Pineapple Upside-Down Sugar Cookies
If you’re looking for a delightful treat that combines the tropical sweetness of pineapple with the comforting flavor of sugar cookies, then you’ve come to the right place! These Pineapple Upside-Down Sugar Cookies are not only fun to make, but they also bring a smile to everyone who tries them. Imagine soft, chewy cookies topped with caramelized pineapple and a sweet cherry – it’s a match made in dessert heaven!
This recipe is perfect for busy weeknights or family gatherings. Whether you’re just craving something sweet or need a treat for your next get-together, these cookies will surely impress your friends and family alike. Let’s dive into this beloved recipe that’s sure to become a favorite in your home!
Why You’ll Love This Recipe
- Easy to Make: With simple steps and minimal prep time, you can whip these cookies up in no time!
- Family-Friendly Appeal: Kids and adults alike will love the delicious combination of flavors and textures.
- Make-Ahead Convenience: These cookies store well, so you can bake them ahead of time and enjoy them later.
- Impressive Presentation: The stunning topping makes for an eye-catching dessert that looks as good as it tastes.

Ingredients You’ll Need
Creating these Pineapple Upside-Down Sugar Cookies is a breeze with just a few simple and wholesome ingredients. You likely have many of these staples in your kitchen already! Here’s what you’ll need:
For the Topping:
- 1/2 cup unsalted butter, melted
- 1/2 cup brown sugar, packed
- 1 can (20 oz) pineapple slices, drained and cut into small pieces
- Maraschino cherries, halved
For the Sugar Cookies:
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- 2 1/2 cups all-purpose flour
- 1 tsp baking powder
- 1/4 tsp salt
Variations
One of the best things about this recipe is its flexibility! You can easily customize it to suit your taste or use what you have on hand. Here are some fun variations to consider:
- Add spices: Sprinkle in some cinnamon or nutmeg for an extra layer of warmth.
- Swap the fruit: Try using peaches or mangoes for a different fruity twist!
- Make it chocolatey: Add mini chocolate chips into the cookie dough for a rich contrast to the pineapple topping.
- Use whole wheat flour: Substitute half of the all-purpose flour with whole wheat flour for a healthier option.
How to Make Pineapple Upside-Down Sugar Cookies
Step 1: Prepare the Topping
First things first, let’s get that delicious topping ready! Preheat your oven to 350°F (175°C) and grease or line a muffin tin with parchment rounds. In a small bowl, mix together the melted butter and brown sugar until everything is well combined. Spoon about 1 tablespoon into each muffin cup, creating a sweet base that will caramelize beautifully during baking.
Step 2: Add the Pineapple and Cherries
Next up, let’s layer on that fabulous fruit! Place small pieces of pineapple on top of the brown sugar mixture in each muffin cup. Then, press half of a maraschino cherry right in the center of each one. This not only adds color but also complements the sweetness perfectly.
Step 3: Make the Sugar Cookie Dough
Now it’s time to whip up our cookie dough! In a large bowl, cream together the softened butter and granulated sugar until it becomes light and fluffy—this step helps incorporate air for soft cookies. Beat in one large egg and vanilla extract until everything is nicely combined.
Step 4: Combine Dry Ingredients
In another bowl, whisk together all-purpose flour, baking powder, and salt. Gradually add this dry mixture to your wet ingredients while mixing until a soft dough forms. This ensures even distribution of all ingredients throughout your cookies.
Step 5: Assemble the Cookies
Take about 1½ tablespoons of cookie dough and gently press it over the pineapple and cherry mixture in each muffin cup, flattening it slightly to cover everything evenly. This step is crucial because it allows all those wonderful toppings to meld into every bite!
Step 6: Bake Your Cookies
Pop those beauties into your preheated oven! Bake for about 12-15 minutes or until the edges are lightly golden brown. Your kitchen will smell amazing as they bake!
Step 7: Cool & Serve
Once baked, let them cool in the muffin tin for about five minutes before carefully flipping them onto a parchment-lined surface or cooling rack. Now they’re ready to be served warm or at room temperature – either way, enjoy every bit of that caramelized topping with your soft sugar cookie base!
Pro Tips for Making Pineapple Upside-Down Sugar Cookies
Creating the perfect Pineapple Upside-Down Sugar Cookies is easier than you might think! Here are some handy tips to elevate your baking experience.
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Use room temperature ingredients: This helps create a smooth and well-combined dough, ensuring that your cookies bake evenly and have the best texture.
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Don’t skip the chilling: If you find the dough too sticky, chilling it for 30 minutes can make it easier to handle. Chilled dough spreads less during baking, resulting in thicker cookies.
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Be generous with toppings: Make sure you don’t skimp on the caramelized pineapple and cherries. A good layer adds flavor and creates that beautiful presentation everyone will love!
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Check for doneness: Ovens can vary, so keep an eye on your cookies as they bake. The edges should be lightly golden while the center remains soft.
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Cool before serving: Letting your cookies cool slightly allows the topping to set, making them easier to serve without falling apart.
