Get ready to delight your taste buds with the irresistibly fun Pineapple Upside Down Sugar Cookies Recipe! Imagine all the retro charm of the classic pineapple upside down cake, packed into buttery, golden sugar cookies with bursts of tangy pineapple and ruby-red cherries. These cookies are a sunny, sweet treat that’s every bit as cheerful as they look, blending caramelized brown sugar with tropical fruit and a pillowy cookie base. Best of all? They’re a breeze to make—even if you’re not a seasoned baker. This is a perfect recipe for sharing, gifting, or brightening up any dessert table.
Ingredients You’ll Need
Every ingredient in this recipe is simple, but plays a crucial role—the right butter makes them indulgently melty, brown sugar adds crave-worthy caramel notes, and the classic fruit toppings really make these cookies shine both in color and flavor. Here’s what you’ll need (and why you won’t want to skip a thing):
- 1/2 cup unsalted butter, melted: This provides rich flavor and ensures your sugar cookies form that irresistible golden crust.
- 1/2 cup brown sugar, packed: For deep caramelization and a lovely, molasses-like sweetness.
- 12 maraschino cherries, halved: A classic, sweet-tart pop of color right in the center of every cookie—nostalgia at its finest!
- 1 can (20 ounces) pineapple tidbits, well drained: These juicy bursts add tropical flair and just the right amount of tang.
- 1 roll (16.5 ounces) refrigerated sugar cookie dough: The shortcut that brings everything together quickly, creating a soft and chewy base.
- 1/2 cup shredded sweetened coconut (optional): For extra texture and tropical flair—it toasts beautifully as a finishing touch.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Prep Your Muffin Tin
Start by preheating your oven to 350°F (175°C) and giving a 12-cup muffin tin a light greasing. This not only helps the cookies slip out easily after baking, but also ensures you get that gorgeous, caramelized edge. Even if your tin is nonstick, a little butter or spray goes a long way here.
Step 2: Create the Buttery Base
Pour the melted butter evenly into each muffin cup, ensuring that the bottom gets a generous coat. Following up, sprinkle in the brown sugar so it mixes with the butter—this duo will bubble up as the cookies bake, forming that signature sticky, golden goo.
Step 3: Add Pineapple and Cherries
Nestle a halved maraschino cherry, cut side down, into the center of each cup. Surround it with a few pieces of pineapple tidbits. The fruit will become glossy, sweet, and a bit jammy as it bakes, just like the classic cake (but in bite-sized form!).
Step 4: Top with Cookie Dough
Slice your refrigerated sugar cookie dough into 12 equally sized pieces for perfectly portioned cookies. Press each round gently over the fruit, flattening enough to seal everything underneath, but not so much that the dough seeps down the sides—you want a nice, even cookie “lid.”
Step 5: Bake to Golden Perfection
Pop the muffin tin into your preheated oven and bake for 18–20 minutes, until the cookies are lightly golden on top and set around the edges. Your kitchen will start to fill with the most delicious aroma—like a sunny bakery!
Step 6: Cool and Invert
Once out of the oven, give the cookies about 5 minutes to cool and settle in the pan. Then, gently run a knife around the edges of each cup to loosen any sticky bits. Carefully invert the muffin tin onto a baking sheet or your serving platter. The cookies should pop out, showing off their caramelized tops and jewel-like fruit centers.
Step 7: Add Finishing Touches
If you’re a fan of coconut, sprinkle each cookie with sweetened shredded coconut while they’re still warm. The coconut will gently toast, adding both texture and a fragrant hint of the tropics. Serve warm for maximum gooeyness and flavor!
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
A light sprinkle of extra toasted coconut or a dollop of whipped cream makes these cookies feel extra special. Even a drizzle of caramel sauce or a dusting of powdered sugar can turn a casual treat into a showstopper.
Side Dishes
Enjoy your Pineapple Upside Down Sugar Cookies Recipe with a scoop of vanilla ice cream, a fruit salad with more tropical flavors, or a chilled glass of pineapple juice. They’re also great alongside a cup of hot black tea or coffee, especially for an afternoon pick-me-up!
