Oh my goodness, let me tell you about these Upside Down Pineapple Cookies! They’re like a tropical vacation for your taste buds! The moment you bite into one, you’re hit with that sweet, juicy pineapple flavor, perfectly balanced with the buttery cookie base. I can still remember the first time I made these for a family gathering. Everyone was diving in, and the laughter and chatter filled the kitchen. My cousin even dubbed them “tropical sunshine on a plate!” Trust me, they’re not just cookies; they’re a warm hug from summer, regardless of the season. So, if you’re looking to bring a little sunshine into your day, these cookies are just the ticket! Let’s dive into how to make these delightful treats!

Ingredients
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon salt
- 1 cup crushed pineapple, drained
- 1/2 cup brown sugar
- 1/4 cup maraschino cherries, halved
How to Make Upside Down Pineapple Cookies
Preheat and Prepare
First things first, let’s get that oven warmed up! Preheat it to 350°F (175°C). While that’s heating, grab your favorite baking dish and give it a good greasing. Trust me, this step is super important – you don’t want your delicious cookies sticking to the bottom! Once greased, set it aside and let’s move on to the fun part.
Make the Cookie Batter
In a large mixing bowl, let’s cream together the softened butter and granulated sugar until it’s nice and fluffy – this usually takes about 2-3 minutes. It’s such a satisfying step! Next, crack in those two large eggs and add the vanilla extract. Mix everything until it’s well combined; you want it to look smooth and creamy. Now, in another bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add this dry mix to the wet ingredients, stirring just until combined. Don’t overmix! Finally, fold in the crushed pineapple gently. This is where the tropical magic starts!
Assemble the Cookies
Now it’s time to layer the goodness! Sprinkle the brown sugar evenly across the bottom of your greased baking dish. This creates a lovely caramel layer. Next, arrange the halved maraschino cherries on top of that brown sugar – they’ll add a beautiful pop of color and flavor. Once that’s done, pour your cookie batter over the pineapple and cherries, spreading it out evenly. It’s okay if some of the cherries peek through; it just adds to the charm!
Bake and Cool
Pop your baking dish into the preheated oven and let it bake for about 25-30 minutes. You’ll know they’re done when the top is golden brown and a toothpick inserted into the center comes out clean. Once they’re baked to perfection, remove them from the oven and let them cool for a few minutes in the dish. This is key! After they’ve cooled a bit, carefully flip them upside down onto a serving plate. Now, get ready for the ooohs and aaahs as you unveil this delightful tropical treat!
Why You’ll Love This Recipe
- Unique tropical flavor: These cookies are like a slice of paradise with every bite! The combination of pineapple and cherries brings an irresistible sweetness that’s just so refreshing.
- Easy to make: Don’t worry if you’re not a baking pro! The steps are super simple, and you’ll be amazed at how quickly these come together.
- Great for gatherings: Whether it’s a family reunion or a cozy get-together with friends, these cookies are sure to impress and spark conversations around the table.
- Perfect dessert for any occasion: From summer barbecues to holiday feasts, these cookies fit right in, adding a tropical twist that everyone will love!
Tips for Success
Alright, let’s make sure your Upside Down Pineapple Cookies turn out absolutely perfect! Here are my top tips that I’ve picked up along the way:
- Use room temperature ingredients: Make sure your butter and eggs are at room temperature before starting. This helps them blend better, creating a smoother batter. Trust me, it makes a difference!
- Drain the pineapple well: If your crushed pineapple is too watery, it can make the cookies soggy. After draining, press it gently with a paper towel to remove any excess juice.
- Don’t overmix the batter: Once you combine the wet and dry ingredients, mix until just combined. Overmixing can lead to tough cookies. We want them tender and delightful!
- Keep an eye on the baking time: Ovens can vary, so start checking for doneness a minute or two early. A golden top and clean toothpick are your best signs!
- Let them cool properly: Cooling them in the dish for a few minutes before flipping helps them hold their shape, avoiding any messy disasters. Patience is key!
By following these tips, you’ll be well on your way to baking up some tropical magic that everyone will adore! Happy baking!
