Oh my gosh, let me tell you about these Pineapple Upside Down Sugar Cookies! I was inspired to create this recipe during a summer barbecue when I first had that classic pineapple upside-down cake. The sweet, caramelized pineapple and the slight tang just blew my mind! I thought, why not turn that tropical delight into cookie form? So, I whipped up these delectable little treats that blend the rich flavor of brown sugar with juicy crushed pineapple and bright maraschino cherries. Trust me, every bite of these cookies is like a mini vacation to the beach! They’re chewy, soft, and just the right amount of sweet. If you’re ready to impress your friends and family with a cookie that’s bursting with flavor, this Pineapple Upside Down Sugar Cookies Recipe is the one to try!
Ingredients List
- 1 cup unsalted butter, softened
- 1 cup brown sugar, packed
- 1/2 cup granulated sugar
- 2 large eggs
- 2 teaspoons vanilla extract
- 3 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 cup crushed pineapple, drained
- 1/2 cup maraschino cherries, chopped
How to Prepare Pineapple Upside Down Sugar Cookies Recipe
Alright, let’s get those ovens preheated and dive into the magic of making these Pineapple Upside Down Sugar Cookies! First things first, preheat your oven to 350°F (175°C). This is super important because you want those cookies to bake evenly and turn out absolutely perfect.
Step-by-Step Instructions
- In a large mixing bowl, cream together the softened unsalted butter, packed brown sugar, and granulated sugar until it’s light and fluffy. This usually takes about 2-3 minutes, so don’t rush it!
- Next, add in the eggs, one at a time, along with that beautiful splash of vanilla extract. Mix until everything is combined and oh-so-smooth.
- In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. This step is crucial because it ensures your dry ingredients are well-mixed before adding them to the wet mixture.
- Gradually add the dry ingredients to the wet mixture, stirring just until everything is combined. Be careful not to overmix; we want those cookies to be tender!
- Now, it’s time for the fun part! Gently fold in the drained crushed pineapple and chopped maraschino cherries. Can you smell the tropical goodness already?
- Drop spoonfuls of the cookie dough onto a baking sheet lined with parchment paper, spacing them about 2 inches apart.
- Pop them in the preheated oven and bake for 12-15 minutes, or until the edges are golden brown. Keep an eye on them—they’ll be tempting to devour!
- Once baked, let the cookies cool on the baking sheet for about 5 minutes before transferring them to wire racks to cool completely. Patience is key here (I know, it’s hard!).
And voila! You’ve just created a batch of delightful Pineapple Upside Down Sugar Cookies that are sure to bring sunshine to any day!
Why You’ll Love This Recipe
- It’s a fun twist on the classic pineapple upside-down cake, bringing that tropical flavor into cookie form!
- Simple ingredients that you probably already have in your pantry make it easy to whip up anytime.
- These cookies are delightfully chewy with a burst of juicy pineapple and sweet cherries in every bite.
- They bake quickly, so you can satisfy your sweet tooth in just about 30 minutes.
- Perfect for sharing at parties or just enjoying as a special treat at home.
Tips for Success
To make your Pineapple Upside Down Sugar Cookies truly shine, here are my top tips! First off, make sure to drain the crushed pineapple really well. I can’t stress this enough—excess moisture can lead to soggy cookies, and nobody wants that! If you have time, chilling the cookie dough for about 30 minutes can make it easier to handle and help the flavors meld beautifully.
When scooping the dough onto your baking sheet, use a cookie scoop for uniformity. This ensures even baking and gives you those lovely, round cookies we all crave. Keep an eye on the baking time; every oven is a little different. You want those edges golden but the centers still soft. And remember, they’ll continue to set a bit while cooling on the baking sheet, so don’t overbake! Happy baking!
Nutritional Information

Now, let’s talk numbers! Each Pineapple Upside Down Sugar Cookie is a delightful treat, and here’s a rough estimate of what you can expect per cookie:
- Calories: 150
- Fat: 7g
- Protein: 2g
- Carbohydrates: 20g
Keep in mind, these values are estimates and can vary based on the specific brands and measurements you use. But hey, a little indulgence never hurt anyone, right? Enjoy these cookies without guilt—they’re a sweet little slice of happiness!
FAQ Section
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple can be used, but make sure to finely chop and drain it well, just like you would with canned pineapple. This will help keep your cookies from getting too soggy.
How do I store leftover cookies?
Store your Pineapple Upside Down Sugar Cookies in an airtight container at room temperature for up to 5 days. If you want to keep them longer, you can freeze them for up to 2 months. Just make sure to separate layers with parchment paper!
Can I make the dough ahead of time?
Yes! You can prepare the cookie dough ahead of time and refrigerate it for up to 2 days. Just let it sit at room temperature for a few minutes before scooping and baking. This can actually enhance the flavors!
What if I don’t have maraschino cherries?
No worries! If you don’t have maraschino cherries, you can substitute with dried cherries or even chopped nuts for a delicious twist. The tropical flavor of the pineapple will still shine through!
Why are my cookies spreading too much?
If your cookies are spreading too much, it might be due to the butter being too warm or not enough flour in the dough. Make sure to measure your flour correctly and chill the dough if needed for better shape!
Storage & Reheating Instructions
Storing your Pineapple Upside Down Sugar Cookies is super easy! Just pop them in an airtight container at room temperature, and they’ll stay fresh for up to 5 days. If you want to keep them longer, you can freeze them! Just layer each cookie with parchment paper and place them in a freezer-safe container or bag. They’ll be good for up to 2 months. When you’re ready to enjoy them again, simply let them thaw at room temperature. No need to reheat—these cookies are delicious served at room temperature or even slightly chilled from the fridge!
Variations
Want to shake things up with your Pineapple Upside Down Sugar Cookies? Here are some fun variations to try! For a tropical twist, swap out the crushed pineapple for mashed ripe bananas or even diced mango. You can also experiment with different flavorings—how about adding a touch of coconut extract for that beachy vibe? If you’re feeling adventurous, throw in some toasted coconut flakes or chopped macadamia nuts for added crunch. And for a citrusy kick, mix in some lime zest—it pairs beautifully with the pineapple. The possibilities are endless, so get creative and make these cookies your own!
Print
Pineapple Upside Down Sugar Cookies Recipe for Tropical Bliss
- Total Time: 30 minutes
- Yield: 24 cookies 1x
- Diet: Vegetarian
Description
Delicious cookies with a tropical twist from pineapple and brown sugar.
Ingredients
- 1 cup unsalted butter, softened
- 1 cup brown sugar, packed
- 1/2 cup granulated sugar
- 2 large eggs
- 2 teaspoons vanilla extract
- 3 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 cup crushed pineapple, drained
- 1/2 cup maraschino cherries, chopped
Instructions
- Preheat your oven to 350°F (175°C).
- Cream together butter, brown sugar, and granulated sugar.
- Add eggs and vanilla; mix well.
- In a separate bowl, combine flour, baking soda, and salt.
- Gradually add dry ingredients to the wet mixture.
- Fold in crushed pineapple and chopped cherries.
- Drop spoonfuls of dough onto a baking sheet.
- Bake for 12-15 minutes or until edges are golden.
- Let cool on the baking sheet for 5 minutes before transferring to wire racks.
Notes
- Ensure pineapple is well-drained to avoid soggy cookies.
- Chill dough for better handling.
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 150
- Sugar: 10g
- Sodium: 80mg
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 20g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 30mg
Keywords: Pineapple Upside Down Sugar Cookies Recipe
