If you adore the classic tropical charm of pineapple upside-down cake but prefer a portable, bite-sized treat, then this Pineapple Upside-Down Cookies Recipe is going to become your new obsession. These cookies capture all the luscious flavors of caramelized brown sugar, buttery crust, juicy crushed pineapple, and bright maraschino cherries, all packed into a soft, tender cookie. Perfectly golden with a delightful burst of pineapple on the bottom, this recipe brings a refreshing twist to your usual cookie lineup while evoking sunny, carefree summer vibes in every bite.
Ingredients You’ll Need
This Pineapple Upside-Down Cookies Recipe calls for straightforward, pantry-friendly ingredients that come together beautifully to deliver rich taste, moist texture, and that signature shiny tropical finish. Each ingredient plays a key role in achieving the perfect balance, from browning the sugar to tenderizing the cookie crumb.
- 1 cup unsalted butter, softened: Creamy fat that gives richness and helps create a tender crumb.
- 1 cup light brown sugar (packed): Adds moist sweetness and caramel notes.
- ½ cup granulated sugar: Provides balance and a hint of crispness.
- 2 large eggs: Bind the dough and help with the cookie’s structure.
- 1 teaspoon vanilla extract: Enhances and rounds out the flavors.
- 2¼ cups all-purpose flour: The base that gives cookies their body and chew.
- 1 teaspoon baking powder: Leavens gently for lightness.
- ½ teaspoon baking soda: Boosts rise and tenderness.
- ½ teaspoon salt: Balances the sweetness and intensifies flavors.
- ½ cup crushed pineapple (drained): The star ingredient providing juicy, tropical bursts.
- 12 maraschino cherries (halved): Classic colorful garnish adding a pop of sweetness.
- ¼ cup pineapple juice: Adds moisture and extra pineapple flavor to the dough.
- ½ cup light brown sugar (for topping): Creates a caramelized, sticky base layer.
- 2 tablespoons unsalted butter (melted): Helps the topping bubble and color beautifully.
How to Make Pineapple Upside-Down Cookies Recipe
Step 1: Prepare the Topping
Start by preheating your oven to 350°F (175°C) and prepare your muffin tin with either a light grease or paper liners to prevent sticking. Mix the half cup of brown sugar with the melted butter until you have a rich, sticky mixture. Spoon about one teaspoon of this into the bottom of each muffin cup to form the caramelized base that will turn the cookies upside down later. Nestle a cherry half in the center of each dollop, then add a small spoonful of well-drained crushed pineapple on top. This layering ensures that once baked and flipped, each cookie shines with that classic pineapple upside-down look and flavor.
Step 2: Cream the Butter and Sugars
In a large mixing bowl, cream together your softened butter, brown sugar, and granulated sugar until the mixture becomes light and fluffy. This step is crucial because it aerates the dough, resulting in cookies with the perfect tender yet chewy texture. The sugars dissolve and blend into the butter, promising that lovely caramelized sweetness in every bite.
Step 3: Incorporate the Eggs and Vanilla
Add the eggs one at a time, mixing thoroughly after each addition to make sure the batter stays smooth and well combined. Then, stir in the vanilla extract, which will add a fragrant depth and warmth, complementing the tropical fruit flavors beautifully.
Step 4: Combine Dry Ingredients
In a separate bowl, whisk the all-purpose flour, baking powder, baking soda, and salt together. These dry ingredients ensure your cookies get the right lift and tenderness without becoming dense or cakey. Gradually add the dry mix into the wet ingredients, alternating with the pineapple juice. This keeps the dough moist and tender without being soggy. Be careful not to overmix; stop as soon as everything is just combined to maintain the best texture.
Step 5: Assemble and Bake
Spoon your cookie dough over the pineapple and cherry mixture in each muffin cup, filling about three-quarters full to give the cookies room to rise. Bake the cookies for 18 to 22 minutes until they are beautifully golden and a toothpick inserted in the cookie portion comes out clean. Once done, let the cookies cool in the tin for 5 minutes, then carefully invert them onto a wire rack. This flipping reveals the gorgeous caramelized pineapple and cherry topping, making them visually stunning as well as delicious.
How to Serve Pineapple Upside-Down Cookies Recipe
Garnishes
A simple dollop of whipped cream on top complements these cookies perfectly, balancing their sweetness with lightness. For an extra tropical touch, sprinkle some toasted coconut flakes, or add a tiny mint leaf for a fresh pop of color and aroma that will impress at any gathering.
Side Dishes
These cookies pair wonderfully with a scoop of vanilla ice cream or a small cup of fresh fruit salad to continue the tropical theme. For an afternoon treat, serve alongside a tall glass of iced tea or coconut water to keep things refreshing and light.
