If sunshine could be baked into a cookie, it would taste exactly like these Pineapple Upside Sugar Cookies. 🍍🍪 Bright, buttery, and bursting with tropical sweetness, these cookies take the charm of an old-fashioned pineapple upside-down cake and shrink it into bite-sized perfection.
Every cookie features a golden sugar-butter base that caramelizes just enough to give you that deliciously chewy edge, topped with crushed pineapple for a juicy pop of flavor and—if you’re feeling fancy—a maraschino cherry right in the center for that classic retro look. ✨
They’re a breeze to make, bake up in just 15 minutes, and are perfect for sharing (though you might not want to). Whether you’re dreaming of island breezes or just need a cheerful pick-me-up, these cookies will instantly transport you to your happy place. 🌞
Why You’ll Fall in Love with These Cookies
Sunshine in Every Bite
These cookies are pure joy in dessert form—soft, chewy sugar cookies meet the tropical tang of pineapple. The brown sugar caramelizes as they bake, creating that irresistible sticky-sweet layer that perfectly contrasts the buttery dough.
They’re like mini pineapple upside-down cakes but easier, faster, and totally portable. The pineapple adds natural sweetness and keeps the cookies moist for days, while the vanilla brings everything together with a comforting warmth.
Perfect for Parties, Gifts, or Everyday Indulgence
These cookies don’t just taste good—they look gorgeous, too! With their glistening pineapple tops and cherry centers, they’re the kind of dessert that catches everyone’s eye at bake sales, potlucks, and parties.
They also make perfect edible gifts—stack a few in a pretty box or jar, and you’ve got a homemade treat that feels personal and tropical all at once. Whether it’s a rainy afternoon bake or a summer picnic dessert, Pineapple Upside Sugar Cookies fit every occasion.
Ingredients You’ll Need
The Cookie Dough Base
- ½ cup unsalted butter, softened – Adds richness and structure to the cookies.
- ¾ cup granulated sugar – For sweetness and that classic sugar cookie flavor.
- 1 large egg – Binds everything together and keeps the cookies soft.
- 1 teaspoon vanilla extract – Adds aroma and depth.
- 1½ cups all-purpose flour – The perfect balance for chewy and tender cookies.
- ½ teaspoon baking powder – Gives a subtle lift.
- ¼ teaspoon salt – Balances sweetness and enhances flavor.
The Pineapple Topping and Garnish
- ½ cup crushed pineapple, well-drained – The star of the show! Adds fruity brightness and moisture.
- ¼ cup packed brown sugar – Creates that signature upside-down caramel layer.
- 1 tablespoon unsalted butter, melted – Helps the brown sugar caramelize perfectly.
- Maraschino cherries, halved (optional) – A pop of color and classic finishing touch.
Simple pantry staples come together to make something extraordinary—proof that great baking doesn’t need fancy ingredients.
Step-by-Step Instructions to Make Pineapple Upside Sugar Cookies
Step 1 – Preheat and Prep Your Baking Sheet
Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper. This prevents sticking and ensures the cookies bake evenly.
While the oven heats, take a moment to drain your crushed pineapple thoroughly. Press it gently with paper towels to remove excess liquid—this small step makes a big difference in getting the perfect texture.
Step 2 – Cream Butter and Sugar to Fluffy Perfection
In a mixing bowl, beat together the softened butter and granulated sugar until light and fluffy—about 2 to 3 minutes. This step is key for achieving that soft, tender crumb. The creamed butter traps air, which expands during baking and helps your cookies rise just right.
Once fluffy, beat in the egg and vanilla extract until smooth and fully combined. The batter should smell rich and buttery with a hint of tropical sweetness.
Step 3 – Mix in the Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, and salt. Slowly add this dry mixture to your wet ingredients, mixing just until combined. Don’t overmix—it can make the cookies tough instead of tender.
You’ll end up with a soft dough that’s slightly sticky but easy to handle. If it feels too wet, you can chill it in the fridge for 10–15 minutes before baking.
Step 4 – Fold in the Pineapple
Now for the tropical twist! Gently fold in the well-drained crushed pineapple using a spatula. Stir just enough to distribute it evenly throughout the dough.
The pineapple adds bursts of sweetness and keeps the cookies delightfully moist. You’ll notice the dough becoming slightly softer—this is normal and part of what gives the cookies their melt-in-your-mouth texture.