Nutritional Information
Just a quick note before we dive into the numbers: nutritional values can vary based on the specific brands and ingredients you use, so these are just estimates. That being said, here’s a breakdown of what you can expect for each cookie:
- Calories: 150
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Cholesterol: 30mg
- Sodium: 100mg
- Carbohydrates: 20g
- Fiber: 1g
- Sugar: 10g
- Protein: 2g
So there you have it! These cookies are a delightful treat that brings a burst of tropical flavor without being overly heavy. Enjoy them as a sweet indulgence, and remember, moderation is key to keeping that balance! Happy baking and snacking!
FAQ Section
Can I use fresh pineapple instead of canned?
Absolutely! Using fresh pineapple can elevate your Upside Down Pineapple Cookies to a whole new level. Fresh pineapple has a more intense flavor and firmer texture, which can make your cookies even more delicious. Just make sure to chop it finely and drain it well to avoid excess moisture. You’ll be amazed at how vibrant and zesty your cookies taste with that fresh fruit goodness!
How do I store the cookies?
To keep your cookies fresh and tasty, store them in an airtight container at room temperature. They should stay delicious for about 3-5 days. If you live in a particularly humid area, consider placing a piece of parchment paper between the cookies to prevent them from sticking together. Trust me, you want to savor every last crumb!
Can I freeze these cookies?
Yes, you can definitely freeze your Upside Down Pineapple Cookies! Just let them cool completely, then wrap each cookie individually in plastic wrap and place them in a freezer-safe bag. They’ll keep well for up to 2 months. When you’re ready to enjoy them, simply thaw in the fridge overnight and then enjoy them at room temperature or pop them in the microwave for a few seconds for a warm treat. It’s like having a little tropical vacation waiting for you in the freezer!
Serving Suggestions
These Upside Down Pineapple Cookies are delightful on their own, but why not elevate your tropical experience with some fun pairings? Here are a few ideas to enhance your cookie enjoyment:
- Whipped Cream: A dollop of fresh whipped cream adds a light and airy touch, perfectly complementing the sweetness of the cookies.
- Ice Cream: Serve warm cookies with a scoop of vanilla or coconut ice cream for an indulgent treat that’s simply irresistible.
- Tropical Fruit Salad: Pair these cookies with a vibrant fruit salad featuring mango, kiwi, and berries for a refreshing contrast.
- Coconut Flakes: Sprinkle some toasted coconut flakes on top for added texture and that extra tropical vibe.
- Hot Beverage: Enjoy them with a cup of coffee, tea, or even a fruity iced drink to bring out the tropical flavors even more!
These simple additions will make your cookie experience even more delightful, so feel free to mix and match to find your perfect pairing!
Print
Upside Down Pineapple Cookies: 5 Steps to Tropical Bliss
- Prep Time: 15 minutes
- Cook Time: 30 minutes
- Total Time: 45 minutes
- Yield: 24 cookies 1x
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
Delicious upside down pineapple cookies with a sweet and tropical flavor.
Ingredients
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon salt
- 1 cup crushed pineapple, drained
- 1/2 cup brown sugar
- 1/4 cup maraschino cherries, halved
Instructions
- Preheat your oven to 350°F (175°C).
- In a bowl, cream together the butter and granulated sugar.
- Add eggs and vanilla; mix well.
- In another bowl, combine flour, baking powder, and salt.
- Gradually add dry ingredients to the wet mixture.
- Fold in crushed pineapple.
- In a greased baking dish, sprinkle brown sugar on the bottom.
- Arrange maraschino cherries on top of the brown sugar.
- Pour the cookie batter over the pineapple and cherries.
- Bake for 25-30 minutes or until golden brown.
- Let cool before flipping upside down to serve.
Notes
- Use fresh pineapple for a more intense flavor.
- Store cookies in an airtight container.
- Best served warm or at room temperature.
Nutrition
- Serving Size: 1 cookie
- Calories: 150
- Sugar: 10g
- Sodium: 100mg
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 20g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 30mg
Keywords: Upside Down Pineapple Cookies, Pineapple Cookies, Tropical Cookies