Pineapple Upside Sugar Cookies Recipe
If you’re searching for a fun twist on a timeless favorite, Pineapple Upside Sugar Cookies might just steal your heart (and tastebuds). These cookies channel all the nostalgic flair of a classic pineapple upside-down cake, but in convenient, individual form. Imagine buttery sugar cookie dough hugging a jewel-red cherry and a crown of sweet, sunny pineapple—all caramelized beautifully into one delightful treat. The perfect balance of fruity tang and rich cookie comfort makes these a must-bake for the dessert lover in all of us.
Ingredients You’ll Need
You’ll be surprised at how these simple pantry and fridge staples combine to create a showstopping cookie. Every ingredient brings something special—whether texture, sweetness, or color—to this playful spin on a retro favorite.
- Unsalted butter (1 cup, softened): The foundation for that tender, melt-in-your-mouth cookie texture.
- Granulated sugar (1 cup): Brings sweetness and helps create that classic sugar cookie crumb.
- Large egg (1): Essential for binding everything together and adding richness.
- Vanilla extract (1 teaspoon): Adds cozy warmth and depth to balance out the fruity elements.
- All-purpose flour (2¼ cups): The sturdy backbone, keeping your cookies soft but not cakey.
- Baking soda (½ teaspoon): Ensures gentle lift and a perfectly light texture.
- Baking powder (½ teaspoon): Works alongside baking soda to make these cookies just the right amount of fluffy.
- Salt (¼ teaspoon): A pinch makes the sweetness pop and balances flavors.
- Crushed pineapple, well drained (½ cup): The star of the show, adding juicy bursts and classic pineapple upside-down flavor.
- Maraschino cherries, halved (12): For that iconic pop of color and a hit of candy-like fruitiness in every bite.
- Brown sugar (¼ cup): Adds caramel notes and helps create that signature sticky, upside-down effect.
- Melted butter (2 tablespoons): Mixes with brown sugar for the luscious pineapple base.
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), so it’s ready to work its magic. Line a large baking sheet with parchment paper for smooth, non-stick cleanup, and grease a 12-cup muffin tin lightly—this ensures your Pineapple Upside Sugar Cookies will release like a charm after baking.
Step 2: Create the Brown Sugar & Pineapple Base
In a small bowl, stir together the brown sugar and melted butter until you have a glossy, caramel-scented mixture. Spoon about half a teaspoon into each muffin cup, then nestle a cherry half, cut-side up, smack dab in the center. Surround each cherry with about a teaspoon of well-drained crushed pineapple, channeling those classic pineapple upside-down vibes.
Step 3: Mix the Cookie Dough
Cream together your softened butter and granulated sugar until the mix is light and super fluffy—this step gives your cookies their dreamy texture. Beat in the egg and vanilla. In a separate bowl, whisk the flour, baking soda, baking powder, and salt. Gradually mix the dry blend into your wet ingredients until a soft, supple dough forms.
Step 4: Assemble the Cookies
Scoop roughly 2 tablespoons of dough for each cookie (I like to roll them into balls and flatten slightly between my palms). Place each dough disc gently over the pineapple and brown sugar in the muffin tin, pressing lightly to help it reach the edges for that delicious “cookie crust.”
Step 5: Bake to Golden Perfection
Slide the muffin tin into your preheated oven and bake for 12 to 14 minutes, or until the edges take on a delicate golden hue. Let the cookies cool in the tin for 5 to 10 minutes—this small wait makes all the difference, letting the caramelized base set up just enough for a flawless flip.
Step 6: Invert and Cool
Once slightly cooled, carefully invert the muffin tin onto a wire rack so the pineapple-cherry side faces skyward. Gently lift each Pineapple Upside Sugar Cookie out (use a small offset spatula if needed). Let them finish cooling, or enjoy warm for maximum “just-baked” magic.
How to Serve Pineapple Upside Sugar Cookies
Garnishes
Add an extra sprinkle of powdered sugar for a snowy finish, or a tiny tuft of whipped cream if you’re feeling extra fancy. Some folks adore a drizzle of simple vanilla glaze while the cookies are still just a touch warm, highlighting those caramelized edges and glossy cherries.
