
After baking, allow your cookies to rest in the muffin tin for about 5 minutes to set and cool slightly, making flipping easier. Then, carefully invert the tin onto a wire rack or tray so the cookies release with those gorgeous pineapple and cherry toppings now gloriously on the top. Let them cool completely or enjoy warm for a gooey, fresh-from-the-oven experience.
How to Serve Pineapple Upside-Down Sugar Cookies Recipe
Garnishes
You can take these cookies to the next level by adding a dollop of freshly whipped cream or a drizzle of coconut cream for extra tropical flair. A light dusting of powdered sugar or a sprinkle of toasted coconut flakes also adds a beautiful visual and textural contrast that’s sure to impress guests.
Side Dishes
Pair these cookies with a fresh fruit salad or a chilled glass of pineapple juice or sparkling lemonade to fully embrace the tropical vibe. They also make an excellent complement to afternoon tea or a light coffee break where sweetness and acidity balance each other perfectly.
Creative Ways to Present
Serve these pineapple upside-down sugar cookies on a rustic wooden platter lined with banana leaves or tropical-themed napkins for a fun presentation. For parties, stack them in a tiered dessert stand or place them in pretty cupcake wrappers and tie with raffia or colorful ribbon to give your gathering that extra special touch.
Make Ahead and Storage
Storing Leftovers
Once completely cooled, store leftover cookies in an airtight container at room temperature. They will stay fresh and flavorful for up to 3 days, making them perfect for preparing ahead of time for a weekend treat or unexpected guests.
Freezing
If you want to make these treats well in advance, freeze the baked cookies by wrapping them individually in plastic wrap and placing them in a freezer-safe bag or container. They can be frozen for up to 1 month without losing their delicious texture and flavor.
Reheating
To enjoy the cookies as if fresh, gently reheat them in a preheated oven at 300°F (150°C) for about 5 to 7 minutes. This will help revive their softness and bring out the caramel notes of the pineapple base without drying them out.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just make sure to slice fresh pineapple thinly and dry it well to avoid soggy cookies. You might want to roast the fresh slices briefly to remove excess moisture before assembling.
Is it possible to make these cookies gluten-free?
Yes! Swap the all-purpose flour for a gluten-free baking blend that measures cup-for-cup, and ensure your baking powder is gluten-free. The texture might be slightly different but equally delicious.
How do I prevent the cookies from sticking to the pan?
Grease your muffin tin thoroughly, and consider lining it with parchment paper rounds or silicone muffin liners for extra non-stick assurance, especially if your pan is older or less non-stick.
Can I substitute maraschino cherries with another fruit?
You can! Glacé cherries or even fresh raspberries work well, offering a similar burst of color and sweetness. Just be mindful of moisture content to maintain cookie texture.
What if I want a coconut flavor twist?
Add 1/2 teaspoon of coconut extract to the cookie dough or sprinkle some shredded toasted coconut on top of the pineapple before adding the dough for a wonderful tropical upgrade.
Final Thoughts
There is something truly special about the Pineapple Upside-Down Sugar Cookies Recipe that brings together nostalgic flavors with a fresh, playful format. These cookies effortlessly capture the magic of tropical sweetness in a soft, buttery bite that can brighten anyone’s day. Whether you’re sharing with friends, adding a new favorite to your baking rotation, or simply craving that perfect combo of fruit and sugar cookie, these treats are well worth making. I can’t wait for you to try them and fall in love just like I did!
Print
Pineapple Upside-Down Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 18 minutes
- Total Time: 33 minutes
- Yield: 6 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These Pineapple Upside-Down Sugar Cookies are a delightful twist on the classic dessert, combining the tropical sweetness of pineapple and maraschino cherries with a soft, buttery sugar cookie base. Perfectly portioned as mini treats, they feature a caramelized pineapple ring and cherry topping baked right into the cookie for a beautiful and delicious presentation.
Ingredients
Cookie Dough
- 1/2 cup unsalted butter, softened
- 3/4 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
- Optional: 1 tablespoon pineapple juice
Topping
- 1/4 cup brown sugar
- 6 maraschino cherries, halved
- 6 pineapple rings (canned, well-drained and patted dry)
Instructions
- Prepare the muffin tin: Preheat your oven to 350°F (175°C) and grease a muffin tin thoroughly to prevent sticking. Sprinkle about 2 teaspoons of brown sugar into the bottom of each of the 6 muffin cups.
- Add pineapple and cherries: Place one pineapple ring into each muffin cup, trimming the rings to fit if necessary. Place half a maraschino cherry in the center of each pineapple ring to create the classic upside-down topping.
- Make the dough: In a mixing bowl, cream together the softened butter and granulated sugar until the mixture is light and fluffy. Beat in the egg and vanilla extract until well combined. Then add the all-purpose flour, baking powder, salt, and pineapple juice if using, mixing just until the ingredients are combined to avoid overworking the dough.
- Assemble cookies: Scoop about 2 tablespoons of the cookie dough and gently press it over each pineapple ring, covering the topping completely.
- Bake: Place the muffin tin in the preheated oven and bake for 15 to 18 minutes or until the tops of the cookies are set and lightly golden brown.
- Cool and serve: Let the cookies cool in the muffin tin for 5 minutes. Then carefully invert each cookie onto a wire rack or tray. Serve warm or at room temperature for the best experience.
Notes
- Ensure pineapple slices are well-drained and patted dry to prevent soggy bottoms in the cookies.
- You can substitute pineapple rings with crushed pineapple for smaller bite-sized treats.
- Add a teaspoon of coconut extract to the dough for an extra tropical flavor dimension.
