Get ready to fall in love with Pineapple Upside-Down Cookies—a dessert that packs all the gooey, sunshiny nostalgia of the classic cake into bite-sized wonders! Imagine a burst of tropical pineapple, a pop of cherry, and that rich brown sugar caramel, all wrapped in a soft, buttery cookie. These little gems are a showstopper on any dessert table, and you won’t believe how easy they are to make! Perfect for parties, potlucks, or anytime you need a slice of summer on your plate, Pineapple Upside-Down Cookies are every bit as satisfying as their old-fashioned inspiration.
Ingredients You’ll Need
Every ingredient here plays its part in creating those signature flavors and gorgeous layers, from the tangy pineapple and sweet cherries to the warm caramelized top. Grab these simple staples for the crispiest edges, fluffiest crumb, and that irresistible tropical bite.
- Unsalted butter (softened): Essential for a rich, tender crumb—using unsalted lets you control the salt perfectly.
- Light brown sugar (packed): This gives both the cookies and their topping that classic caramel taste and sticky texture.
- Granulated sugar: Offers sweetness that balances out the brown sugar and keeps the cookies light.
- Large eggs: Bind the dough and make the cookies extra soft and cakey.
- Vanilla extract: Adds warmth and depth that enhances all the fruity flavors.
- All-purpose flour: The backbone of the cookie, giving the right amount of structure.
- Baking powder: Helps the cookies rise for a light, fluffy texture.
- Baking soda: Adds lift and just a touch of golden color.
- Salt: A pinch rounds out the sweetness and intensifies all the flavors.
- Crushed pineapple (drained): Brings juicy, tropical bursts—draining well prevents soggy cookies.
- Maraschino cherries (halved): Iconic, sweet pops of color and flavor right in the center.
- Pineapple juice: Infuses both the cookie and topping with pineapple flavor.
- Light brown sugar (for topping): Melts and caramelizes for that signature gooey finish.
- Unsalted butter (melted): Ensures the topping is luscious, not dry.
How to Make Pineapple Upside-Down Cookies
Step 1: Prep Your Muffin Tin
Start by preheating your oven to 350°F (175°C). Lightly grease or line a standard muffin tin with paper liners—a generous spray will help the cookies release perfectly after baking. This step ensures that the sticky caramel topping comes out clean and beautiful every time.
Step 2: Make the Pineapple Topping
In a small bowl, combine ½ cup of light brown sugar with the melted butter, mixing until it becomes a thick, glossy caramel. Spoon about 1 teaspoon of this golden mixture into the bottom of each muffin cup. This little pool will transform into the signature sticky topping as the cookies bake!
Step 3: Add Cherries and Pineapple
Gently press half a maraschino cherry in the center of each muffin cup, right into the brown sugar mixture. Spoon a small mound of well-drained crushed pineapple over the cherry. The fruit layer will bubble and caramelize, bursting with vibrant color and flavor.
Step 4: Cream Butter and Sugars
In a large bowl, beat together the softened butter, packed brown sugar, and granulated sugar until the mix turns light, fluffy, and almost mousse-like. This airiness is crucial for giving the Pineapple Upside-Down Cookies their fine, moist crumb.
Step 5: Add Eggs and Vanilla
Crack in the eggs, one at a time, making sure each is fully incorporated before adding the next. Pour in the vanilla extract, and beat again—the batter should smell absolutely irresistible already!
Step 6: Combine Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. This quick step ensures your leaveners are evenly mixed, setting you up for cookies with perfect lift and texture.
Step 7: Mix Dry and Wet, Add Pineapple Juice
Gradually add the dry ingredients to the wet, alternating with splashes of pineapple juice. Mix just until everything comes together—over-mixing can toughen the dough, and we want our Pineapple Upside-Down Cookies soft and tender!
Step 8: Portion and Bake
Spoon enough cookie dough over each fruit-filled muffin cup to fill about three-quarters full. Don’t worry if things look a little messy, as the cookies will puff and seal in all the fruity goodness. Bake for 18 to 22 minutes, or until the tops are golden and a toothpick inserted into the center comes out clean.
Step 9: Cool and Invert
Let your cookies cool in the tin for five minutes (no longer, or the topping can stick). Run a knife gently around the edges if needed, then swiftly invert onto a wire rack. Marvel at those gorgeous, glistening Pineapple Upside-Down Cookies as the buttery brown sugar and fruit become the star!
How to Serve Pineapple Upside-Down Cookies
Garnishes
A little flourish goes a long way! Try a whisper of powdered sugar, a dollop of whipped cream, or even a sprinkle of toasted coconut on each cookie for extra color and contrast. If you want to lean into the tropical vibes, a tiny wedge of fresh pineapple or a mint sprig tucked alongside each one is delightful.
