If you love the nostalgia of classic pineapple upside-down cake and the chewy comfort of homemade sugar cookies, get ready for your new favorite treat: Pineapple Upside-Down Sugar Cookies! These adorable cookies combine buttery sugar cookie dough with caramelized pineapple, sweet cherries, and a hint of tropical sunshine in every bite. They’re baked up muffin-tin style for the perfect personal-sized dessert, marrying vintage flair with modern cookie goodness. Trust me, your kitchen is about to smell incredible when you pull these out of the oven!
Ingredients You’ll Need
It doesn’t take a long ingredient list to deliver big flavor, and that’s the beauty here! Each ingredient brings something special to these Pineapple Upside-Down Sugar Cookies—from the tropical tang of pineapple to the rich warmth of brown sugar. Let’s look at what you’ll need and why it matters.
- Unsalted butter: Makes the cookie base soft, rich, and perfectly tender.
- Granulated sugar: Lends that classic chewy sweetness and helps the cookies brown nicely.
- Egg: Binds the dough and gives the cookies structure.
- Vanilla extract: Adds delicious aroma and rounds out the flavors.
- All-purpose flour: The foundation of the cookie, keeping everything together.
- Baking powder: Gives the cookies just the right lift for a soft, thick texture.
- Salt: Enhances every other flavor and keeps the sweetness in balance.
- Brown sugar: Forms that classic, caramelized base under the pineapple ring for irresistible flavor.
- Maraschino cherries: A burst of color and a sweet, juicy pop in the center of every cookie.
- Pineapple rings (canned, well-drained): The star topping! Pat them dry to keep the cookies from getting soggy.
- Pineapple juice (optional): For extra tropical flavor stirred right into the dough.
How to Make Pineapple Upside-Down Sugar Cookies
Step 1: Prepare Your Muffin Tin
Set the stage for these mini showstoppers! First, preheat your oven to 350°F (175°C) and generously grease a standard muffin tin. This helps ensure your Pineapple Upside-Down Sugar Cookies pop out easily after baking, keeping their beautiful toppings intact.
Step 2: Build the Fruity Base
Sprinkle about 2 teaspoons of brown sugar into each of 6 muffin cups. Lay a well-drained pineapple ring on top of the brown sugar in each cup, trimming the rings to fit as needed. Place half a maraschino cherry right in the center of each pineapple ring; it’s not only a burst of color, but also pure joy in every bite!
Step 3: Make the Cookie Dough
In a mixing bowl, cream together the softened butter and granulated sugar until the mixture is light and fluffy—this step builds that classic sugar cookie flavor. Beat in the egg and vanilla extract until smooth. Add the flour, baking powder, salt, and the optional pineapple juice (for a little extra zing), and mix gently just until everything comes together. The dough should be soft but not sticky.
Step 4: Assemble and Bake
Scoop about 2 tablespoons of dough and gently press it over each pineapple ring, making sure to cover the fruit entirely. This cocoon of buttery cookie dough will bake up golden and rich. Pop the pan in the oven and bake for 15 to 18 minutes, or until the cookie tops look set and lightly golden. Your kitchen will start to smell dreamy!
Step 5: Cool and Invert
After baking, let the cookies cool in the muffin tin for about 5 minutes—this helps the caramelized base set up so the fruit stays put. Then, carefully invert the cookies onto a wire rack or tray so the gorgeous pineapple and cherry topping ends up on top, just like the classic cake!
How to Serve Pineapple Upside-Down Sugar Cookies
Garnishes
A sprinkle of toasted coconut, a dusting of powdered sugar, or a small mint leaf on top can make these Pineapple Upside-Down Sugar Cookies all the more inviting. Don’t be afraid to get a little fancy—these cookies wear a garnish well!
Side Dishes
Serve alongside a scoop of vanilla ice cream or a dollop of freshly whipped cream to turn these cookies into an all-out tropical dessert plate. Even a cup of pineapple sorbet or some fresh berries makes for a lovely pairing.
