Pineapple Upside Sugar Cookies Recipe
If you’ve ever had a classic pineapple upside-down cake and wished you could hold it in your hand for the perfect snack or party treat, these Pineapple Upside Sugar Cookies are ready to steal your heart. Each bite bursts with juicy pineapple, a pop of cherry, and buttery cookie all in one adorable package. They capture every nostalgic flavor from the beloved cake, but in a perfectly portioned, delightfully easy cookie – no forks required! This irresistible twist is destined to become a new favorite in your dessert lineup.
Ingredients You’ll Need
It’s amazing how a handful of everyday ingredients can transform into such a special treat. This is a celebration of classic flavors, each one working their magic to bring out vibrant colors and melt-in-your-mouth textures in Pineapple Upside Sugar Cookies.
- Unsalted butter (1 cup, softened): The rich, creamy base that keeps your cookies soft and tender.
- Granulated sugar (1 cup): The sweet backbone for our dough, giving it that irresistible cookie crunch.
- Large egg (1): Binds everything together while adding a bit of lift to the dough.
- Vanilla extract (1 teaspoon): Infuses warmth and depth, enhancing all the tropical flavors.
- All-purpose flour (2¼ cups): The structure that holds these chewy cookies just right.
- Baking soda (½ teaspoon): Lends a gentle rise, so every cookie is airy – never dense.
- Baking powder (½ teaspoon): Partners with baking soda for just the right amount of lift.
- Salt (¼ teaspoon): Pulls the sweetness into focus and balances everything out.
- Crushed pineapple (½ cup, well drained): The star fruit, responsible for that punchy, juicy flavor in every bite.
- Maraschino cherries (12, halved): Classic and bright – these sit atop each cookie for an eye-catching and nostalgic touch.
- Brown sugar (¼ cup): Creates a caramelized layer under the fruit, mimicking the upside-down cake vibe.
- Melted butter (2 tablespoons): Combines with brown sugar to make the gooey foundation, just like in the original dessert.
How to Make Pineapple Upside Sugar Cookies
Step 1: Prep Your Baking Pan
Start by preheating your oven to 350°F (175°C). Line a big baking sheet with parchment for easy clean-up later, but focus on your 12-cup muffin tin – give each cup a light coating of nonstick spray so nothing sticks. In a small bowl, stir together the brown sugar and melted butter. Spoon about ½ teaspoon of this sweet, buttery mix into the bottom of each muffin cup to create that signature caramelized base.
Step 2: Arrange Fruit in Each Cup
Take your maraschino cherry halves and place one in the center of every muffin cup, cut side facing up for maximum color. Around the cherry, gently nestle 1 teaspoon of well-drained crushed pineapple. This is your mini “upside down” layer – bright, cheerful, and perfectly juicy.
Step 3: Make the Cookie Dough
In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. This usually takes about 2-3 minutes of mixing and makes all the difference for tender cookies. Beat in the egg and vanilla until well combined. In a separate bowl, whisk the flour, baking soda, baking powder, and salt until combined, then slowly add your dry mixture into the wet mixture. Stir just until a soft dough comes together – don’t overmix!
Step 4: Shape and Assemble Cookies
Now, scoop about 2 tablespoons of dough and roll it into a ball for each cookie. Flatten each ball just a bit in your hands. Place the dough disks gently on top of the fruit-filled muffin cups, pressing lightly to cover the pineapple and cherry. This will bake into a beautiful “crust” with gooey fruit hiding underneath.
Step 5: Bake and Reveal
Slide the muffin tin into your preheated oven and bake for 12 to 14 minutes, just until the cookie edges are lightly golden. Let the cookies cool in the tin for 5 to 10 minutes so the fruit and caramel have time to set. Then, comes the fun part: run a knife around the edges and carefully invert each cookie onto a wire rack (“upside-down” style, of course) to reveal glossy fruit topping. Serve warm for melty, juicy magic – or let them cool for picnic-perfect treats.
