Delight in the world of Pineapple Upside Down Sugar Cookies, a scrumptious twist on the classic dessert. These cookies combine the delightful flavors of caramelized pineapple with soft, buttery sugar cookies, making them perfect for any occasion—from casual gatherings to festive celebrations. With their vibrant appearance and unique taste, these treats are sure to impress family and friends alike.
Why You’ll Love This Recipe
- Easy to Make: With just a few simple steps, you can whip up these cookies in no time, even if you’re a beginner.
- Unique Flavor: The combination of sweet sugar cookie dough and tangy pineapple creates a delicious flavor explosion.
- Versatile Treat: Whether for parties, holidays, or an afternoon snack, these cookies fit every occasion.
- Visually Appealing: The golden-brown pineapple rings on top make these cookies as beautiful as they are tasty.
- Kid-Friendly Fun: Kids will love helping to arrange the pineapple on the dough, making it a fun family activity.
Tools and Preparation
To create your Pineapple Upside Down Sugar Cookies, having the right tools makes all the difference. Here’s what you’ll need to get started.
Essential Tools and Equipment
- Mixing Bowls
- Electric Mixer
- Baking Sheets
- Parchment Paper
- Wire Rack
Importance of Each Tool
- Mixing Bowls: Essential for combining ingredients smoothly without mess.
- Electric Mixer: Helps achieve fluffy butter and sugar quickly, ensuring better cookie texture.
- Baking Sheets: Provides a sturdy surface for even baking of cookies.
- Parchment Paper: Prevents sticking and allows for easy cleanup after baking.
Ingredients
Delicious sugar cookies topped with caramelized pineapple rings, combining the flavors of classic pineapple upside down cake in a fun, handheld treat.
For the Cookie Dough
- 1 cup Unsalted Butter, softened
- 1 cup Granulated Sugar
- 1 large Egg
- 1 teaspoon Vanilla Extract
- 2 cups All-Purpose Flour
- 1 teaspoon Baking Soda
- 1/2 teaspoon Salt
For Topping
- 10-12 rings Canned Pineapple, well-drained and patted dry
- to taste Additional Sugar for Sprinkling
How to Make Pineapple Upside Down Sugar Cookies
Step 1: Preheat the Oven
Preheat your oven to 350°F (180°C) and line baking trays with parchment paper for easy cleanup.
Step 2: Cream Butter and Sugar
In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. This should take about 2-3 minutes using an electric mixer.
Step 3: Add Egg and Vanilla
Beat in one large egg and one teaspoon of vanilla extract until well combined and smooth.
Step 4: Mix Dry Ingredients
In another bowl, whisk together two cups of all-purpose flour, one teaspoon of baking soda, and half a teaspoon of salt. Gradually add this mixture to the wet ingredients, mixing just until a soft dough forms.
Step 5: Prepare Cookie Dough Mounds
Scoop about two tablespoons of dough per cookie onto the prepared baking trays. Space them about two inches apart.
Step 6: Add Pineapple Rings
Gently press one dried pineapple ring onto each mound of cookie dough, flattening slightly. If necessary, trim or halve the rings to fit better.
Step 7: Sprinkle with Sugar
Sprinkle a bit of granulated sugar over the tops of the pineapple for added sparkle and caramelization.
Step 8: Bake Cookies
Bake in your preheated oven for about 11-13 minutes or until the cookies are lightly golden around the edges but set in the center.
Step 9: Cool Down
Allow your cookies to cool on the baking tray for a few minutes before transferring them to a wire rack to cool completely. Enjoy!
How to Serve Pineapple Upside Down Sugar Cookies
Serving Pineapple Upside Down Sugar Cookies can enhance their delightful flavors and make for a memorable dessert experience. Here are some fun and creative ideas for serving these delicious treats.
Pair with Ice Cream
- Vanilla Ice Cream – The classic flavor complements the caramelized pineapple perfectly.
- Coconut Sorbet – A refreshing alternative that adds a tropical twist.
Create a Cookie Sandwich
- Cream Cheese Frosting – Spread a layer of cream cheese frosting between two cookies for added richness.
- Whipped Cream – Use whipped cream for a light and fluffy sandwich option.
Serve with Fresh Fruit
- Mixed Berries – Fresh strawberries, blueberries, or raspberries brighten the plate and add tanginess.
- Sliced Kiwi – Adds a vibrant color contrast and a hint of tartness that pairs well with cookies.
Drizzle with Chocolate
- Dark Chocolate Sauce – A rich drizzle enhances the sweetness of the cookies.
- White Chocolate Ganache – Offers a creamy counterpart to the sugary pineapple topping.

