Pineapple Upside-Down Cookies are like a tropical vacation for your taste buds, transporting you straight to a sunny beach with every bite. Imagine the sweet aroma of caramelized pineapple mingling with buttery cookie dough, creating a delightful treat that’s both chewy and crisp. pumpkin pie cupcakes The moment you take a bite, the flavors burst open like confetti at a party, leaving you craving more.
I remember the first time I made these cookies; my friends were skeptical at first. But when they took their first bites, their faces lit up as if they had just discovered buried treasure. Perfect for summer barbecues or cozy winter evenings, these cookies are bound to become a family favorite, enticing everyone with their unique flavor combination. Get ready for an unforgettable flavor experience!
Why You'll Love This Recipe
- Pineapple Upside-Down Cookies offer a quick and easy dessert option that pleases every palate
- They combine tropical flavors with classic cookie appeal for a delightful twist
- Visually stunning with vibrant colors, they are perfect for special occasions or casual snacking
- These cookies are versatile enough to be customized with your favorite fruits or nuts
I still chuckle when I think about how my grandmother tried to replicate this recipe after tasting it. cinnamon roll cake recipe Let’s just say that her version turned out quite differently—bless her heart!

Essential Ingredients
Here’s what you’ll need to make this delicious dish:
- Unsalted Butter: A must for that rich and creamy texture; always use room temperature butter for easy mixing.
- Brown Sugar: Opt for dark brown sugar for deeper caramel flavor; it adds that signature sweetness.
- Canned Pineapple Rings: Choose pineapple in juice instead of syrup for a fresher taste; it keeps the cookies lighter.
- All-Purpose Flour: Standard flour works best; sift it before measuring for light and fluffy cookies.
- Baking Powder: Essential for fluffiness; ensure it’s fresh to achieve maximum rise.
- Eggs: Use large eggs at room temperature; they help create an airy texture in your cookies.
- Vanilla Extract: Pure vanilla extract enhances the overall flavor profile; avoid imitation extracts if possible.
- Salt: Just a pinch balances the sweetness and enhances all flavors beautifully.
The full ingredients list, including measurements, is provided in the recipe card directly below. pumpkin hummus recipe.
Let’s Make it together
Preheat Your Oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking. For more inspiration, check out this Baked Potatoes in the Oven recipe.
Create the Pineapple Base: In a small saucepan over medium heat, melt one tablespoon of butter and add brown sugar until bubbling. Arrange pineapple rings on top as you daydream about sunny beaches.
Mix Your Cookie Dough: In a large bowl, cream together room temperature butter and brown sugar until fluffy. Add eggs one at a time, mixing well after each addition while trying not to eat all the dough.
Add Dry Ingredients: Gradually mix in flour, baking powder, and salt until combined. The dough should be thick but manageable—like trying to pull off those skinny jeans after Thanksgiving dinner!
Scoop and Bake: Using a cookie scoop or spoon, drop heaping tablespoons of dough onto prepared baking sheets over each pineapple ring. Bake for 12-15 minutes until edges turn golden brown and your kitchen smells heavenly.
Cool and Serve!: Allow cookies to cool on the baking sheet for 5 minutes before transferring them to wire racks. Try not to eat them all at once—they’re even better when shared!
You Must Know
- Pineapple Upside-Down Cookies are a delightful twist on the classic dessert
- These cookies offer a burst of tropical flavor and a chewy texture that will make your taste buds dance
- Perfect for parties or just because, they guarantee smiles all around
Perfecting the Cooking Process
Start by preheating your oven and preparing your cookie sheets. Mix your batter while the oven warms up for perfectly baked cookies. baked apples with cinnamon.

Add Your Touch
Feel free to experiment with different fruits like cherries or peaches for a unique spin on these cookies. You can also add nuts for crunch!
Storing & Reheating
Store cookies in an airtight container at room temperature. For reheating, pop them in the microwave for 10-15 seconds to restore softness.
Chef's Helpful Tips
- To achieve the perfect cookie texture, use room temperature butter for better creaming
- Avoid over mixing once you add the flour to keep them soft
- Always measure flour correctly—spoon it into the cup and level it off for accuracy
I remember baking these Pineapple Upside-Down Cookies for my best friend’s birthday party, and they vanished faster than I could say “yum.” Everyone raved about them! For more inspiration, check out this Chocolate Souffle recipe .
FAQ
Can I use fresh pineapple instead of canned?
Absolutely! Just make sure to finely chop it to avoid sogginess.
How do I prevent cookies from spreading too much?
Chill the dough before baking to help maintain shape in the oven.
What can I substitute if I don’t have brown sugar?
You can mix white sugar with a little molasses as a quick substitute.
Pineapple Upside-Down Cookies
- Total Time: 30 minutes
- Yield: Approximately 12 cookies 1x
Description
Pineapple Upside-Down Cookies are a delightful fusion of tropical flavors and classic cookie goodness. Each bite delivers the sweetness of caramelized pineapple paired with buttery, chewy cookie dough, creating an unforgettable treat that will transport your taste buds to a sunny paradise. Perfect for any occasion, these cookies are sure to impress family and friends alike!
Ingredients
- 1/2 cup unsalted butter (room temperature)
- 1 cup dark brown sugar
- 1 can (8 oz) pineapple rings in juice, drained
- 1 ½ cups all-purpose flour (sifted)
- 1 tsp baking powder
- 2 large eggs (room temperature)
- 1 tsp pure vanilla extract
- 1/4 tsp salt
Instructions
- Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
- In a small saucepan, melt 1 tablespoon of butter and stir in brown sugar until bubbling. Arrange the pineapple rings on top.
- In a mixing bowl, cream together the remaining butter and brown sugar until fluffy. Add eggs one at a time, mixing well after each addition.
- Gradually mix in flour, baking powder, and salt until the dough is thick but manageable.
- Drop heaping tablespoons of dough onto the prepared baking sheet over each pineapple ring.
- Bake for 12-15 minutes or until golden brown. Let cool on the baking sheet for 5 minutes before transferring to wire racks.
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: Tropical
Nutrition
- Serving Size: 1 cookie (40g)
- Calories: 150
- Sugar: 11g
- Sodium: 80mg
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 21g
- Fiber: <1g
- Protein: 1g
- Cholesterol: 30mg







