If you’re looking for a playful twist on a classic that’ll win hearts at first bite, Pineapple Upside Sugar Cookies are absolutely the treat to make. Imagine buttery sugar cookies smuggling gooey caramelized pineapple and a burst of cherry, all golden and inviting. These little treasures are as delightful to look at as they are to devour, combining retro charm with pure, sunny sweetness. Whether you’re baking for a holiday platter, family gathering, or just to satisfy your own craving for nostalgia, you’ll find these cookies impossible to resist.
Ingredients You’ll Need
This recipe keeps it joyfully simple, using ingredients you probably already have in your kitchen. Each one plays a starring role, from building structure to infusing those iconic layers of flavor and irresistible color.
- Unsalted butter: Softened butter is the secret to melt-in-your-mouth texture—don’t rush this step!
- Granulated sugar: Brings the classic sweetness that makes sugar cookies so craveable.
- Large egg: Acts as a binder and gives your cookies that lovely, tender crumb.
- Vanilla extract: Adds warmth and rounds out the fruity notes with aromatic sweetness.
- All-purpose flour: Provides structure and helps the cookies hold up to the juicy filling.
- Baking soda: Lifts the dough so your cookies bake up light, not dense.
- Baking powder: Partners with baking soda to ensure perfect puffiness.
- Salt: Just a pinch accentuates all the sweet, fruity flavors.
- Crushed pineapple (well drained): The must-have topping—make sure you squeeze out excess juice for the perfect balance.
- Maraschino cherries (halved): Create that pop of color and classic “upside down” look.
- Brown sugar: Helps caramelize the bottom layer for that signature upside down magic.
- Melted butter: Blends with brown sugar and bathes the fruit for gorgeous caramelization.
How to Make Pineapple Upside Sugar Cookies
Step 1: Prep the Oven and Muffin Tin
Start by preheating your oven to 350°F (175°C)—no one likes waiting for the oven when excitement is building! Lightly grease a 12-cup muffin tin and line a large baking sheet with parchment paper, so your cookies release easily after baking and you capture all the caramel yumminess.
Step 2: Create the Upside Down Topping
In a small bowl, stir together brown sugar and melted butter until you have a glossy, sandy mixture. Spoon about half a teaspoon of this goodness into each muffin cup. Place a cherry half (cut side up) right in the center of every cup, then gently scatter about a teaspoon of well-drained crushed pineapple around each cherry. This fruity base sets the stage for the Pineapple Upside Sugar Cookies’ big reveal.
Step 3: Make the Sugar Cookie Dough
Cream the softened butter and granulated sugar together in a large bowl until it looks pale, light, and fluffy (think frosting clouds!). Beat in the egg and vanilla extract—you’ll see the mixture become delightfully creamy and fragrant. In another bowl, whisk together flour, baking soda, baking powder, and salt. Add these dry ingredients gradually to your wet mixture, mixing until a soft, scoopable dough forms. Don’t worry if it seems a bit sticky; that’s what makes these cookies so buttery!
Step 4: Assemble and Shape Your Cookies
Scoop about two tablespoons of dough and roll it into a ball for each cookie. Flatten each ball slightly into a disc between your hands, then lay it gently over the pineapple and cherry in every muffin cup. Press down very lightly—just enough to cover the fruit without squishing out the magic.
Step 5: Bake and Unmold
Bake for 12 to 14 minutes, or until the edges are turning a lovely light golden color. Let the cookies cool in the muffin tin for five to ten minutes (this allows the topping to set a bit), then run a small knife around the edges and carefully invert them onto a wire rack. Watching the Pineapple Upside Sugar Cookies release with their golden tops and little cherry centers will never get old!
How to Serve Pineapple Upside Sugar Cookies
Garnishes
For a finishing touch, dust your cookies lightly with powdered sugar, or drizzle with a simple vanilla glaze. A tiny mint leaf or an extra cherry on top makes them look extra charming and party-ready.