Side Dishes
Pineapple Upside-Down Cookies pair beautifully with light, creamy desserts—think vanilla ice cream or a tangy fruit salad tossed with lime zest. For a dessert tray, include chocolate-dipped strawberries, citrus bars, or coconut macaroons to highlight the cookies’ sunny flavors.
Creative Ways to Present
Turn your cookies into charming gifts by tucking each one into a colorful cupcake wrapper and wrapping in cellophane. For parties, arrange them in a spiral on a cake stand and scatter extra maraschino cherries around for a retro look. Or, make mini versions in tiny muffin tins and serve them alongside espresso shots for a playful dessert flight.
Make Ahead and Storage
Storing Leftovers
Keep your Pineapple Upside-Down Cookies tasting fresh by storing them in an airtight container at room temperature for up to three days. Place a sheet of wax paper between layers to prevent the luscious topping from sticking the cookies together, and always let them cool completely before packing.
Freezing
For longer storage, freeze the cookies in a single layer on a parchment-lined baking sheet, then transfer to a freezer bag or airtight container. They’ll keep happily in the freezer for up to two months. When you need a sweet treat, just thaw at room temperature—still chewy, fruity, and fabulous!
Reheating
To recapture that fresh-from-the-oven magic, pop your Pineapple Upside-Down Cookies in a 300°F oven for about five minutes, or until gently warmed through. This brings the caramel topping back to silky, gooey life and wakes up all those dreamy pineapple flavors.
FAQs
Do I need to use a muffin tin?
Yes, a standard muffin tin is key for shaping Pineapple Upside-Down Cookies and creating those irresistible layers. It keeps the topping contained and gives your cookies their classic, cake-like shape.
Can I make these in advance?
Absolutely! These cookies hold up well if made a day in advance. Just store them airtight after they’ve cooled to room temperature, and the flavors will meld beautifully overnight.
What if I don’t have maraschino cherries?
No problem! You can swap in candied cherries, fresh cherries (pitted and halved), or even a small spoonful of extra pineapple for a slightly different twist. The look and flavor will still shine.
Can I make mini versions?
Definitely—just use a mini muffin tin and shorten the baking time by about 5 minutes. The result is irresistible bite-sized Pineapple Upside-Down Cookies perfect for parties or snacking.
How do I prevent the cookies from sticking?
Thoroughly greasing your muffin tin (or using parchment muffin liners) and letting the cookies cool just five minutes before inverting are both essential. Warm cookies release more easily, keeping your caramel topping intact.
Final Thoughts
I have to say, if you love a bright, tropical dessert with a nostalgic twist, give these Pineapple Upside-Down Cookies a try. They’re simple, stunning, and guaranteed to win over every cookie lover (and cake lover!) you know. Set aside a little time, share a batch with friends, and get ready for rave reviews!
Print
Pineapple Upside-Down Cookies Recipe
- Prep Time: 20 minutes
- Cook Time: 20 minutes
- Total Time: 40 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These Pineapple Upside-Down Cookies are a delightful twist on the classic cake version. With a buttery cookie base topped with caramelized pineapple and cherries, they are perfect for individual servings.
Ingredients
Cookie Dough:
- 1 cup unsalted butter, softened
- 1 cup light brown sugar (packed)
- ½ cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 2¼ cups all-purpose flour
- 1 teaspoon baking powder
- ½ teaspoon baking soda
- ½ teaspoon salt
Topping:
- ½ cup crushed pineapple (drained)
- 12 maraschino cherries (halved)
- ¼ cup pineapple juice
- ½ cup light brown sugar (for topping)
- 2 tablespoons unsalted butter (melted)
Instructions
- Preheat and Prepare: Preheat the oven to 350°F (175°C) and prepare a muffin tin with liners or light greasing.
- Prepare Topping: Mix ½ cup brown sugar and melted butter, spoon a teaspoon into each muffin cup, add cherry half, and crushed pineapple.
- Make Cookie Dough: Cream butter and sugars, add eggs and vanilla, then mix in dry ingredients alternately with pineapple juice.
- Fill and Bake: Spoon dough over topping in muffin cups, bake for 18–22 minutes until golden and cooked through.
- Cool and Serve: Let cool in the tin for 5 minutes, then invert onto a wire rack to serve warm or at room temperature.
Notes
- Enhance with cinnamon for extra flavor.
- Ensure pineapple is well-drained to prevent sogginess.
- Mini muffin tins can be used for bite-sized versions.
Nutrition
- Serving Size: 1 cookie
- Calories: 230
- Sugar: 20g
- Sodium: 115mg
- Fat: 12g
- Saturated Fat: 7g
- Unsaturated Fat: 4g
- Trans Fat: 0g
- Carbohydrates: 30g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 40mg
