Name: A Fun Twist on a Classic Dessert Recipe
Prep time: 20 min
Cook time: 15 min
Total time: 35 min
Cuisine: American
Ingredients: Unsalted Butter (½ cup, softened); Granulated Sugar (¾ cup); Large Egg (1); Vanilla Extract (1 tsp); All-Purpose Flour (1 ¼ cups); Baking Powder (½ tsp); Salt (¼ tsp); Brown Sugar (½ cup); Melted Butter (2 tbsp); Pineapple Rings (1 small can, cut into smaller pieces); Maraschino Cherries (halved)

Jump to Recipe

If you’re looking for a playful and crowd-pleasing treat that will take you right back to childhood, Pineapple Upside-Down Cookies are your new best friend. This recipe is truly A Fun Twist on a Classic Dessert, pairing buttery, soft cookies with a gorgeously gooey pineapple and cherry topping. You get all the nostalgia of grandma’s upside-down cake, but in cute, hand-held cookie form—ready for potlucks, parties, or just a sweet afternoon escape. Once you take a bite, you’ll realize these cookies are destined to become a repeat favorite in your baking repertoire.

A Fun Twist on a Classic Dessert Recipe - Recipe Image

Ingredients You’ll Need

Don’t you just love when a recipe feels effortlessly special? The best thing about these Pineapple Upside-Down Cookies is how simple the ingredient list is, while each component makes a big difference to the final flavor, texture, or color. Here’s everything you’ll need to make A Fun Twist on a Classic Dessert:

Unsalted Butter (½ cup, softened): Essential for that rich, classic cookie taste; if you only have salted, just reduce the added salt in the recipe.
Granulated Sugar (¾ cup): Gives the cookies sweetness and helps maintain a soft bite; swap in brown sugar for deeper caramel notes if you like.
Large Egg (1): Binds the ingredients and adds moisture, but feel free to use a flax egg for an egg-free version.
Vanilla Extract (1 tsp): Adopts a supporting role, enhancing the overall aroma and taste.
All-Purpose Flour (1 ¼ cups): The backbone of the cookie; use a 1:1 gluten-free blend if needed—no one misses out!
Baking Powder (½ tsp): Adds just enough lift to keep the cookies light but not cakey.
Salt (¼ tsp): Brings all the sweetness and flavors into sharp, delicious focus.
Brown Sugar (½ cup): Caramelizes during baking for that signature “upside-down” sticky topping.
Melted Butter (2 tbsp): Helps the brown sugar bubble into a syrupy, irresistible layer.
Pineapple Rings (1 small can, cut into smaller pieces): The star of the show; fresh pineapple also works—just dice it up for even baking.
Maraschino Cherries (halved): Classic, bright, and sweet, but fresh cherries or dried cranberries are lovely alternatives.

How to Make A Fun Twist on a Classic Dessert

Step 1: Prepare the Cookie Dough

This is where our cookies start to get their incredible softness. Preheat your oven to 350°F (175°C) and line a baking sheet with parchment or a silicone mat. In a large mixing bowl, cream together the softened butter and granulated sugar—an electric mixer speeds things up, but a sturdy whisk and some elbow grease do the trick, too. When you see the mixture become pale and fluffy, add your egg and vanilla. Stir or beat until smooth and glossy. In a separate bowl, whisk your flour, baking powder, and salt. Gradually incorporate the dry mix into the wet ingredients, stirring just until a soft cookie dough forms. Over-mixing is the enemy, so stop as soon as everything is combined.

Step 2: Prepare the Topping

This caramelized layer is what transforms these from everyday cookies to A Fun Twist on a Classic Dessert. Stir the melted butter with brown sugar in a small bowl until smooth and spreadable. Drop teaspoon-sized portions onto your lined baking sheet, making sure to give them space to spread. This is the little secret behind that sticky, shiny, classic upside-down finish.

Step 3: Assemble the Cookies

Now comes the fun, fruity part! Place a small piece of pineapple right in the center of each brown sugar puddle, then pop a maraschino cherry half in the middle of the pineapple—this gives every cookie that signature dessert look. Scoop about 1 ½ tablespoons of your cookie dough, flatten it lightly in your hands, and gently blanket it over the pineapple-cherry base. Take care to seal the edges, tucking all that deliciousness underneath.

Step 4: Bake the Cookies

Slide your tray into the preheated oven and bake for 12-15 minutes, watching for the edges to turn golden. The aroma will be amazing! After baking, let the cookies cool on the tray for five minutes—this helps the sticky topping set—then use a spatula to gently transfer them to a wire rack to finish cooling. Resist flipping them right away; patience is the key for perfect tops.

