If you’re on the lookout for a delightful twist on classic cookies that brings a burst of tropical sunshine to your kitchen, the Pineapple Upside Down Sugar Cookies Recipe is exactly what you need. This charming recipe takes the nostalgic flavors of the beloved pineapple upside down cake and transforms them into perfectly soft, chewy sugar cookies topped with caramelized pineapple rings and bright maraschino cherries. The combination of buttery dough, caramelized brown sugar, and juicy pineapple creates a cookie experience that’s as visually stunning as it is delicious. Ready to impress your friends and family with a sweet treat that’s both familiar and refreshingly unique? Let’s dive in!
Ingredients You’ll Need
These ingredients come together in a wonderfully simple way, each playing an essential role from texture to tangy sweetness and that golden caramel finish. You’ll be amazed how such straightforward pantry staples can create a cookie that’s truly unforgettable.
- 1 cup butter, room temperature: Provides a rich, creamy base for the cookie dough helping achieve a tender crumb.
- 1 ½ cups granulated sugar: Sweetens the dough while aiding in creating a light texture.
- 2 eggs: Bind the ingredients together and add moisture for softness.
- 2 tsp vanilla extract: Enhances flavor with warm, aromatic notes.
- ½ cup sour cream: Adds a slight tang and keeps the cookies moist and tender.
- 3 cups all-purpose flour: The foundation for structure and chewiness.
- 1 tsp baking powder: Gives a gentle lift, ensuring the cookies aren’t dense.
- 1 tsp cornstarch: Contributes to a delicate, soft texture.
- ½ tsp salt: Balances sweetness and enhances all flavors.
- 13 canned pineapple slices: The star ingredient for that tropical flair, placed on top for eye-catching presentation.
- 13 maraschino cherries: Adds pops of vibrant color and sweet juiciness right in the center.
- ½ cup butter, melted: Used in the brown sugar topping to create that luscious caramel layer.
- 1 cup light brown sugar, packed: Mixes with the melted butter to form the signature sticky, sweet base underneath the pineapple.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Prepare the Cookie Dough
Start by creaming your room temperature butter and granulated sugar together until light and fluffy – this step infuses air into your dough for that perfect tenderness. Beat in the eggs one at a time, then stir in the vanilla extract and sour cream for that luscious step toward rich flavor. In a separate bowl, whisk together flour, baking powder, cornstarch, and salt. Gradually add your dry ingredients to the wet mixture, combining until just blended. The dough will be soft but manageable.
Step 2: Prepare the Topping
Mix the melted butter with the packed light brown sugar until fully combined. This luscious caramel mixture is key to the iconic upside down effect—it will soak into the cookie base and caramelize in the oven, giving you that gorgeous golden color and sweet depth.
Step 3: Arrange Pineapple and Cherry Toppings
In your prepared muffin or cookie pan, spoon about one tablespoon of the brown sugar mixture into the bottom of each cavity and spread it evenly. Carefully place a pineapple slice on top of the brown sugar, centering it beautifully. Nestle a maraschino cherry right in the middle of each pineapple ring. This attention to detail ensures your cookies will come out looking as fantastic as they taste.
Step 4: Fill with Dough and Bake
Drop generous scoops of cookie dough over the pineapple and brown sugar mixture, gently spreading or patting it downward to cover each piece. Bake at 350°F (175°C) for approximately 18-22 minutes, or until the cookie dough is just set and the edges are lightly golden. Keep an eye on them, as you want that perfect balance of soft center with a slight caramelized edge.
Step 5: Cool and Invert
Once baked, allow the cookies to cool in the pan for about 10 minutes so the caramel topping can set without sticking too much. Then carefully invert the pan onto a serving tray, revealing your stunning pineapple upside down decoration on each cookie. The warm hues and juicy toppings make these irresistible right from the start.
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
For an extra touch of elegance, sprinkle a tiny pinch of finely chopped toasted coconut around the edges after flipping. Freshly chopped mint leaves or a light dusting of powdered sugar can elevate the cookies visually and add a hint of fresh or sweet contrast to the caramel and pineapple flavors.
Side Dishes
These cookies pair brilliantly with a chilled glass of coconut milk or creamy vanilla ice cream to complement the tropical notes. For a warm beverage, think a spiced chai latte or creamy coffee—it’s a match made in flavor heaven.
Creative Ways to Present
Arrange these pineapple upside down sugar cookies on a vibrant tropical-themed platter adorned with fresh pineapple chunks and edible flowers for a party-ready display. Alternatively, serve them in a charming tin layered with parchment paper as a homemade gift that’s sure to delight anyone lucky enough to receive one.
