Pineapple Upside-Down Cookies Recipe
If you’re looking for a treat that combines nostalgia with sheer delight, you need to try Pineapple Upside-Down Cookies. These little gems capture all the fun and flavor of the classic cake—juicy pineapple, pops of cherry, buttery brown sugar caramel—in a perfectly portable, chewy cookie. Each bite bursts with a tropical, sunny sweetness that charms adults and kids alike. They’re easy enough for a weeknight baking session yet impressive enough for a special gathering. Trust me, one batch never seems to last long in my kitchen!
Ingredients You’ll Need
The magic of Pineapple Upside-Down Cookies lies in a handful of pantry staples and just a couple of fun, colorful touches. Each ingredient brings its own charm to the taste, texture, or irresistible look of the finished cookies.
- Crushed pineapple: Adds juicy flavor and a chewy, tropical texture to every bite; be sure to drain well for dough perfection.
- Unsalted butter: Makes the cookie base rich and tender, while giving structure to the buttery caramel layer.
- Brown sugar: Delivers that classic caramelized topping and keeps the cookies soft and flavorful.
- Large egg: Binds everything together and helps create that slightly cakey, soft crumb.
- Pure vanilla extract: Infuses the dough with warm, comforting aroma and depth.
- All-purpose flour: The backbone of the dough, giving the cookies their signature chew.
- Baking powder and baking soda: Team up to lift the cookies and keep them light.
- Salt: Just a touch to balance sweetness and brighten flavor.
- Maraschino cherries: For classic color and a juicy, sweet-tart bite right at the center.
- Granulated sugar: Sweetens the dough and ensures a delicately golden finish.
- Reserved pineapple juice: Enhances the tangy fruitiness and helps impart a little extra moisture.
How to Make Pineapple Upside-Down Cookies
Step 1: Prep the Oven and Pans
Begin by preheating your oven to 350°F (175°C). Line two baking sheets with parchment paper to guarantee easy cookie release and tidier cleanup. This ensures nothing sticks—especially important with sticky brown sugar involved!
Step 2: Mix the Brown Sugar Topping
In a small bowl, blend together the brown sugar and 2 tablespoons of softened butter. You’re looking for a crumbly, sandy mixture. This is your secret weapon for that gooey, caramel-like layer Pineapple Upside-Down Cookies are famous for. Set it aside while you make the dough.
Step 3: Cream Butter and Sugar
In a large bowl, beat the remaining softened butter with granulated sugar until it’s creamy, pale, and fluffy—about two to three minutes. Plenty of air whipped in here means your cookies will bake up soft and light.
Step 4: Add Egg, Vanilla, and Pineapple Juice
Beat in the egg, the vanilla extract, and the reserved pineapple juice until everything looks smooth and well-amalgamated. These fresh flavors lay the aromatic foundation beneath the tropical topping.
Step 5: Combine Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. This even distribution ensures each Pineapple Upside-Down Cookie rises perfectly and stays balanced, never overly salty or flat.
Step 6: Mix and Fold
Gradually stir the dry ingredients into the wet mixture, mixing just until combined. Don’t overwork the dough! Finally, gently fold in your well-drained crushed pineapple. If there’s extra juice, blot it out with a paper towel to avoid soggy dough.
Step 7: Assemble the Cookie Layers
Spoon about 1 teaspoon of the brown sugar-butter mixture into small mounds on your lined baking sheets, spaced at least 2 inches apart. Gently press a halved maraschino cherry into the center of each mound. These will form the signature candy–bright tops when you flip the cookies later.
Step 8: Top and Shape the Cookies
Scoop cookie dough over each brown sugar-cherry mound, using about a tablespoon of dough per cookie. Lightly flatten each mound with your fingers to help them bake evenly and to ensure full, flavorful coverage of the filling underneath.
Step 9: Bake and Flip
Bake for 10 to 12 minutes, or until the edges turn golden and the centers are just set. Let the cookies cool on the baking sheets for five minutes—this brief wait helps firm them up so the flip is easier!
Step 10: Unmold and Cool Completely
Carefully flip each cookie upside down while they’re still warm, revealing the glorious, sticky pineapple-cherry tops. Transfer to a wire rack and let cool completely. This final step gives your Pineapple Upside-Down Cookies their trademark look and lets them set to that perfect chewy, gooey consistency.
How to Serve Pineapple Upside-Down Cookies
Garnishes
For extra pizzazz, you can brush the tops of your cookies with a little reserved pineapple juice or a drizzle of simple glaze. A light dusting of powdered sugar or a sprinkle of toasted coconut flakes adds festive flair, making these cookies an even bigger showstopper at parties or potlucks.