Step 5: Serve and Enjoy

Once your cookies are completely cool, flip them upside-down and marvel at the glossy pineapple-cherry tops. The big reveal is half the fun! Serve these at parties, as a lunchtime treat, or whenever you want A Fun Twist on a Classic Dessert to make someone’s day a little brighter.

How to Serve A Fun Twist on a Classic Dessert

Garnishes

For a real showstopper, dust your cookies with a little powdered sugar or finish with a light drizzle of melted white chocolate. You can also sprinkle toasted coconut or a few crushed pistachios over the top, which not only adds flavor but makes the cookies feel extra festive.

Side Dishes

Pair your Pineapple Upside-Down Cookies with tropical fruit salad for an all-out island vibe, or offer them alongside a scoop of vanilla or coconut ice cream to echo the flavors of A Fun Twist on a Classic Dessert. If you’re feeling creative, a creamy coffee or tea balances the sweetness for an afternoon treat.

Creative Ways to Present

If you want to turn these treats into an event, serve them individually in cupcake liners, or stack them in a pretty jar tied with a ribbon as a homemade edible gift. For party platters, alternate them with chocolate chip or sugar cookies for a pop of color—and a sure conversation starter when someone discovers A Fun Twist on a Classic Dessert.

Make Ahead and Storage

Storing Leftovers

To keep the cookies moist and flavorful, store them in an airtight container at room temperature for up to three days. If your kitchen tends to run warm or humid, pop the container in the refrigerator to keep the fruit topping fresh and vibrant. Bring chilled cookies to room temperature just before serving for best flavor.

Freezing

Pineapple Upside-Down Cookies freeze surprisingly well! For long-term storage, arrange cooled cookies in a single layer on a baking sheet and freeze until solid. Then transfer to a zip-top bag or airtight container with parchment between layers. They’ll keep in the freezer for up to two months—ideal for prepping A Fun Twist on a Classic Dessert ahead of party season.

Reheating

When you’re craving a warm cookie, just pop one in the microwave for 10-15 seconds to revive the gooey, caramel topping. Or, for a just-baked feel, warm cookies in a low (300°F) oven for about five minutes. Be sure to let them cool briefly before biting in—the topping can get deliciously hot!

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple works beautifully in this recipe. Just cut it into small tidbits so each cookie gets a tender, sweet bite that bakes evenly. If using fresh pineapple, make sure to pat it dry with paper towels to prevent the topping from getting too watery.

Can I make these gluten-free?

Yes, you can substitute a high-quality 1:1 gluten-free flour blend in place of the all-purpose flour. The cookies will still be soft and delicious, so everyone can enjoy A Fun Twist on a Classic Dessert!

What’s the secret to getting the caramel topping just right?

The key is to mix your brown sugar and melted butter thoroughly for a smooth, spreadable base, and give the cookies room on the baking sheet. This allows the sugars to bubble and caramelize as they bake—creating that signature upside-down finish without running everywhere.

How do I keep the cookies from sticking to the parchment or pan?

Parchment paper or a silicone mat is essential in this recipe. The topping is sticky by nature, so it’s best to cool the cookies slightly before removing them. If they do stick a bit, use a thin spatula and gentle pressure to release them.

Can I double the recipe for a party?

Go for it! This recipe easily doubles or triples. Just be sure to bake the cookies in batches so the caramel topping has enough space to set on each cookie—you’ll be amazed at how quickly A Fun Twist on a Classic Dessert disappears at gatherings!

Final Thoughts

There’s just something joyful about transforming a beloved cake into a bite-sized treat, and these Pineapple Upside-Down Cookies truly are A Fun Twist on a Classic Dessert. Whether you’re baking for family, sharing with friends, or just treating yourself to something delightfully new, you owe it to yourself to give these cookies a try. Happy baking!

A Fun Twist on a Classic Dessert Recipe

★★★★★

4.8 from 19 reviews

Author: lina
Total Time: 35 minutes
Yield: Makes about 12 cookies
Diet: Vegetarian

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Description

These Pineapple Upside-Down Cookies are a delightful twist on the classic dessert, featuring a soft, buttery cookie base topped with caramelized brown sugar, tropical pineapple pieces, and sweet maraschino cherries. Perfect for a fun and flavorful treat!

Instructions

Prepare the Cookie Dough Preheat the oven to 350°F (175°C) and line a baking sheet. Cream butter and sugar, add egg and vanilla. Combine dry ingredients, then mix into wet mixture.
Prepare the Topping Mix melted butter and brown sugar. Spoon onto baking sheet.
Assemble the Cookies Place pineapple and cherry on brown sugar base, top with cookie dough.
Bake the Cookies Bake for 12-15 minutes until golden. Cool before transferring.
Serve and Enjoy Flip cookies upside-down and enjoy!

Prep Time: 20 minutes
Cook Time: 15 minutes
Category: Dessert
Method: Baking
Cuisine: American