Make Ahead and Storage
Storing Leftovers
Store your cookies in an airtight container at room temperature for up to 3 days. This will help maintain their soft texture and keep the pineapple moist and flavorful. If you prefer your cookies a little firmer, placing a slice of bread in the container can help modulate moisture.
Freezing
You can freeze baked cookies by wrapping them individually in plastic wrap, then placing them in a freezer-safe bag or container. Freeze for up to 2 months. When ready to enjoy, thaw at room temperature to preserve the texture and flavor beautifully.
Reheating
To enjoy these cookies with that fresh-from-the-oven warmth, gently reheat in a preheated oven at 300°F (150°C) for 5-7 minutes. This step revives that lovely caramel goodness and soft crumb that define the Pineapple Upside Down Sugar Cookies Recipe experience.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple can lend a brighter, fresher flavor. Just make sure to slice it evenly and pat dry to prevent excess moisture, which might affect the cookie texture.
What Pan Should I Use to Make These Cookies?
A muffin tin is ideal because it helps hold the pineapple slice and creates perfectly portioned cookies with that signature upside down look. If you don’t have one, you can use a regular cookie sheet but adjust toppings carefully.
Can I substitute maraschino cherries with something else?
Yes, you can swap them for glace cherries, dried cherries, or even small pieces of fresh strawberry for a similar pop of color and flavor.
Will these cookies be cakey or crunchy?
They strike a beautiful balance—soft and tender with a bit of chew, tempered by the slightly crisp caramelized brown sugar and pineapple topping.
Is it possible to make this recipe gluten-free?
Yes! Use a gluten-free all-purpose flour blend in place of regular flour. Just be sure the blend contains xanthan gum for best results in texture and structure.
Final Thoughts
Trust me when I say the Pineapple Upside Down Sugar Cookies Recipe is a total showstopper that brings joy and sunshine to any occasion. The combination of buttery cookie dough, caramelized brown sugar, and juicy pineapple with a cherry on top creates a flavor that’s both nostalgic and refreshingly new. Whether for a family dessert, a potluck, or gifts, these cookies will quickly become a favorite in your baking rotation. Give this recipe a try and watch as it becomes a sweet highlight in your kitchen adventures!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Total Time: 40 minutes
- Yield: 13 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
Delight in a tropical twist on classic sugar cookies with this Pineapple Upside Down Sugar Cookies recipe. Featuring soft, buttery cookies topped with caramelized pineapple slices and maraschino cherries, these treats combine the luscious flavors of a traditional pineapple upside-down cake with the simplicity of a cookie. Perfect for parties, afternoon snacks, or any occasion that calls for a sweet, fruity indulgence.
Ingredients
Cookie Dough
- 1 cup butter, room temperature
- 1 ½ cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- ½ tsp salt
Toppings
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Prepare Brown Sugar Mixture: In a bowl, combine the melted butter and light brown sugar until well blended. This mixture will create the caramelized base for the cookies, providing a rich, sweet flavor to complement the fruit toppings.
- Prepare Baking Pan: Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of your prepared baking pan—ideally a muffin or cookie cup pan. Spread it evenly to cover the bottom to ensure even caramelization during baking.
- Add Pineapple and Cherry: Place one pineapple slice on top of the brown sugar mixture in each cavity. Center a maraschino cherry in the middle of each pineapple slice for classic presentation and an added burst of sweetness.
- Make Cookie Dough: In a large bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Add eggs one at a time, beating well after each addition, then mix in the vanilla extract and sour cream until fully incorporated.
- Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet ingredients, mixing just until combined to form a soft dough.
- Fill Cookie Cups: Spoon the cookie dough evenly over the pineapple and cherry in each cavity, covering the fruit and the brown sugar mixture completely. This layering will bake into a delicious upside-down effect.
- Bake: Preheat your oven to 350°F (175°C). Bake the cookies for approximately 20-25 minutes or until the tops are golden brown and a toothpick inserted into the cookie part comes out clean.
- Cool and Invert: Allow the cookies to cool in the pan for about 10 minutes. Carefully invert the pan onto a cooling rack so the pineapple and cherries are on top, revealing the caramelized fruit topping.
- Serve: Let the cookies cool completely before serving to allow the topping to set, then enjoy these delightful pineapple upside down sugar cookies with tea or coffee.
Notes
- Use a non-stick or well-greased muffin pan for easy removal of the cookies after baking.
- If canned pineapple slices are not available, fresh pineapple slices can be used but should be slightly dried to avoid excess moisture.
- For a richer flavor, consider adding a pinch of cinnamon or nutmeg to the cookie dough.
- Store leftovers in an airtight container at room temperature for up to 3 days, or refrigerate for longer freshness.
- The cookie dough can be chilled for 30 minutes before baking to prevent spreading, if desired.
