If you’re looking for a treat that instantly sparks joy (and brings a little sunshine to your dessert table), let me introduce you to Pineapple Upside-Down Cookies. These darling mini desserts take everything you love about the retro classic—juicy pineapple, sweet cherries, and a buttery, brown sugar glaze—and transform it into a hand-held, shareable cookie creation. Gorgeous to look at and even more delightful to eat, you’ll want to make a double batch, because these cookies are pure happiness in every bite!

Pineapple Upside-Down Cookies Recipe - Recipe Image

Ingredients You’ll Need

The beauty of Pineapple Upside-Down Cookies is how approachable the ingredients are—each one delivers a pop of flavor, a bit of texture, or a gorgeous splash of color that makes these cookies so irresistible. With just a few pantry staples and a couple of fruity additions, you’re well on your way to something special.

Unsalted butter: Essential for that rich, decadent cookie base and perfect for browning up the tops when the cookies are inverted.
Brown sugar: Brings warmth and deep caramel notes to the topping and the dough itself—don’t skimp on packing it for full flavor!
Granulated sugar: Adds just the right touch of classic cookie sweetness, balancing out the tanginess of the fruit.
Large eggs: Help bind the dough, giving your cookies that perfect chewy texture.
Vanilla extract: A splash of vanilla rounds out all the flavors and provides a delicious, cozy aroma.
All-purpose flour: The backbone of the cookies—gives them structure without making them heavy.
Baking powder and baking soda: Lifts the cookies for a light, cake-like crumb that pairs wonderfully with the juicy fruit.
Salt: Just a pinch amplifies every other flavor—it’s tiny but mighty!
Pineapple juice: Incorporates tropical sweetness right into the dough itself while keeping everything moist.
Crushed pineapple: Well-drained crushed pineapple brings zingy bursts of flavor to each cookie (don’t forget to drain it well for best results).
Maraschino cherries: For that nostalgic pop of red and an extra touch of retro charm—halve them for the perfect fit.
Chopped pecans (optional): Lend a bit of crunch and toasty flavor if you’re in the mood for a little nutty contrast.

How to Make Pineapple Upside-Down Cookies

Step 1: Prepare Your Muffin Tins

Begin by preheating your oven to 350°F (175°C). Either line your muffin tins with paper liners or lightly grease them to guarantee those gorgeous cookies slide out effortlessly once they’re baked. A little prep here makes life much easier when it’s time to invert your cookies!

Step 2: Build That Signature Pineapple Base

In a medium bowl, mix together 1/2 cup of the brown sugar with 1/4 cup of the softened butter until you have a caramel-like paste. Drop a small spoonful of this mixture into the bottom of each muffin cup. Press half a maraschino cherry right in the center, top with a teaspoon of well-drained crushed pineapple, and sprinkle a few pecans on top (if using). This step ensures every Pineapple Upside-Down Cookie has a show-stopping presentation—and that sweet, fruity bottom layer everyone adores.

Step 3: Cream the Butter and Sugars

In a large bowl, cream together the remaining softened butter with the granulated sugar and the rest of the brown sugar. Beat them together until light, fluffy, and pale in color. This aerates the mixture, creating a soft cookie crumb that feels almost cake-like, but with all the convenience of a cookie.

Step 4: Add Eggs and Vanilla Extract

Crack in the eggs one at a time, mixing until each is completely integrated before adding the next. Follow that with the vanilla extract for that unmistakable cozy aroma. Take your time here to ensure the batter stays silky and well combined.

Step 5: Whisk Dry Ingredients and Combine

In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. This keeps your leaveners evenly distributed. Add the dry ingredients to the butter mixture in batches, alternating with the pineapple juice. Stir gently, mixing until just combined—overmixing can make your cookies tough, and we want every bite to be cloud-soft.

Step 6: Assemble and Bake

Spoon the finished cookie dough right over your pineapple topping in each muffin cup, filling about three-quarters full (they’ll puff up beautifully). Slide the tray into the oven and bake for 18 to 22 minutes, or until golden brown and a toothpick comes out clean. The aroma will make your kitchen feel like a tropical getaway!

Step 7: Invert and Cool

Once baked, give the cookies about five minutes to cool in the pan. Then, run a small knife around the edge of each one and carefully invert them onto a wire rack. This is the magical moment—your Pineapple Upside-Down Cookies will reveal their glistening tops, complete with pineapple, cherry, and a hint of nutty crunch. Let them cool fully before savoring (if you can wait that long!).