Creative Ways to Present
Arrange the cookies on a vintage cake stand or a sunny platter if you’re serving them at a gathering. For parties, wrap individual cookies in parchment and tie with twine for a sweet and shareable gift. Or, stack and skewer with extra pineapple chunks for a playful dessert kebab.
Make Ahead and Storage
Storing Leftovers
Store your leftover cookies in an airtight container at room temperature for up to two days. The cookie base will remain soft and the topping keeps its delicious stickiness, but for best flavor and texture, enjoy them as soon as possible.
Freezing
If you’d like to prepare ahead, these cookies freeze beautifully. Place completely cooled cookies in a single layer, separated by parchment paper, in a freezer-safe container. They’ll keep for up to three months—just thaw at room temperature when ready to eat.
Reheating
To recapture the just-baked magic, reheat the cookies in a 300°F (150°C) oven for 5 minutes, or microwave briefly (10–15 seconds) until warmed through. This will revive their gooey fruit topping and soft cookie center.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just chop the fresh pineapple into small, bite-sized tidbits and pat dry with paper towels to remove excess moisture so the cookie base stays crisp and not soggy.
What if I don’t have a muffin tin?
If you don’t own a muffin tin, you can use ramekins or even a mini cake pan. Just be sure to adjust baking time and keep an eye on the edges for doneness.
Can I make the Pineapple Upside Down Sugar Cookies Recipe gluten free?
For a gluten free version, swap in your favorite refrigerated gluten free sugar cookie dough. Everything else in the recipe is naturally gluten free, so everyone can enjoy!
Do I need to use coconut?
Not at all—the coconut is entirely optional! It does add a lovely chew and a hint of sweetness, but the cookies are delightful with or without it.
Why do I need to heavily drain the pineapple?
Excess moisture from the pineapple can make the cookies soggy. Draining ensures the caramelizes beautifully in the oven, keeping your Pineapple Upside Down Sugar Cookies Recipe perfectly gooey on top but soft and tender below.
Final Thoughts
It’s impossible not to fall in love with this Pineapple Upside Down Sugar Cookies Recipe—every batch is like bringing a little bit of sunshine into your kitchen. Whether you’re making a quick treat for family or impressing friends at your next gathering, I hope you give these cookies a try and share the joyful, tropical magic with everyone around you!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 20 minutes
- Total Time: 35 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
Indulge in the tropical flavors of these Pineapple Upside Down Sugar Cookies that are a delightful twist on the classic cake. These individual-sized treats feature a buttery brown sugar topping with pineapple and cherries, baked with sugar cookie dough for a sweet and fruity dessert.
Ingredients
For the cookies:
- 1/2 cup unsalted butter, melted
- 1/2 cup brown sugar, packed
- 12 maraschino cherries, halved
- 1 can (20 ounces) pineapple tidbits, well drained
- 1 roll (16.5 ounces) refrigerated sugar cookie dough
- 1/2 cup shredded sweetened coconut (optional)
Instructions
- Preheat and prepare: Preheat the oven to 350°F (175°C) and lightly grease a 12-cup muffin tin.
- Layer the base: Divide melted butter and brown sugar into the muffin cups. Add a cherry half in the center of each cup and arrange pineapple tidbits around it.
- Add the dough: Slice the cookie dough into 12 portions. Press a piece over the pineapple mixture in each cup, flattening slightly.
- Bake: Bake for 18–20 minutes until golden brown and set.
- Finish: Cool in the pan for 5 minutes, then invert onto a baking sheet. Optionally, sprinkle with shredded coconut before serving warm.
Notes
- For a more caramelized topping, bake the butter and sugar mixture for 2 minutes before adding fruit and dough.
- Best enjoyed fresh but can be stored for up to 2 days in an airtight container at room temperature.
Nutrition
- Serving Size: 1 cookie
- Calories: 210
- Sugar: 21 g
- Sodium: 150 mg
- Fat: 9 g
- Saturated Fat: 5 g
- Unsaturated Fat: 3 g
- Trans Fat: 0 g
- Carbohydrates: 32 g
- Fiber: 1 g
- Protein: 2 g
- Cholesterol: 15 mg