Side Dishes
Pineapple Upside-Down Cookies are fun paired with vanilla ice cream, tangy Greek yogurt, or alongside a fresh fruit salad. They shine next to milky coffees or fruity teas—perfect for a sweet afternoon break, a fancy brunch, or a summery dessert platter.
Creative Ways to Present
Stack these cookies in pretty tins lined with parchment for a charming edible gift, or arrange them on a tiered serving tray for high-tea vibes. You can even slide a wooden skewer through each one and create a playful “cookie pop” display. However you serve them, the jewel-bright cherry centers steal the show!
Make Ahead and Storage
Storing Leftovers
Keep your leftover Pineapple Upside-Down Cookies in an airtight container at room temperature for up to three days. The brown sugar layer may get a touch stickier as time passes, but they’ll stay wonderfully soft and tempting.
Freezing
To freeze, place fully cooled cookies in a single layer or separated with parchment sheets in a freezer-safe container. They’ll keep their flavor and texture for up to a month—just don’t forget to thaw before serving.
Reheating
If your cookies seem a little firm after storage, pop them into a 300°F oven for 2-3 minutes or microwave for about 10 seconds. This gently revives their softness while reactivating the tropical aroma.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just chop it finely and drain well to prevent extra moisture in the dough. The flavor will be a bit brighter and less sweet, which some people really love in Pineapple Upside-Down Cookies.
Can I make these cookies gluten-free?
Yes, you can! Substitute a good-quality gluten-free all-purpose flour blend. Make sure it includes xanthan gum for the best chewy texture, and check that all your other ingredients are gluten-free.
Can I skip the maraschino cherries?
Of course; while the cherries are iconic, you could swap in dried cranberries for a tart bite or simply leave them out and let the pineapple shine solo.
Why do I need to drain the crushed pineapple?
Draining (and blotting, if very juicy) keeps your dough from turning out soggy. Too much liquid can make the cookies spread too much or bake up dense.
Can I make the dough ahead of time?
Yes! You can prepare the dough, cover, and refrigerate for up to 24 hours before assembling and baking. This can help the flavors develop for even yummier Pineapple Upside-Down Cookies.
Final Thoughts
Whether you’re reminiscing about classic cakes or searching for the ultimate cheerful cookie, Pineapple Upside-Down Cookies are guaranteed to brighten your day. I can’t wait to hear how you enjoy them—so gather your ingredients, bake up a batch, and treat yourself to this tropical twist on tradition!
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Pineapple Upside-Down Cookies Recipe
- Total Time: 32 minutes
- Yield: 24 cookies 1x
- Diet: Vegetarian
Description
Delight your taste buds with these Pineapple Upside-Down Cookies that bring a tropical twist to a classic dessert. Soft and chewy cookies topped with sweet pineapple and a cherry in the center, these treats are perfect for any occasion.
Ingredients
Dough:
- 1 cup crushed pineapple (drained)
- ½ cup unsalted butter (softened)
- ¾ cup brown sugar (packed)
- 1 large egg
- 1 teaspoon pure vanilla extract
- 1½ cups all-purpose flour
- 1 teaspoon baking powder
- ¼ teaspoon baking soda
- ¼ teaspoon salt
Topping:
- ½ cup maraschino cherries (halved)
- ½ cup granulated sugar
- 2 tablespoons reserved pineapple juice
Instructions
- Preheat the oven: Preheat the oven to 350°F (175°C) and line two baking sheets with parchment paper.
- Prepare the topping: In a small bowl, combine the brown sugar and 2 tablespoons softened butter until crumbly; set aside.
- Make the dough: In a large bowl, cream the remaining butter with granulated sugar until light and fluffy. Beat in the egg, vanilla extract, and reserved pineapple juice. In another bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, mixing until just combined. Fold in the drained crushed pineapple.
- Assemble the cookies: Place about 1 teaspoon of the brown sugar-butter mixture in small mounds on the baking sheets, spacing 2 inches apart. Press a halved maraschino cherry in the center of each mound. Scoop cookie dough over the sugar-cherry base, flattening slightly.
- Bake: Bake for 10–12 minutes, or until golden at the edges. Let cookies cool on the sheet for 5 minutes before flipping them over to reveal the pineapple-cherry top. Cool completely on a wire rack.
Notes
- For extra flavor, add ¼ teaspoon ground cinnamon to the brown sugar mixture.
- If the pineapple is very juicy, press it between paper towels before adding to the dough to prevent excess moisture.
- Store cookies in an airtight container for up to 3 days.
- Prep Time: 20 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 110
- Sugar: 11 g
- Sodium: 60 mg
- Fat: 4 g
- Saturated Fat: 2.5 g
- Unsaturated Fat: 1.5 g
- Trans Fat: 0 g
- Carbohydrates: 17 g
- Fiber: 0 g
- Protein: 1 g
- Cholesterol: 15 mg