Step 5 – Create the Upside-Down Sugar Layer
Here’s the magic part! On your prepared baking sheet, sprinkle a small circle of brown sugar where each cookie will sit (about a teaspoon per cookie). Then drizzle a little melted butter over the sugar.
As the cookies bake, this mixture caramelizes beautifully, forming that golden, sticky-sweet layer reminiscent of pineapple upside-down cake.
Step 6 – Scoop, Shape, and Add Cherries
Using a cookie scoop or tablespoon, drop spoonfuls of dough directly over the brown sugar-butter circles. Gently flatten each mound slightly with your fingers or the back of a spoon.
If you’re using maraschino cherries, press half a cherry gently into the center of each cookie for that signature look. It’s optional—but highly recommended for that pop of color and nostalgia!
Step 7 – Bake to Golden Bliss
Bake in the preheated oven for 12–15 minutes, or until the edges are golden brown and the tops look just set. The smell? Pure paradise—sweet, buttery, and warm with pineapple perfume filling your kitchen.
Remove from the oven and let them cool on the baking sheet for 5 minutes before transferring to a wire rack. This short rest helps the caramelized bottoms firm up perfectly.
Step 8 – Cool, Flip, and Enjoy
You can serve these cookies as-is, or for the full “upside-down” effect, carefully flip them once cooled slightly. The golden brown sugar and pineapple topping will glisten beautifully on top.
Each bite is chewy, buttery, and bursting with tropical flavor—like a mini vacation for your taste buds. 🍍☀️
Tips for Perfect Pineapple Upside Sugar Cookies
Drain the Pineapple Thoroughly
This is the most important tip for success. Pineapple is naturally juicy, and too much moisture can make your dough heavy or cause your cookies to spread too much.
After opening the can, pour the crushed pineapple into a fine mesh strainer and press gently with the back of a spoon or a paper towel to remove excess liquid. You’ll want it to be damp, not dripping wet. This keeps your dough perfectly balanced and ensures your cookies bake up soft and chewy—not soggy.
Chill the Dough for Better Texture
If your dough feels soft or sticky, pop it in the refrigerator for 15–20 minutes before baking. This helps solidify the butter and makes the dough easier to handle.
Chilled dough also prevents over-spreading, giving your cookies that perfect bakery-style round shape. Plus, it allows the flavors to meld together beautifully, enhancing that tropical pineapple aroma.
Use the Right Amount of Sugar Topping
When sprinkling the brown sugar on your parchment paper, don’t overdo it. About a teaspoon per cookie is ideal—just enough to caramelize without turning into a sticky mess.
Too much can make the bottoms burn or cause the cookies to fuse together. A light touch gives you that golden, slightly crisp layer that contrasts perfectly with the soft interior.
The Magic of Pineapple in Baking
A Natural Sweetener and Moisture-Booster
Pineapple isn’t just for piña coladas—it’s a baker’s secret weapon! Its natural sweetness allows you to cut down on refined sugar while keeping your desserts irresistibly moist.
Crushed pineapple infuses cookies with a juicy tenderness that lasts for days, making these treats perfect for baking ahead. Plus, it’s packed with vitamin C and manganese, adding a tiny hint of nutritional value to your indulgence (we’ll take it!).
Tropical Flavor That Elevates Simplicity
What’s special about pineapple is how it transforms a simple cookie into something exotic and memorable. The bright, tangy notes contrast beautifully with the buttery richness of sugar cookie dough.
Each bite tastes like a sunny vacation, a balance of warmth and freshness that instantly uplifts your mood. Even if it’s snowing outside, one bite will make you feel like you’re lounging on a beach somewhere, toes in the sand.
