If you adore the classic pineapple upside-down cake but crave something a little more portable and snack-friendly, then you are going to fall in love with this Pineapple Upside-Down Cookies Recipe. These delightful little treats capture all the tropical sweetness and cherry charm of the original dessert, but in perfectly sized, crispy-on-the-edges, soft-in-the-middle cookies baked right in a muffin tin. The combination of buttery brown sugar, juicy pineapple, and maraschino cherries creates a burst of flavor that feels like a warm, sunny day with every bite.
Ingredients You’ll Need
Gathering simple ingredients that pack a flavorful punch is the key to making these cookies shine. Each component plays a special role, from creating that signature caramelized bottom to adding moisture, texture, and an irresistible tropical twist.
- Unsalted butter (softened): Provides rich creaminess to the dough and the buttery base for that caramelized topping.
- Brown sugar (packed): Adds deep molasses notes essential for the signature upside-down flavor and caramelization.
- Granulated sugar: Balances sweetness and helps lighten the dough’s texture.
- Large egg: Binds the ingredients together and gives structure to the cookies.
- Vanilla extract: Enhances the sweetness with warm, comforting aroma and flavor.
- All-purpose flour: The base that creates a tender yet sturdy cookie dough.
- Baking soda: Leavens the cookies for just the right rise and softness.
- Salt: Balances the sweetness and enhances all the flavors.
- Crushed pineapple (drained): Brings juicy tropical sweetness and moisture without sogginess (drain well!).
- Pineapple juice (reserved): Adds moisture and intensifies pineapple flavor in the dough.
- Maraschino cherries (halved): Bright, sweet, and visually charming topping for each cookie.
- Additional brown sugar (for topping): Creates the glossy caramelized crust on the cookie bottoms.
- Unsalted butter (melted): Combines with the topping sugar to achieve that perfect sticky-sweet base.
How to Make Pineapple Upside-Down Cookies Recipe
Step 1: Prepare the Topping Base
Start by preheating your oven to 350°F (175°C) and greasing a standard muffin tin because this recipe relies on the muffin pan to create individual mini upside-down masterpieces. In a small bowl, mix together the 1/3 cup of brown sugar and melted butter until well combined. Then drop a teaspoon of this luscious mixture into the bottom of each muffin cup—it’s the foundation for that beautiful caramel-like crust.
Step 2: Add Pineapple and Cherries
Place one half of a maraschino cherry right in the center of each greased muffin cup atop the butter and sugar mixture. Next, spoon about a teaspoon of well-drained crushed pineapple on top of the cherry so that every cookie will have that juicy burst of tropical sweetness as they bake.
Step 3: Make the Cookie Dough
In a large mixing bowl, cream together the softened butter, brown sugar, and granulated sugar until the mixture is light and fluffy. This step is crucial because it traps air, resulting in tender, cakey cookies. Beat in the egg and vanilla extract until fully incorporated.
Step 4: Combine Dry Ingredients and Add to Wet Mix
In a separate bowl, whisk the flour, baking soda, and salt to evenly distribute the leavening agents. Gradually add the dry ingredients to the wet mixture, alternating with the reserved pineapple juice, mixing just until everything is combined. Overmixing can make cookies tough, so keep it gentle!
Step 5: Assemble and Bake
Drop about 2 tablespoons of cookie dough into each muffin cup on top of the pineapple and cherry layer, pressing gently to flatten slightly. Bake in the preheated oven for 14 to 16 minutes or until the cookies are golden brown and set. The kitchen will fill with the heavenly aromas of caramel, vanilla, and tropical pineapple—pure joy!
Step 6: Cool and Invert
Allow the cookies to cool in the muffin tin for about 5 minutes so the caramel topping can set slightly. Then carefully invert the tin onto a cooling rack, releasing the cookies to reveal their sunny pineapple upside-down tops. These cookies are best enjoyed warm, but they hold up beautifully at room temperature too.
How to Serve Pineapple Upside-Down Cookies Recipe
Garnishes
To jazz up these pineapple upside-down cookies at your next gathering, try sprinkling a bit of toasted coconut flakes or finely chopped macadamia nuts over the top for added tropical flair and a pleasant crunch. A light dusting of powdered sugar can also bring an elegant touch.
Side Dishes
Pineapple upside-down cookies pair wonderfully with a scoop of creamy vanilla ice cream or a dollop of whipped cream to balance the sweetness. For a more adult twist, serve alongside a glass of chilled sparkling wine or a fruity rum cocktail to complement those tropical notes.
Creative Ways to Present
Arrange these cookies on a platter with fresh pineapple slices and maraschino cherries for an eye-catching dessert spread. You can also serve them warm in little paper liners to make them perfect for parties or potlucks, making sure each guest gets their own mini tropical treat.
Make Ahead and Storage
Storing Leftovers
These cookies are best eaten fresh but will keep nicely in an airtight container at room temperature for up to 2 days. Make sure to store them in a single layer to prevent the delicate caramel tops from sticking together or losing their texture.
