If you are searching for a delightful twist on a classic treat, the Pineapple Upside-Down Cookies Recipe brings all the charm of the traditional cake into the perfect bite-sized form. These cookies combine the irresistibly buttery, caramelized topping with juicy pineapple and bright maraschino cherries, all resting atop a tender, fluffy cookie base. The fusion of sweet and tangy flavors makes these cookies an unforgettable indulgence, perfect for impressing guests or brightening your own day with a tropical flair.
Ingredients You’ll Need
Gathering simple, pantry-friendly ingredients is the secret to pulling off this Pineapple Upside-Down Cookies Recipe flawlessly. Each component plays a vital role, whether it’s building the cookie’s tender crumb, adding rich caramel notes, or infusing vibrant fruity bursts.
- ½ cup unsalted butter (softened): Provides a creamy richness essential for a moist, flavorful cookie base.
- ¾ cup granulated sugar: Sweetens the dough while helping create a tender texture.
- 1 large egg: Binds ingredients together and adds structure.
- 1 tsp vanilla extract: Brings depth and aromatic warmth to the cookie dough.
- 1 ¼ cups all-purpose flour: The foundation of the dough, creating just the right balance of chewiness.
- ½ tsp baking powder: Adds a subtle lift, ensuring cookies aren’t dense.
- ¼ tsp salt: Enhances all flavors, balancing sweetness beautifully.
- ½ cup brown sugar (for topping): Delivers that classic caramelized topping that’s key to the upside-down style.
- 2 tbsp melted butter (for topping): Helps the brown sugar caramelize perfectly over the pineapple.
- Pineapple rings (1 small can, chopped): Adds juicy, tropical bursts that contrast wonderfully against the sweet base.
- Maraschino cherries (halved): Provide a vibrant pop of color and a festive, sweet finish.
How to Make Pineapple Upside-Down Cookies Recipe
Step 1: Prepare Your Oven and Baking Sheet
Start by preheating your oven to 350°F (175°C). This even heat is perfect for baking your cookies so they come out golden brown and perfectly cooked inside. Line a baking sheet with parchment paper—this prevents sticking and makes cleanup a breeze. Trust me, small steps like this make a big difference in the final bake.
Step 2: Cream Butter and Sugar
In a mixing bowl, beat together your softened unsalted butter and granulated sugar until the mixture turns light and fluffy. This process is the heart of your cookie dough, incorporating air to give your cookies a soft texture. Then, add your egg and vanilla extract, blending everything smoothly to ensure a harmonious batter.
Step 3: Combine Dry Ingredients and Mix
Whisk the all-purpose flour, baking powder, salt, and brown sugar together in a separate bowl to distribute everything evenly. Gradually add the dry mix to your wet ingredients, stirring just until combined. Overmixing can toughen your cookies, so aim for a gentle fold to keep the dough tender and light.
Step 4: Create the Caramelized Pineapple Base
Drizzle melted butter onto your lined baking sheet, then sprinkle the brown sugar uniformly over it. This creates that signature caramelized layer that melts into the pineapple’s sweetness. Arrange chopped pineapple pieces on top, placing halved maraschino cherries over them. This colorful layer will become the beautiful top of your cookies once baked.
Step 5: Assemble and Bake
Carefully scoop spoonfuls of cookie dough onto each pineapple piece, slightly covering the fruit but leaving the cherries visible for a vibrant look. Slide the baking sheet into your preheated oven and bake for 12 to 15 minutes or until the edges of the cookies turn a warm, golden brown. The aroma filling your kitchen at this point is absolutely irresistible.
Step 6: Cooling and Serving
Once baked, let the cookies cool slightly on the tray before transferring them to a wire rack. This allows the caramel to set without being too sticky, giving your Pineapple Upside-Down Cookies Recipe that perfect balance of tender cookie and luscious topping.
How to Serve Pineapple Upside-Down Cookies Recipe
Garnishes
Enhance your presentation by dusting the cooled cookies lightly with powdered sugar or adding a dollop of whipped cream on the side. A small mint leaf on top of each cookie can add a fresh pop of color and flavor, making these treats as delightful to look at as they are to eat.
Side Dishes
Pairing these cookies with a scoop of vanilla ice cream or a tropical fruit salad elevates the dessert experience. The creamy ice cream contrasts beautifully with the caramelized pineapple, while the fruit salad keeps the tropical vibe flowing and adds a refreshing balance.
Creative Ways to Present
For a fun twist, serve these cookies stacked on a dessert platter with assorted tropical accents like edible flowers or sliced kiwi. Alternatively, place individual cookies on colorful dessert plates alongside a drizzle of caramel sauce or a splash of rum syrup to amp up the decadence for special occasions.