Pineapple Upside Sugar Cookies
- Prep Time: 15 minutes
- Total Time: 30 minutes
- Category: 🍪 Cookies / Tropical Desserts
Description
A tropical twist on a classic! 🌴 These Pineapple Upside Sugar Cookies are soft, buttery, and bursting with pineapple sweetness — topped with a hint of coconut and a cherry on top for that nostalgic island vibe. Perfect for summer gatherings or anytime you crave something bright and cheerful! 🌞🍒
Ingredients
1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 ½ cups all-purpose flour
½ teaspoon baking powder
¼ teaspoon salt
½ cup crushed pineapple, drained
½ cup brown sugar
¼ cup unsweetened shredded coconut
Maraschino cherries (optional, for garnish)
Instructions
Preheat the Oven (5 minutes) 🔥
Preheat oven to 350°F (175°C). Line baking sheets with parchment paper and set aside.Cream Butter & Sugar (5 minutes) 🧈
In a large bowl, beat butter and granulated sugar until light and fluffy.Mix Wet Ingredients (3 minutes) 🥚
Add the egg and vanilla extract; mix until smooth and creamy.Combine Dry Ingredients (5 minutes) 🧂
In a separate bowl, whisk together flour, baking powder, and salt. Gradually add to the wet mixture until just combined.Add the Pineapple & Coconut (3 minutes) 🍍
Gently fold in the drained crushed pineapple and shredded coconut until evenly distributed.Prepare the Sugar Coating (2 minutes) 🍯
Mix brown sugar with a small pinch of flour in a bowl to help prevent spreading.Shape & Roll (8 minutes) ✋
Scoop tablespoon-sized portions of dough, roll into balls, and coat each one in the brown sugar mixture. Place on baking sheets 2 inches apart.Flatten & Garnish (2 minutes) 🍒
Press each cookie slightly with your palm or the bottom of a glass. Add a maraschino cherry in the center if desired.
Bake & Cool (15 minutes) 🍪
Bake for 12–15 minutes, or until edges are golden. Let cookies cool on the baking sheet for 5 minutes before transferring to a wire rack.
Notes
These cookies are a delightful mix of buttery sugar cookie texture and tropical pineapple flavor. 🍍
Make sure to drain the crushed pineapple well — too much moisture can make the dough sticky.
The maraschino cherry topping adds both color and a fun retro touch. 🍒
For extra flavor, try toasting the coconut before adding it to the dough.
Perfect for summer parties, bake sales, or holiday cookie swaps with a tropical twist! 🌴✨
Nutrition
- Serving Size: 24 cookies
- Calories: 180 kcal
Healthier Variations to Try
Lightened-Up Pineapple Cookies
If you’re looking to enjoy these cookies with a little less guilt, you can make a few small swaps that keep the flavor but trim down the calories:
- Replace half the butter with unsweetened applesauce.
- Use coconut sugar or monk fruit sweetener instead of white sugar.
- Try whole-wheat pastry flour for extra fiber.
You’ll still get that buttery pineapple goodness, just with a slightly lighter texture and a wholesome twist.
Gluten-Free or Vegan Adaptations
Want to make them suitable for all diets? No problem!
For gluten-free cookies, substitute a 1:1 gluten-free all-purpose baking flour blend. Just be sure it includes xanthan gum for structure.
To make them vegan, use plant-based butter and replace the egg with a flax egg (1 tablespoon ground flaxseed + 2.5 tablespoons warm water).
The result? Still chewy, still sweet, and still full of tropical sunshine.
Add Oats or Coconut for Texture and Nutrition
Want to make them even more irresistible? Add ¼ cup of shredded coconut or quick oats to your dough. The coconut brings a chewy texture and enhances that island flavor, while oats add a heartier bite and make the cookies more filling.
For extra flair, sprinkle toasted coconut flakes on top after baking—it’s like a mini vacation in cookie form!
How to Serve and Enjoy These Cookies
Warm vs. Room Temperature – The Great Debate
Here’s the truth: these cookies are divine either way. Fresh from the oven, they’re soft, gooey, and melt-in-your-mouth delicious with that caramelized pineapple glaze still warm.
Once cooled, they develop a delightful chewiness, and the flavors deepen—perfect for pairing with a cup of tea or coffee.
If you can’t decide, try one warm and one later (for, you know, “research” purposes 😉). Either way, you win.
Pairing Ideas – Drinks and Desserts
These cookies are versatile enough to enjoy on their own, but pairing them with the right drink can take the experience up a notch. Try these combinations:
- Morning treat: A hot latte or iced coffee with a splash of coconut milk.
- Afternoon snack: Pair with pineapple iced tea or lemonade for a refreshing combo.
- Dessert indulgence: Serve with a scoop of vanilla ice cream or drizzle a little caramel sauce over the top.