Creative Ways to Present
Try nestling each cookie inside a cupcake liner for easy serving at parties, or plate them on a vintage tray for a retro-inspired touch. You can even stack them in a glass cookie jar for a dazzling centerpiece at your next gathering.
Make Ahead and Storage
Storing Leftovers
Store any leftover Pineapple Upside-Down Sugar Cookies in an airtight container, separating layers with parchment or wax paper to keep the caramelized tops from sticking. They’ll stay soft and flavorful for up to three days at room temperature.
Freezing
These cookies freeze beautifully! Once entirely cool, wrap them individually in plastic wrap and place in a freezer bag. They’ll keep for up to two months—just thaw at room temperature when ready to enjoy.
Reheating
For an irresistibly fresh taste, warm a Pineapple Upside-Down Sugar Cookie for 10–15 seconds in the microwave. The fruit topping softens, the cookie turns tender, and the aroma fills the room all over again.
FAQs
Can I make these cookies ahead of time?
Absolutely! You can prepare Pineapple Upside-Down Sugar Cookies a day in advance. Just store them in an airtight container and they’ll stay soft and delicious. For best results, serve within 24 hours of baking to keep that perfect texture.
What if I don’t have a muffin tin?
No worries! You can arrange the pineapple and cherries on a lined baking sheet, then shape the dough over the fruit. The shape may be a little more rustic, but the flavors will still shine through.
Can I use fresh pineapple instead of canned?
Yes—just slice the pineapple thinly and be sure to pat it dry very well to avoid excess juice in your cookies. Fresh pineapple gives an even brighter flavor, so feel free to go for it!
How do I keep the cookies from sticking to the pan?
Thoroughly greasing the muffin tin is key, and a nonstick spray or butter both work well. Letting the cookies cool for a few minutes before inverting also helps the caramelized bottom release beautifully.
Can I make these cookies gluten-free?
Absolutely! Substitute a 1:1 gluten-free all-purpose flour blend. The results will still be plenty chewy and delicious, so everyone can enjoy Pineapple Upside-Down Sugar Cookies.
Final Thoughts
If you’re craving something playful, colorful, and guaranteed to impress, Pineapple Upside-Down Sugar Cookies are calling your name. With their sunny flavors and charming presentation, they’re a true treat to bake and share. Give them a try—you just might discover your newest dessert obsession!
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
Indulge in a tropical treat with these Pineapple Upside-Down Sugar Cookies. A delightful twist on the classic dessert, these mini delights feature a buttery sugar cookie base topped with caramelized pineapple rings and cherries.
Ingredients
Cookies:
- 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
Toppings:
- 1/4 cup brown sugar
- 6 maraschino cherries, halved
- 6 pineapple rings (canned, well-drained and patted dry)
- Optional: 1 tablespoon pineapple juice
Instructions
- Preheat the oven: Preheat the oven to 350°F (175°C) and grease a muffin tin well.
- Prepare the base: Sprinkle about 2 teaspoons of brown sugar into the bottom of each of 6 muffin cups. Place a pineapple ring in each cup, trimming if needed, and add half a cherry to the center of each ring.
- Make the cookie dough: Cream butter and granulated sugar, then beat in egg and vanilla. Mix in flour, baking powder, salt, and pineapple juice (if using).
- Assemble the cookies: Press cookie dough over each pineapple ring and bake for 15–18 minutes until golden.
- Finalize and serve: Let cool in the tin for 5 minutes, then invert onto a wire rack. Serve warm or at room temperature.
Notes
- Ensure pineapple slices are well-drained to prevent soggy cookies.
- Try crushed pineapple for smaller bites or add coconut extract for a tropical flavor.
Nutrition
- Serving Size: 1 cookie
- Calories: 240
- Sugar: 21g
- Sodium: 90mg
- Fat: 11g
- Saturated Fat: 7g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 33g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 40mg