Side Dishes
Serve Pineapple Upside Sugar Cookies alongside fresh fruit salads, a small scoop of vanilla ice cream, or even with a crisp glass of sparkling lemonade. These accompaniments highlight the retro dessert’s sunny attitude.
Creative Ways to Present
Try arranging the cookies on a tiered cake stand for a showstopping brunch table, or package them individually in cellophane bags for adorable edible gifts. They’re also perfect for stacking in a playful “cookie tower” that’s sure to impress.
Pineapple Upside Sugar Cookies: Make Ahead and Storage
Storing Leftovers
Once completely cooled, store your cookies in an airtight container at room temperature. They’ll stay delicious and moist for up to 2 days—but trust me, they rarely last that long!
Freezing
If you want to make Pineapple Upside Sugar Cookies ahead of time, let the cookies cool fully, then layer them gently in a freezer-safe container with parchment paper between each layer. Freeze for up to one month for an instant taste of summer, any time.
Reheating
To revive that just-baked magic, pop thawed cookies on a baking sheet and warm them in a 300°F oven for 4–5 minutes. The fruit will glisten, and the edges will crisp up beautifully once again.
FAQs
Can I use fresh pineapple instead of canned crushed pineapple?
Absolutely! Just be sure to finely chop your fresh pineapple and pat it dry with paper towels. The key is to remove as much moisture as possible so you get that lovely caramelized base, not a soggy one.
Do I have to use a muffin tin?
The muffin tin helps keep all the juicy fruit and caramel neatly under each cookie for that iconic look, but you could use a ramekin or silicone muffin mold in a pinch for similar results.
Can I make Pineapple Upside Sugar Cookies gluten-free?
You sure can. Substitute a measure-for-measure gluten-free flour blend for the all-purpose flour, and keep an eye on texture; you may need a splash of milk if the dough is crumbly.
How do I prevent the cookies from sticking when unmolding?
Be generous when greasing your muffin tin, and let the cookies cool for at least 5 minutes after baking before inverting. Running a thin knife gently around the edge helps release them cleanly.
Can I double the recipe for a party?
Definitely. Simply use two muffin tins or bake in batches, and you’ll have plenty of Pineapple Upside Sugar Cookies for a crowd. Everyone loves the combination of buttery cookie, caramel, pineapple, and cherry in every bite!
Final Thoughts
If you love creative desserts and a little burst of nostalgia, don’t wait to bake a batch of Pineapple Upside Sugar Cookies. The sunny flavors, charming presentation, and pure joy in every bite make these cookies a guaranteed favorite. Gather your ingredients, invite some friends over, and let the delicious memories begin!
Print
Pineapple Upside Sugar Cookies Recipe
- Prep Time: 20 minutes
- Cook Time: 14 minutes
- Total Time: 34 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
Indulge in a delightful twist on traditional pineapple upside-down cake with these Pineapple Upside Sugar Cookies. These sweet treats feature a buttery cookie base topped with a pineapple ring, a maraschino cherry, and a brown sugar glaze.
Ingredients
For the Cookie Dough:
- 1 cup unsalted butter (softened)
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2¼ cups all-purpose flour
- ½ teaspoon baking soda
- ½ teaspoon baking powder
- ¼ teaspoon salt
For Topping:
- ½ cup crushed pineapple (well drained)
- 12 maraschino cherries (halved)
- ¼ cup brown sugar
- 2 tablespoons melted butter
Instructions
- Prepare the Topping: Preheat oven to 350°F (175°C). Grease a muffin tin and combine brown sugar with melted butter. Spoon mixture into 12 cups, add a cherry half and pineapple.
- Make the Cookie Dough: Cream butter and sugar, then mix in egg and vanilla. Combine dry ingredients separately and gradually add to wet mixture.
- Assemble and Bake: Form dough into balls, flatten, and place over toppings. Bake for 12–14 minutes until golden. Cool, then invert onto a rack.
Notes
- Thoroughly drain pineapple to prevent sogginess.
- Best served fresh but can be stored for up to 2 days in an airtight container.
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