Side Dishes
Pineapple Upside Sugar Cookies play beautifully alongside vanilla bean ice cream, a dollop of tangy Greek yogurt, or even a fresh fruit salad (for those who want to double down on the tropical feels). Pair them with coffee, black tea, or a fruity iced drink for a satisfying afternoon break.
Creative Ways to Present
Arrange the cookies on a tiered dessert stand for a retro-chic look, or tuck each one into a parchment cupcake liner for a sweet party bite. For holiday gatherings, swap out the maraschino cherries for candied cranberries or colored sprinkles to put your own spin on these Pineapple Upside Sugar Cookies.
Make Ahead and Storage
Storing Leftovers
These cookies are at their absolute best the day they’re baked, but you can store any extras in an airtight container at room temperature for up to two days. A layer of wax paper helps prevent sticking and keeps their caramelized tops intact.
Freezing
To freeze, let the Pineapple Upside Sugar Cookies cool completely. Place them in a single layer on a baking sheet to firm up, then transfer to a freezer-safe container, separating layers with parchment. They’ll keep well for up to two months—perfect for spontaneous cravings or make-ahead entertaining.
Reheating
A quick zap in the microwave (8–10 seconds) or a minute or two in a low oven revives their just-baked softness. If frozen, let them thaw at room temperature before reheating gently so the pineapple stays juicy but not mushy.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just chop it finely and make sure it’s well-drained—too much juice can lead to soggy cookies. Canned and fresh both bring their own flavor notes, so use what you love.
Do I have to use a muffin tin?
While a muffin tin gives each cookie its signature upside-down look and chewy caramelized base, you can experiment with mini tart pans or even a silicone muffin mold for easy release.
Can Pineapple Upside Sugar Cookies be made dairy-free?
Yes! Substitute your favorite plant-based butter for both the dough and the topping mixture. Be sure to use one meant for baking for the best results in taste and texture.
Why is draining the pineapple important?
Well-drained pineapple ensures your cookie bottoms stay firm and caramelized instead of soggy. Press the pineapple gently between layers of paper towel for the best texture.
What if I don’t have maraschino cherries?
No worries; you can use fresh or frozen cherries, pitted and halved, or substitute with a different jewel-toned fruit like raspberry or even dried cranberries for variety.
Pineapple Upside Sugar Cookies: Final Thoughts
I can’t wait for you to taste how perfectly nostalgic and downright fun these Pineapple Upside Sugar Cookies are! Whether you’re celebrating something special or just want to sweeten up a regular day, give this recipe a try and watch those sunny bites disappear—one happy cookie at a time.
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Pineapple Upside Sugar Cookies Recipe
- Total Time: 34 minutes
- Yield: 12 cookies 1x
- Diet: Vegetarian
Description
Indulge in the tropical sweetness of Pineapple Upside Sugar Cookies, a delightful twist on the classic pineapple upside-down cake. These soft, buttery cookies are topped with caramelized pineapple and a maraschino cherry for a burst of fruity flavor in every bite.
Ingredients
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
Topping:
- ½ cup crushed pineapple (well drained)
- 12 maraschino cherries (halved)
- ¼ cup brown sugar
- 2 tablespoons melted butter
Instructions
- Preheat oven and prepare tin: Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper. Grease a muffin tin and add brown sugar mixture and cherries.
- Prepare dough: Cream butter and sugar, add egg and vanilla. Combine dry ingredients and mix into a dough.
- Assemble cookies: Flatten dough balls, place over pineapple in tin, and bake.
- Cool and serve: Let cool, then invert onto a wire rack. Enjoy warm or at room temperature.
Notes
- Drain pineapple well to prevent sogginess.
- Best enjoyed fresh or store in an airtight container for up to 2 days.
- Prep Time: 20 minutes
- Cook Time: 14 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 210
- Sugar: 18g
- Sodium: 95mg
- Fat: 10g
- Saturated Fat: 6g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 28g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 35mg