Creative Ways to Present
Try serving your Pineapple Upside-Down Cookies Recipe on a wooden board with edible flowers or on a decorative platter lined with banana leaves for a festive, island-inspired presentation. Mini versions baked in smaller tins make adorable bite-sized party favors or dessert buffet treats that guests will rave about.
Make Ahead and Storage
Storing Leftovers
Store any leftover cookies in an airtight container at room temperature for up to three days to keep them soft and flavorful. Avoid refrigerating as that can dry them out, but if your kitchen is very warm, a cool spot works fine.
Freezing
These cookies freeze beautifully. Place them in a single layer on a baking sheet to freeze initially, then transfer to a freezer-safe bag or container for up to two months. Just be sure to thaw at room temperature before serving to enjoy their full flavor and soft texture.
Reheating
For a freshly baked feel, warm the cookies in a 300°F oven for 5 to 7 minutes or until gently heated through. This helps reactivate the caramelized topping’s sticky, gooey goodness, making them taste like they just came out of the oven.
FAQs
Can I use canned pineapple for the cookies?
Absolutely! Just be sure to drain the crushed pineapple very well to avoid soggy cookies. Fresh pineapple can work too, but again, remove excess juice for the best texture.
Can I make these cookies gluten-free?
Yes, by swapping the all-purpose flour with a gluten-free baking blend, you can enjoy these cookies without gluten. Just check your baking powder and other ingredients to ensure they’re gluten-free too.
Is it possible to make mini Pineapple Upside-Down Cookies?
Definitely! Using a mini muffin tin reduces baking time to around 12–15 minutes and makes for adorable snacks or party bites.
Why should I invert the cookies after baking?
Inverting reveals the gooey caramelized pineapple and cherry topping, which gives the cookies their signature appearance and delightful texture contrast between the crispy bottom and tender cookie.
Can I add spices to the recipe?
Yes! Adding a pinch of cinnamon or nutmeg into the topping mix adds warmth and depth that complements the pineapple beautifully.
Final Thoughts
There is something truly special about this Pineapple Upside-Down Cookies Recipe that makes every bite feel like a little celebration of tropical sunshine. Whether you’re baking for a casual family snack or a special occasion dessert, these cookies bring unbeatable flavor, charming presentation, and moments of pure joy. I can’t wait for you to try them and see how quickly they become a beloved staple in your baking repertoire!
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
Pineapple Upside-Down Cookies combine the classic flavors of pineapple and maraschino cherries with a soft, buttery cookie base in an easy-to-make, bite-sized treat. Featuring a caramelized brown sugar and butter topping with a juicy pineapple center, these cookies offer a delightful tropical twist on traditional upside-down desserts.
Ingredients
For the Topping:
- ½ cup light brown sugar (for topping)
- 2 tablespoons unsalted butter (melted)
- 12 maraschino cherries (halved)
- ½ cup crushed pineapple (drained)
For the 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
- ¼ cup pineapple juice
Instructions
- Preheat and prepare muffin tin: Preheat the oven to 350°F (175°C) and lightly grease or line a muffin tin with paper liners to prevent sticking.
- Make the topping mixture: In a small bowl, combine ½ cup light brown sugar with melted butter until well mixed. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup.
- Add fruit to topping: Place half a maraschino cherry in the center of each muffin cup on top of the sugar-butter mixture, then add a small spoonful of well-drained crushed pineapple over the cherry.
- Cream the butter and sugars: In a large bowl, cream together the softened butter, 1 cup light brown sugar, and ½ cup granulated sugar using a mixer until light and fluffy.
- Add eggs and vanilla: Beat in eggs one at a time, ensuring each is fully incorporated before adding the next, then mix in the vanilla extract.
- Combine dry ingredients: In a separate bowl, whisk together all-purpose flour, baking powder, baking soda, and salt to evenly distribute the leavening agents.
- Mix wet and dry ingredients: Gradually add the dry ingredients to the wet mixture, alternating with pineapple juice, mixing just until combined to avoid overworking the dough.
- Fill muffin cups: Spoon the cookie dough over the pineapple topping mixture in each muffin cup, filling about three-quarters full to allow room for rising.
- Bake the cookies: Place the muffin tin in the preheated oven and bake for 18–22 minutes or until the cookies are golden brown and a toothpick inserted in the center comes out clean.
- Cool and invert: Let the cookies cool in the tin for 5 minutes. Then carefully invert the tin onto a wire rack to release the cookies and reveal the pineapple upside-down topping. Serve warm or at room temperature.
Notes
- For added flavor, sprinkle a pinch of cinnamon into the brown sugar topping mixture.
- Ensure the crushed pineapple is well drained to prevent soggy cookies.
- These cookies can also be made in mini muffin tins for bite-sized treats, adjusting baking time accordingly.