How to Perfect Pineapple Upside Down Sugar Cookies
Perfecting your Pineapple Upside Down Sugar Cookies is all about attention to detail. Follow these tips to ensure your cookies turn out delicious every time.
- Use Room Temperature Ingredients – Ensure butter and egg are at room temperature for easier mixing and better texture.
- Don’t Overmix the Dough – Mix just until combined to keep cookies soft and tender.
- Chill the Dough (Optional) – If time allows, chill the dough for 30 minutes before scooping, which helps prevent spreading.
- Adjust Baking Time – Keep an eye on your cookies; baking times may vary based on oven type and tray used.
- Experiment with Toppings – Try adding chopped nuts or different types of sugar for varied textures and flavors.
- Store Properly – Keep leftover cookies in an airtight container at room temperature to maintain freshness.
Best Side Dishes for Pineapple Upside Down Sugar Cookies
Pairing side dishes with your Pineapple Upside Down Sugar Cookies can create a delightful dessert spread. Here are some great options to consider.
- Fruit Salad – A mix of seasonal fruits balances the sweetness of the cookies beautifully.
- Chocolate Fondue – A fun dipping option that adds decadence alongside your sweet treats.
- Cheese Platter – Include mild cheeses like brie or gouda, which pair nicely with sweet flavors.
- Pineapple Chunks – Fresh pineapple enhances the theme of your dessert while providing extra juiciness.
- Coconut Macaroons – These chewy cookies complement the tropical flavor profile of your sugar cookies.
- Coffee or Tea – A warm beverage can enhance the overall experience by contrasting with the sweetness.
Common Mistakes to Avoid
Making Pineapple Upside Down Sugar Cookies can be fun, but there are a few common mistakes to watch out for.
- Using Warm Butter: Using melted or warm butter can lead to cookies that spread too much. Always use softened but cool butter for the best texture.
- Skipping the Dry Ingredients: Not properly measuring or mixing the flour, baking soda, and salt can result in uneven cookies. Always whisk dry ingredients separately before combining them with wet ingredients.
- Overbaking the Cookies: Baking too long can make cookies hard instead of soft. Keep an eye on them and remove them as soon as they are lightly golden.
- Not Draining Pineapple Properly: Excess moisture from canned pineapple can affect cookie consistency. Make sure to drain and pat dry each pineapple ring thoroughly.
- Neglecting to Chill Dough: Skipping chilling time can lead to flat cookies. If your dough feels soft, chill it for 30 minutes before scooping onto trays.

Storage & Reheating Instructions
Refrigerator Storage
- Store cookies in an airtight container for up to 5 days.
- Place parchment paper between layers to prevent sticking.
Freezing Pineapple Upside Down Sugar Cookies
- Freeze cookies in a single layer on a baking tray until solid, then transfer to a freezer bag.
- They can be stored for up to 3 months.
Reheating Pineapple Upside Down Sugar Cookies
- Oven: Preheat to 350°F (180°C) and warm cookies for about 5-7 minutes.
- Microwave: Heat one cookie at a time for about 10 seconds for a soft treat.
- Stovetop: Place in a pan over low heat covered with a lid for about 2-3 minutes.
Frequently Asked Questions
Here are some common questions about making Pineapple Upside Down Sugar Cookies.
Can I use fresh pineapple instead of canned?
Yes, you can use fresh pineapple rings! Just ensure they are well-drained and patted dry before placing on the dough.
How do I make these cookies gluten-free?
You can substitute all-purpose flour with a gluten-free flour blend that measures cup-for-cup.
What if I don’t have unsalted butter?
You can use salted butter but reduce or omit any additional salt in the recipe.
How do I customize the flavors?
Feel free to add coconut flakes or chopped nuts for extra texture and flavor within your sugar cookie dough!
Final Thoughts
These Pineapple Upside Down Sugar Cookies blend nostalgic flavors into a delightful treat. They’re perfect for sharing at gatherings or enjoying on your own. Feel free to customize them with toppings like toasted coconut or nuts for added flair. Give this fun recipe a try—your taste buds will thank you!
Pineapple Upside Down Sugar Cookies
Dive into the delightful world of Pineapple Upside Down Sugar Cookies, where classic flavors meet creative fun. These cookies offer a scrumptious twist on the beloved pineapple upside-down cake, featuring rich, buttery sugar cookies topped with caramelized pineapple rings. Perfect for any occasion—from casual snacks to festive gatherings—these treats are sure to impress family and friends alike. With their vibrant appearance and unique taste, they’ll be a hit at your next get-together!
- Prep Time: 15 minutes
- Cook Time: 13 minutes
- Total Time: 28 minutes
- Yield: Makes approximately 24 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Ingredients
- 1 cup unsalted butter (softened)
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 10-12 rings canned pineapple (well-drained)
- Additional sugar for sprinkling
Instructions
- Preheat your oven to 350°F (180°C) and line baking trays with parchment paper.
- In a mixing bowl, cream together softened butter and granulated sugar until fluffy.
- Beat in the egg and vanilla extract until fully combined.
- In another bowl, whisk together flour, baking soda, and salt; gradually mix into wet ingredients until a soft dough forms.
- Scoop about two tablespoons of dough onto prepared trays, spacing them apart.
- Press one dried pineapple ring onto each mound of dough; sprinkle with extra sugar.
- Bake for 11-13 minutes or until lightly golden around the edges.
- Allow cooling on the tray for a few minutes before transferring to a wire rack.
Nutrition
- Serving Size: 1 cookie (30g)
- Calories: 150
- Sugar: 10g
- Sodium: 80mg
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 20g
- Fiber: 0g
- Protein: 1g
- Cholesterol: 30mg






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