Make Ahead and Storage
Storing Leftovers
Once completely cooled, store your pineapple upside-down cookies in an airtight container at room temperature. They will stay fresh for up to 3 days and maintain their tender crumb and juicy topping. Layer the cookies between parchment paper to prevent sticking.
Freezing
These cookies freeze beautifully if you want to enjoy them later. Arrange them in a single layer on a baking sheet to flash freeze before transferring to a freezer-safe container or bag. They will keep well for up to one month, allowing you to savor the tropical goodness whenever you like.
Reheating
To enjoy your cookies warm, simply reheat them in a preheated oven at 300°F (150°C) for about 5 minutes. This revives the gooey pineapple topping and refreshes the cookie’s softness. Avoid microwaving as it can make the texture less pleasant.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple adds a naturally brighter flavor and juicier texture. Just make sure to chop it into small pieces and pat it dry to avoid excess moisture that could affect the cookie dough consistency.
Is brown sugar necessary for the topping?
Yes, brown sugar is key for achieving that classic caramelization in the topping. Its molasses content creates the rich flavor and sticky texture that make these cookies stand out.
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 ensure your baking powder is gluten-free as well. The texture might be slightly different but still delicious!
What’s the best way to soften butter quickly?
To soften butter fast, cut it into small cubes and let it sit at room temperature for about 15 minutes. Alternatively, you can microwave it at very low power in short bursts, checking frequently to avoid melting.
Can I double the recipe?
You can double the ingredients easily! Just be sure to use larger baking sheets or multiple batches to avoid overcrowding, ensuring each cookie bakes evenly and beautifully.
Final Thoughts
I hope this Pineapple Upside-Down Cookies Recipe inspires you to blend a little tropical sunshine into your baking routine. The combination of buttery dough, caramelized brown sugar, juicy pineapple, and sweet cherries is simply magic. Once you try these cookies, they’ll become a cherished favorite to share at every gathering or savor on a quiet afternoon. Give them a try and watch how quickly they disappear!
Print
Pineapple Upside-Down Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Total Time: 30 minutes
- Yield: Approximately 24 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Pineapple Upside-Down Cookies combine the classic caramelized pineapple and cherry topping of the traditional cake with a soft, buttery cookie base. Perfectly golden and lightly sweet, these cookies offer a delightful tropical twist that’s easy to make and sure to impress.
Ingredients
Cookie Dough
- ½ cup unsalted butter, softened
- ¾ cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- 1 ¼ cups all-purpose flour
- ½ tsp baking powder
- ¼ tsp salt
Topping
- ½ cup brown sugar (for topping)
- 2 tbsp melted butter (for topping)
- 1 small can pineapple rings, chopped
- Maraschino cherries, halved
Instructions
- Preheat Oven and Prepare Pan: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking and ensure even baking.
- Cream Butter and Sugar: In a mixing bowl, beat the softened unsalted butter and granulated sugar together until the mixture is light, fluffy, and well combined. This helps incorporate air into the dough for a tender texture.
- Add Egg and Vanilla: Add the egg and vanilla extract to the butter-sugar mixture and mix until fully incorporated, creating a smooth batter.
- Mix Dry Ingredients: In a separate bowl, whisk together all-purpose flour, baking powder, salt, and brown sugar (for dough) to evenly distribute the leavening agents and keep the mixture uniform.
- Combine Dry and Wet Ingredients: Gradually add the dry ingredients into the wet mixture and mix just until combined to avoid overworking the dough, which can make cookies tough.
- Prepare Topping on Pan: Drizzle the melted butter onto the lined baking sheet, then sprinkle the brown sugar evenly over it. Arrange chopped pineapple pieces and top each with a halved maraschino cherry to create the classic upside-down effect.
- Assemble Cookies: Using a spoon or cookie scoop, place dollops of cookie dough on top of each pineapple and cherry piece on the baking sheet, spacing them evenly.
- Bake: Bake the cookies in the preheated oven for 12–15 minutes or until they turn golden brown around the edges and are set in the center.
- Cool and Serve: Allow the cookies to cool slightly on the baking sheet before removing. Serve warm or at room temperature to enjoy the caramelized topping and soft cookie base.
Notes
- Make sure the butter for the dough is softened to room temperature for easier creaming and better texture.
- Do not overmix the dough to keep the cookies tender and soft.
- You can substitute fresh pineapple chopped into small pieces if canned is not available.
- For a more intense flavor, try using dark brown sugar for the topping instead of light brown sugar.
- Store leftover cookies in an airtight container at room temperature for up to 3 days.