Freezing
If you want to prepare these cookies ahead or keep extras for later, they freeze beautifully. Place the cooled cookies in a single layer on a baking sheet, freeze until solid, then transfer to a freezer-safe container or zip-top bag. They should maintain their flavor and texture for up to 2 months.
Reheating
To bring frozen or stored pineapple upside-down cookies back to life, gently warm them in a 300°F oven for about 5 to 7 minutes. This will restore their soft texture and help the caramel topping regain that lovely stickiness. Avoid microwaving, which can make the cookie rubbery.
FAQs
Can I use fresh pineapple instead of canned crushed pineapple?
Absolutely! Fresh pineapple can add a brighter flavor, but be sure to finely chop and drain it very well to avoid sogginess. The key is removing excess juice to maintain the right cookie texture.
What if I don’t have maraschino cherries? Can I skip them?
The cherries add visual appeal and a burst of sweetness, but if you don’t have them, you can omit or substitute with another sweet fruit like a small piece of dried apricot. The cookies will still taste amazing.
Can I make this recipe gluten-free?
Yes! Use a 1-to-1 gluten-free baking flour blend with xanthan gum to replicate the texture of all-purpose flour. The cookies should turn out just as tender and flavorful.
Is there a vegan version of this Pineapple Upside-Down Cookies Recipe?
You can experiment with vegan butter and egg substitutes like flax eggs, but the texture and flavor might slightly differ. Using ripe bananas or applesauce can also add moisture, but it’s best to try a small batch first.
How do I know when the cookies are done baking?
Look for golden brown edges and a set top without jiggle. Baking times can vary slightly depending on your oven and muffin tin, so check at 14 minutes and adjust as needed for a perfect bake.
Final Thoughts
This Pineapple Upside-Down Cookies Recipe is a delightful way to capture all the warmth and sweetness of a classic dessert in a bite-sized treat. Whether you’re baking for your family, a potluck, or simply indulging your sweet tooth, these cookies never fail to surprise and satisfy. Give them a try and watch how quickly they disappear—trust me, you’ll want to make these charming cookies again and again!
Print
Pineapple Upside-Down Cookies Recipe
- Prep Time: 20 minutes
- Cook Time: 16 minutes
- Total Time: 36 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These Pineapple Upside-Down Cookies offer a delightful twist on the classic dessert, featuring a tender, buttery cookie base topped with sweet caramelized brown sugar, pineapple, and maraschino cherries. Baked in a muffin tin, they are perfectly portioned, combining a soft, moist interior with a sticky, fruity topping that makes them irresistible for any occasion.
Ingredients
For the Topping
- 1/3 cup brown sugar
- 2 tablespoons unsalted butter, melted
- 12 maraschino cherries, halved
- 1/2 cup crushed pineapple, drained
For the Cookies
- 1/2 cup unsalted butter, softened
- 1/2 cup brown sugar, packed
- 1/4 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
- 1/4 cup pineapple juice (reserved from draining crushed pineapple)
Instructions
- Prepare the muffin tin topping: Preheat your oven to 350°F (175°C) and grease a standard muffin tin thoroughly. In a small bowl, combine the 1/3 cup brown sugar with the melted butter. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup. Place a halved cherry in the center of each cup, then top with approximately 1 teaspoon of well-drained crushed pineapple. This creates the signature upside-down topping.
- Mix the cookie dough base: In a large mixing bowl, cream together the softened unsalted butter, 1/2 cup packed brown sugar, and 1/4 cup granulated sugar until the mixture is light and fluffy. This may take about 3 to 4 minutes with a mixer. Beat in the egg and vanilla extract until well incorporated.
- Combine dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to distribute the leavening agents evenly in the flour.
- Integrate wet and dry components: Gradually add the dry flour mixture to the wet ingredients, alternating with the reserved pineapple juice. Start and end with the dry ingredients, mixing just until combined to avoid overworking the dough, which could make the cookies tough.
- Assemble cookies in muffin tin: Drop 2 tablespoons of the cookie dough into each muffin cup over the pineapple topping. Gently press the dough down to flatten slightly, ensuring it spreads evenly during baking for a uniform cookie shape.
- Bake the cookies: Place the muffin tin in the preheated oven and bake for 14 to 16 minutes, or until the cookies are golden brown around the edges and set in the center.
- Cool and invert: Allow the cookies to cool in the muffin tin for about 5 minutes to set. Then carefully invert the tin onto a cooling rack so the pineapple and cherry topping is displayed on top. This step releases the cookies without breaking the caramelized topping layer.
- Serve: Serve the pineapple upside-down cookies warm or at room temperature for the best flavor and texture. They make a perfect dessert or sweet snack.
Notes
- Ensure the crushed pineapple is very well drained to prevent soggy cookies.
- For best results, enjoy these cookies the same day they are made as the topping can become sticky over time.
- Store any leftovers in an airtight container at room temperature for up to 2 days.
- You can substitute maraschino cherries with fresh cherries or other fruit pieces if desired.
- Press the dough gently but firmly into the muffin cups to ensure even cooking and shape retention.
