There’s something magical about the aroma of warm cookies wafting through the house, especially when those cookies are Pineapple Upside-Down Cookies. Imagine biting into a soft, buttery treat topped with caramelized pineapple and cherries, bursting with flavor and nostalgia. The sweetness dances on your palate while the chewy texture makes every bite feel like a warm hug.
I first stumbled upon this delightful recipe during a family gathering when my cousin decided to experiment in the kitchen. Let me tell you, it was love at first bite! The perfect mix of tropical flavors and cookie goodness turned that ordinary day into a cherished memory. These cookies are not just for dessert; they’re perfect for any occasion, from summer picnics to cozy winter evenings.
Why You'll Love This Recipe
- These Pineapple Upside-Down Cookies are incredibly easy to prepare, making them a no-fuss dessert option
- With their vibrant colors and tropical flavors, they bring sunshine to any table
- Each cookie offers a delightful blend of buttery softness and caramelized sweetness that’s simply irresistible
- They’re versatile enough for any event or as an everyday treat you can whip up in no time!
I remember one time when I brought these cookies to a potluck, and people were practically fighting over the last crumb.

Essential Ingredients
Here’s what you’ll need to make this delicious dish:
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Unsalted Butter: Use room temperature butter for easy mixing and a rich flavor that brings out the best in your cookies.
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Granulated Sugar: This sweetener is essential for that perfect cookie balance; be sure to use fine sugar for even blending.
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Brown Sugar: Adds depth and moisture; light or dark works, but dark gives an extra caramel flavor.
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Pineapple Rings: Choose canned pineapple rings packed in juice for convenience; fresh pineapple can work if you’re feeling adventurous!
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Maraschino Cherries: These little gems add color and sweetness; feel free to use fresh cherries if they’re in season.
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All-Purpose Flour: Standard flour will do; measure carefully to keep your cookies from turning out too dense.
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Baking Powder: This helps your cookies rise perfectly; ensure it’s fresh for optimal results.
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Eggs: You’ll need one large egg to bind everything together nicely.
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Vanilla Extract: Pure vanilla extract enhances the overall flavor profile; skip imitation for the best taste.
The full ingredients list, including measurements, is provided in the recipe card directly below.
Let’s Make it together
Preheat Your Oven: Start by preheating your oven to 350°F (175°C). This ensures your cookies bake evenly and turn golden brown.
Prepare Your Baking Sheet: Line a baking sheet with parchment paper or spray it lightly with cooking spray. This prevents sticking and makes cleanup a breeze.
Create Your Topping Base: In a small bowl, mix brown sugar with melted butter until well combined. Spread this mixture evenly across the bottom of each cookie space on your baking sheet.
Add Pineapple and Cherries: Place one pineapple ring in each section of your prepared base and tuck a maraschino cherry in the center of each ring. This will give those cookies their signature upside-down charm!
Mix Your Cookie Dough: In another bowl, cream together butter, granulated sugar, brown sugar, egg, and vanilla extract until fluffy—about 3 minutes should do it! Then gently fold in flour mixed with baking powder until just combined.
Scoop That Dough!: Using a spoon or cookie scoop, place generous dollops of dough on top of each pineapple-cherry base. Make sure they’re spaced apart; these beauties will spread as they bake!
Bake Away!: Slide your baking sheet into the oven and bake for 12-15 minutes or until edges are golden brown and centers are set. Enjoy the heavenly aroma filling your kitchen!
Once baked to perfection, let them cool for about five minutes before flipping them onto a wire rack or serving platter. These Pineapple Upside-Down Cookies are sure to impress friends and family alike!
You Must Know
- Pineapple Upside-Down Cookies are not just delightful; they’re a tropical escape in every bite
- The warm, buttery flavor pairs perfectly with the sweet pineapple, making it a favorite for gatherings
- These cookies are easy to whip up and sure to impress your friends and family
Perfecting the Cooking Process
Start by preheating your oven while you prepare the cookie dough. This ensures even baking and a chewy texture. Bake until golden brown and let them cool before serving for the best flavor.

Add Your Touch
Feel free to experiment with different fruits like cherries or peaches instead of pineapple. You can also add nuts or coconut flakes for extra texture and flavor. Customize it to match your taste!
Storing & Reheating
Store your cookies in an airtight container at room temperature for up to a week. If you want to enjoy them warm later, pop them in the microwave for a few seconds before serving.
Chef's Helpful Tips
- To make the perfect Pineapple Upside-Down Cookies, ensure your butter is softened but not melted
- Also, use fresh pineapple for a burst of flavor, avoiding canned options whenever possible
- Finally, watch the baking time closely to prevent over-baking and maintain that delightful chewiness!
Creating these cookies brings back memories of family gatherings where everyone eagerly awaited dessert. Friends would always ask for seconds, and I happily obliged, filled with pride at my tropical masterpiece.
FAQ
Can I use canned pineapple for Pineapple Upside-Down Cookies?
Yes, but fresh pineapple offers a brighter flavor and better texture in cookies.
How do I prevent my cookies from spreading too much?
Chill the cookie dough for 30 minutes before baking to help them maintain their shape.
What’s the best way to serve Pineapple Upside-Down Cookies?
Serve them warm with a scoop of vanilla ice cream on top for an indulgent treat!
Pineapple Upside-Down Cookies
- Total Time: 30 minutes
- Yield: Approximately 16 cookies 1x
Description
Pineapple Upside-Down Cookies are a delightful twist on a classic dessert, combining the tropical flavors of caramelized pineapple and cherries with a soft, buttery cookie. These treats are not only easy to make but also add a splash of color and sweetness to any occasion, from summer picnics to cozy gatherings. Imagine the warm aroma filling your kitchen as you indulge in these nostalgic bites that promise to be a crowd-pleaser!
Ingredients
- 1/2 cup unsalted butter, room temperature
- 1/2 cup granulated sugar
- 1/2 cup brown sugar (light or dark)
- 1 cup all-purpose flour
- 1 tsp baking powder
- 1 large egg
- 1 tsp vanilla extract
- 8 canned pineapple rings, packed in juice
- 8 maraschino cherries
Instructions
- Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
- In a small bowl, mix together melted butter and brown sugar until well combined; spread this mixture on the bottom of each cookie space on the baking sheet.
- Place one pineapple ring and one maraschino cherry in each section.
- In another bowl, cream together butter, granulated sugar, brown sugar, egg, and vanilla extract until fluffy. Fold in flour mixed with baking powder until just combined.
- Scoop dough onto each prepared base and bake for 12-15 minutes or until golden brown.
- Allow cooling for five minutes before flipping onto a wire rack.
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: Tropical
Nutrition
- Serving Size: 1 cookie (40g)
- Calories: 150
- Sugar: 10g
- Sodium: 65mg
- Fat: 6g
- Saturated Fat: 4g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 24g
- Fiber: <1g
- Protein: 1g
- Cholesterol: 30mg
Keywords: - Substitute fresh pineapple for canned for an enhanced flavor experience. - Experiment with other fruits like peaches or cherries for creative variations. - Chill the dough for 30 minutes before baking to prevent spreading.