For extra flair at parties, serve them alongside tropical fruit skewers or a piña colada mocktail!
Recipes you may like also :
Easy 3 Ingredient Pineapple Ice Cream
Pineapple Pecan Cream Cheese Pound Cake
Mini Pineapple Upside Down Cheesecakes
How to Store and Reheat Pineapple Upside Sugar Cookies
Keeping Them Soft and Fresh
Store completely cooled cookies in an airtight container at room temperature for up to 4 days. If you live in a humid area, place a small piece of bread inside the container to help maintain softness (the bread absorbs excess moisture).
Want to keep that just-baked flavor? Warm them in the microwave for 5–7 seconds before serving—just enough to soften the brown sugar and bring back that heavenly aroma.
Freezing for Later Cravings
These cookies freeze beautifully! Once cooled, layer them between sheets of parchment paper in an airtight freezer container or bag. They’ll stay fresh for up to 2 months.
To enjoy later, thaw them at room temperature for 20–30 minutes or pop them in the oven at 300°F (150°C) for 5 minutes to revive that fresh-baked magic.
Perfect for when you need a tropical pick-me-up on a cold day.
Fun Flavor Variations
Coconut-Pineapple Paradise Cookies
Add ½ cup of shredded coconut to your dough for an extra tropical twist. The coconut toasts as the cookies bake, adding depth and a hint of crunch that pairs beautifully with the caramelized pineapple.
Pineapple Upside Caramel Cookies
Want even more decadence? Replace the brown sugar-butter base with a drizzle of caramel sauce before adding the dough. It melts into the cookies as they bake, creating gooey caramel-pineapple pockets that taste straight out of a dessert dream.
Cherry Swirl Pineapple Cookies
Mix finely chopped maraschino cherries directly into the dough before baking. You’ll get cheerful red swirls throughout your cookies—fun, fruity, and gorgeous on any dessert table!
Why These Cookies Are So Loved
Simple, Stunning, and Deliciously Unique
These cookies combine simplicity with sophistication. The ingredients are basic, the steps are easy, yet the result looks and tastes bakery-worthy. Each bite is a blend of buttery sweetness and tropical freshness—a match made in dessert heaven.
Plus, they’re customizable. Whether you add coconut, caramel, or cherries, they’re impossible to mess up. Even beginner bakers can pull these off with confidence.
Nostalgic Comfort with a Tropical Twist
There’s something comforting about pineapple desserts—they bring back childhood memories of family gatherings and sunny vacations. These cookies capture that nostalgia while adding a fun, modern spin.
They’re cheerful, cozy, and oh-so-satisfying—the kind of dessert that brings smiles all around the table. 🍍💛
You may like also : Moist Pineapple Dream Cake : A Sweet Slice of Paradise
Conclusion – A Bite of Sunshine You’ll Never Forget
Pineapple Upside Sugar Cookies are more than just a dessert—they’re a mood. Each bite brings warmth, comfort, and a burst of tropical joy that makes life just a little sweeter.
With their golden caramelized bottoms, juicy pineapple bits, and buttery, melt-in-your-mouth texture, they’re proof that the simplest recipes can deliver the biggest rewards. Whether you’re baking for friends, family, or just yourself, these cookies will turn any day into a mini vacation.
So grab your mixing bowl, cue up your favorite island playlist, and get ready to bake up some sunshine. 🌴✨
FAQs
1. Can I use fresh pineapple instead of canned?
Yes! Just finely chop the fresh pineapple and make sure to drain it very well to avoid extra moisture. The flavor will be even brighter and fresher.
2. Why do I need to drain the pineapple so well?
Too much juice can make your dough sticky and cause the cookies to spread too much. Properly drained pineapple keeps them soft, chewy, and perfectly shaped.
3. Can I make these cookies ahead of time?
Absolutely! You can refrigerate the dough for up to 48 hours before baking or freeze baked cookies for up to 2 months. They’re great make-ahead treats.
4. How do I keep them from spreading too much?
Make sure the butter is softened, not melted, and chill the dough for at least 15 minutes before baking. A cooler dough holds its shape better in the oven.
5. What’s the best substitute for butter in this recipe?
You can use coconut oil or plant-based butter for a dairy-free option. It also enhances that tropical flavor beautifully!