How to Serve Pineapple Upside-Down Sugar Cookies
These delightful cookies are not only a treat for your taste buds but also visually appealing! Here are some fun ideas on how to present them at your next gathering or simply enjoy them at home.
Garnishes
- Fresh mint leaves: A sprinkle of fresh mint adds a pop of color and a refreshing contrast to the sweetness of the cookies.
- Coconut flakes: Toasted coconut flakes can enhance the tropical vibes and provide a lovely crunch.
Side Dishes
- Vanilla Coconut Ice Cream: This creamy treat complements the warm cookies perfectly, offering a delightful contrast in temperature and flavor.
- Fruit Salad: A colorful mix of seasonal fruits can lighten up your dessert spread and add a refreshing bite.
- Whipped Coconut Cream: Light and fluffy coconut cream is an excellent non-dairy option that pairs beautifully with these sweet cookies.
- Iced Tea or Lemonade: A cold beverage like iced tea or lemonade provides a refreshing balance to the rich flavors of the cookies.
Serve these Pineapple Upside-Down Sugar Cookies with any of these garnishes or sides for an unforgettable dessert experience! Enjoy every bite!

Make Ahead and Storage
These Pineapple Upside-Down Sugar Cookies are not only delicious but also perfect for meal prep! You can easily make them ahead of time and store them for later enjoyment.
Storing Leftovers
- Store cookies in an airtight container at room temperature for up to 3 days.
- For longer freshness, keep them in the fridge for up to a week.
- If you notice the cookies becoming dry, consider adding a slice of bread to the container to help retain moisture.
Freezing
- To freeze, place the cooled cookies in a single layer on a baking sheet and freeze until solid.
- Once frozen, transfer them to a freezer-safe bag or container. They will keep well for up to 3 months.
- Label the bag with the date for easy reference.
Reheating
- To enjoy warm cookies, preheat your oven to 350°F (175°C).
- Place the cookies on a baking sheet and heat for 5-7 minutes until warmed through.
- Alternatively, you can microwave individual cookies for about 10-15 seconds.
FAQs
Here are some common questions you might have about making these delightful treats!
Can I use fresh pineapple for Pineapple Upside-Down Sugar Cookies?
Yes! Fresh pineapple works wonderfully as a substitute. Just ensure it’s cut into small pieces similar to canned pineapple.
How do I make Pineapple Upside-Down Sugar Cookies without eggs?
You can replace the egg with 1/4 cup unsweetened applesauce or 1/4 cup mashed banana. This will help bind the dough while keeping it moist.
Can I add nuts to my Pineapple Upside-Down Sugar Cookies?
Absolutely! Chopped nuts like walnuts or pecans can add a lovely crunch. Just fold them into the cookie dough before assembling.
How should I store Pineapple Upside-Down Sugar Cookies?
Store these cookies in an airtight container at room temperature for up to three days or refrigerate them for a week.
Final Thoughts
I hope you’re as excited as I am about making these Pineapple Upside-Down Sugar Cookies! They combine nostalgia with delightful flavors that everyone will love. Whether you’re preparing them for a special occasion or simply treating yourself, they’re sure to bring smiles all around. Enjoy baking, and remember to savor every bite!
Pineapple Upside-Down Sugar Cookies
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Total Time: 30 minutes
- Yield: Approximately 12 cookies 1x
- Category: Dessert
- Method: Baking
- Cuisine: Tropical
Description
Indulge in the delightful combination of tropical flavors with our Pineapple Upside-Down Sugar Cookies! These soft, chewy treats are topped with caramelized pineapple and a sweet cherry, creating a visually stunning and deliciously sweet dessert. Perfect for family gatherings or as a special treat for yourself, these cookies are easy to make and will surely impress everyone who tries them. With simple ingredients and straightforward steps, you can whip up these tropical delights in no time. Enjoy them warm or at room temperature for a delightful bite every time!
Ingredients
- 1/2 cup unsalted butter, melted
- 1/2 cup brown sugar, packed
- 1 can (20 oz) pineapple slices, drained and cut into small pieces
- Maraschino cherries, halved
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- 2 1/2 cups all-purpose flour
- 1 tsp baking powder
- 1/4 tsp salt
Instructions
- Preheat oven to 350°F (175°C) and grease or line a muffin tin.
- In a bowl, mix melted butter and brown sugar; spoon into muffin cups.
- Layer pineapple pieces on top, placing half a cherry in the center of each.
- In another bowl, cream softened butter and granulated sugar until fluffy. Add egg and vanilla.
- Whisk together flour, baking powder, and salt; gradually mix into wet ingredients until dough forms.
- Press cookie dough over the fruit mixture in each muffin cup.
- Bake for 12-15 minutes until lightly golden around the edges.
- Cool slightly before flipping onto a parchment-lined surface.
Nutrition
- Serving Size: 1 cookie (30g)
- Calories: 150
- Sugar: 10g
- Sodium: 100mg
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 21g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 20mg