How to Serve Pineapple Upside Sugar Cookies
Pineapple Upside Sugar Cookies Garnishes
A little garnish takes these cookies to the next level. Try a light dusting of powdered sugar, shredded coconut for a tropical crowd-pleaser, or even a tiny sprig of mint for a fancy touch. Each garnish enhances the fruity note and makes the cookies as fun to look at as they are to eat.
Side Dishes
If you’re serving Pineapple Upside Sugar Cookies at a gathering, consider a platter of fresh tropical fruit or a scoop of vanilla ice cream on the side. The cookies pair beautifully with brisk iced tea, subtly sweetened coffee, or even a pineapple-infused punch for a summer afternoon treat.
Creative Ways to Present
These cookies make a statement on a tiered dessert stand or stacked in pretty cupcake liners for grab-and-go style. For parties, consider packaging each cookie in small cellophane bags tied with ribbon for a take-home favor that delights both eyes and taste buds.
Make Ahead and Storage
Storing Leftovers
Cool your Pineapple Upside Sugar Cookies completely before stashing them in an airtight container. They’ll stay soft and lovely at room temperature for up to 2 days – perfect for a bake-ahead treat to share or savor on your own.
Freezing
If you’d like to make a batch ahead of time, these cookies freeze surprisingly well. Arrange cooled cookies in a single layer or with parchment between layers in a freezer-safe container. They’ll keep their flavor and texture for up to 1 month.
Reheating
To bring back that “just baked” magic, pop a thawed cookie in a 300°F oven for about 5 minutes, or microwave for 10-15 seconds. The sugars will soften, the fruit will glisten, and the cookie will be as irresistible as day one.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just make sure to chop it finely and drain it really well so your cookies don’t turn out soggy. Fresh pineapple brings an even brighter flavor to Pineapple Upside Sugar Cookies.
What if I don’t have a muffin tin?
You can mound the fruit and brown sugar mixture on a parchment-lined baking sheet, then top each with a cookie dough round. They’ll be a bit more rustic (and possibly spread a little more), but the flavors will still hit all the right notes.
Can I make these gluten-free?
Yes! Replace the all-purpose flour with your favorite 1-to-1 gluten free flour blend. Check cookies for doneness at the lower end of the baking time, as gluten-free dough tends to bake faster.
How do I keep the cookies from sticking when I invert them?
Be sure to thoroughly grease the muffin tin and let the cookies cool for at least 5 minutes before inverting. Running a small knife or offset spatula around the edges will also help release them cleanly.
Can I double the recipe for a crowd?
Definitely! Double all ingredients and use two muffin tins, rotating them halfway through baking for even results. Pineapple Upside Sugar Cookies are a great choice for sharing at big gatherings or festive events.
Final Thoughts
Whether you’re a nostalgic upside-down cake fan or just craving a bright, happy cookie, Pineapple Upside Sugar Cookies promise to bring sunshine to your kitchen. Each one is a perfect pocket of buttery dough, juicy pineapple, and cheery cherry – so go on, bake a batch, and watch them disappear! I can’t wait for you to experience this delightful fusion of comfort and fun in cookie form.
Print
Pineapple Upside Sugar Cookies Recipe
- Total Time: 34 minutes
- Yield: 12 cookies 1x
- Diet: Vegetarian
Description
Indulge in the tropical flavors of these Pineapple Upside Sugar Cookies, a delightful twist on the classic pineapple upside-down cake. These sweet treats feature a buttery cookie base topped with gooey pineapple and a cherry for a burst of color and flavor.
Ingredients
Cookies:
- 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.
- Make cookie dough: Cream butter and sugar, then add egg and vanilla. Combine dry ingredients and mix into a soft dough.
- Assemble cookies: Form dough balls, flatten and place over pineapple in muffin tin.
- Bake: Bake for 12–14 minutes until golden.
- Cool and serve: Let cool in tin, then invert onto a rack. Enjoy warm or at room temperature.
Notes
- Thoroughly drain pineapple to prevent sogginess.
- Best enjoyed fresh, 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
