Pineapple Upside Down Sugar Cookies
Pineapple Upside Down Sugar Cookies That Delight Every Bite
Ah, the nostalgia of pineapple upside-down cake! It’s that delightful dessert that transports you back to summer picnics and family gatherings, isn’t it? Today, we’re taking that beloved classic and giving it a delicious twist in the form of Pineapple Upside Down Sugar Cookies. That’s right—these cookies will not only satisfy your sweet tooth but also impress everyone at your next cookie swap or family dessert night. If you’re a busy mom looking for a quick treat or a professional in need of a sweet escape, this recipe will become your go-to!
Why You’ll Love This Pineapple Upside Down Sugar Cookie Recipe
These Pineapple Upside Down Sugar Cookies are quick, easy, and oh-so-delicious! Imagine biting into a soft, chewy cookie crowned with caramelized pineapple and a cherry on top—pure bliss! The sweet, buttery flavors mingle perfectly with the hint of tang from the pineapple, creating a cookie that’s not just a dessert, but a celebration in every bite. and let’s be honest, who can resist the combination of sugar, fruity goodness, and delightful nostalgia?
Ingredients
Here’s what you’ll need to whip up these delightful cookies:
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 cup brown sugar, packed
- 2 large eggs
- 1 teaspoon vanilla extract
- 4 cups all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
- 1 cup crushed pineapple, drained
- Maraschino cherries for garnishing
Directions
Step 1: Preheat the Oven
First things first, preheat that oven to 350°F (175°C). The aroma of baking cookies is the best air freshener, isn’t it?
Step 2: Cream the Butters and Sugars
In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until the mix is smooth and fluffy. This should take about 3-5 minutes. Ready to unleash that sweet aroma?
Step 3: Add the Eggs and Vanilla
Next up, beat in the eggs one at a time, and then stir in that luscious vanilla extract. Trust me; this will take your cookie to heaven and back!
Step 4: Mix the Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add this dry mix to the butter-sugar mixture, mixing until just combined. Feel free to channel your inner chef and throw in some extra love!
Step 5: Fold in the Pineapple
Gently fold the crushed pineapple into the cookie dough. This is where the magic happens! Your cookie dough will now have a tropical twist, making it super unique (with a taste of childhood).
Step 6: Shape and Bake
Scoop tablespoon-sized balls of dough onto a lined baking sheet. Place a maraschino cherry right in the center of each cookie. Pro tip: If you want extra caramelization on your pineapple, you could also sprinkle a little brown sugar over each cookie before baking!
Bake those beauties for about 10-12 minutes or until the edges are golden brown.
Step 7: Cool and Enjoy
Once they’re out of the oven, let the cookies cool on a baking sheet for a few minutes before transferring them to a wire rack. And then, the moment you’ve been waiting for—enjoy every delightful bite!
Cooking Tips
- Chilling the Dough: If you have time, chill your cookie dough for about 30 minutes before baking. This can help the cookies hold their shape better.
- Variations: Feel free to try other fruits like peaches or cherries for a different flavor profile. Cook with creativity!
- Picky Eaters: If your kids are adamant about not liking pineapple, add some shredded coconut or finely chopped nuts to the cookie mix for a fun twist. They’ll never see the pineapple coming!
FAQs
Can I substitute the butter for margarine?
Sure! However, butter gives a richer flavor, so use margarine if that’s what you have on hand.
How can I store leftovers?
Place cookies in an airtight container and enjoy them within a week—if they last that long!
Can I freeze the cookie dough?
Absolutely! You can freeze the dough for up to three months. Just thaw when you’re ready to bake.
Now, are you ready to impress friends, family, or even yourself with these Pineapple Upside Down Sugar Cookies? This delightful recipe not only satisfies those sweet cravings but also brings a touch of nostalgia to the table. Bake these cookies, savor each bite, and watch as everyone comes back for seconds (or thirds)!
If you enjoyed this mouthwatering cookie creation, check out some of my other delightful desserts here. Because who can resist the allure of a great cookie recipe?
Meta Description
Pineapple Upside Down Sugar Cookies are the perfect recipe for busy days. Quick, easy, and delicious, these cookies will delight every bite.

Pineapple Upside Down Sugar Cookies
Ingredients
Cookie Base
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 cup brown sugar, packed
- 2 large eggs
- 1 teaspoon vanilla extract
- 4 cups all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
Topping
- 1 cup crushed pineapple, drained
- as needed maraschino cherries for garnishing
Instructions
Preparation
- Preheat the oven to 350°F (175°C).
- In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until smooth and fluffy (about 3-5 minutes).
- Beat in the eggs one at a time, then stir in the vanilla extract.
- In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add to the butter-sugar mixture until just combined.
- Gently fold in the crushed pineapple into the cookie dough.
Baking
- Scoop tablespoon-sized balls of dough onto a lined baking sheet.
- Place a maraschino cherry in the center of each cookie. Optionally, sprinkle a little brown sugar over each cookie before baking.
- Bake for about 10-12 minutes or until the edges are golden brown.
- Let cool on the baking sheet for a few minutes before transferring to a wire rack.