How to Serve Pineapple Upside-Down Cookies

Garnishes

A light dusting of powdered sugar, a drizzle of vanilla glaze, or even a sprinkle of toasted coconut can take Pineapple Upside-Down Cookies from delightful to show-stopping. If you’re feeling extra tropical, a tiny wedge of fresh pineapple perched on top makes for an irresistible bite.

Side Dishes

Pair these cookies with a scoop of vanilla ice cream, coconut gelato, or a swirl of lightly sweetened whipped cream. For a coffee-hour treat, they’re a natural match with a cup of strong black coffee or an iced coconut latte—you just can’t go wrong!

Creative Ways to Present

Arrange Pineapple Upside-Down Cookies on a tiered cake stand for a fun tea party vibe, or wrap them in cellophane for a cheerful homemade gift. If you’re serving at a party, channel your inner retro hostess—stick a tiny cocktail umbrella into each cookie for a playful, unforgettable dessert platter.

Make Ahead and Storage

Storing Leftovers

To keep Pineapple Upside-Down Cookies at their best, store them in an airtight container at room temperature for up to 2 days. If your kitchen is particularly warm or humid, pop them in the fridge—just make sure they’re fully cooled first to prevent moisture buildup and sogginess.

Freezing

These cookies freeze surprisingly well! Once cooled, layer Pineapple Upside-Down Cookies between sheets of parchment and seal in a freezer-safe container. They’ll keep beautifully for up to 2 months. Let them thaw at room temperature when you need a taste of the tropics.

Reheating

If you prefer your Pineapple Upside-Down Cookies slightly warm (who doesn’t?), just reheat them in a 300°F oven for about 5 minutes, or microwave for 10-15 seconds. The fruity topping gets nice and glossy again, just like fresh-baked.

FAQs

Can I make Pineapple Upside-Down Cookies nut-free?

Absolutely! Simply skip the pecans in the recipe, and your cookies will still have all that fabulous flavor and texture, free of any nutty crunch. They’re just as delicious for everyone to enjoy.

What type Dessert

Crushed pineapple is the best option because it distributes evenly and gives every cookie a juicy burst of fruit. Be sure to drain it thoroughly so your Pineapple Upside-Down Cookies don’t turn out soggy.

Can I use fresh pineapple instead of canned?

Sure! Just chop it finely and drain any excess juice. Canned crushed pineapple is quick and convenient, but fresh adds a bolder flavor, especially when pineapples are in season.

Why did my cookies stick to the muffin tin?

Sticking can happen if you don’t line or grease the muffin cups well, or if you try to invert the cookies before they’ve cooled a bit. Let them cool for about 5 minutes after baking for a flawless, mess-free release.

Can I double this recipe for a crowd?

It’s easy to double! Just prep two muffin pans and mix up a larger batch—you’ll have a bounty of Pineapple Upside-Down Cookies to share at your next potluck or family gathering.

Final Thoughts

If you’ve never baked Pineapple Upside-Down Cookies before, now’s the time to give it a go—a little bit nostalgic, a whole lot joyful, and completely irresistible. Trust me, your kitchen (and your lucky taste-testers) will thank you for spreading a little sunshine, one cookie at a time!

Pineapple Upside-Down Cookies Recipe

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4.6 from 29 reviews

Author: admin
Total Time: 45 minutes
Yield: 18 cookies 1x
Diet: Vegetarian

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Description

These Pineapple Upside-Down Cookies are a delightful twist on the classic cake. With a buttery cookie base topped with sweet pineapple, cherries, and optional pecans, these mini treats are bursting with tropical flavors.

Ingredients

Scale

Cookies:

1 cup unsalted butter (softened)
1 cup brown sugar (packed)
1/2 cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
2 1/2 cups all-purpose flour
1 teaspoon baking powder
1/2 teaspoon baking soda
1/4 teaspoon salt
1/4 cup pineapple juice

Toppings:

1 cup crushed pineapple (well-drained)
1/2 cup maraschino cherries (halved)
1/2 cup chopped pecans (optional)

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Instructions

Preheat the oven: Preheat the oven to 350°F (175°C) and prepare muffin tins.
Prepare the base: Mix brown sugar and butter in a bowl, place in muffin cups, add cherries, pineapple, and pecans.
Make the dough: Cream butter and sugars, add eggs and vanilla. Combine dry ingredients and pineapple juice, then mix into the wet ingredients.
Fill the cups: Spoon cookie dough over the pineapple mixture in each cup.
Bake: Bake for 18–22 minutes until golden brown.
Cool and serve: Let cool in the pan, then invert onto a wire rack to cool completely.