There’s something magical about the combination of buttery goodness and sweet, tropical pineapple that makes your taste buds do a happy dance. The moment you sink your teeth into a Pineapple Upside Down Sugar Cookie, you’re greeted with a burst of flavors that transports you to a sun-soaked beach, where the only worry is whether to have another cookie or take a nap. Imagine the warm aroma wafting through your kitchen, teasing your senses and promising a treat that’s both nostalgic and refreshing.
I still remember the first time I made these cookies for a summer barbecue. My friends were skeptical at first—sugar cookies with pineapple? But once they took that first bite, their eyes lit up like kids in a candy store. Now, these cookies are my go-to recipe for gatherings, perfect for when you want to impress without breaking a sweat. Get ready to experience a flavor explosion that will have everyone begging for the secret recipe! For more inspiration, check out this Thanksgiving Pecan Pie Recipe recipe.
Why You'll Love This Recipe
- These delightful cookies combine ease of preparation with an irresistible flavor profile
- The bright colors and textures create a visually stunning treat for any event
- Perfect for summer picnics or cozy family gatherings, they are versatile enough to be enjoyed year-round
- Plus, they leave you with memories of joyful moments spent with loved ones!
I’ll never forget how my friends devoured these cookies within minutes, leaving behind nothing but crumbs and wide smiles.

Essential Ingredients
Here’s what you’ll need to make this delicious dish:
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All-Purpose Flour: Essential for structure, use unbleached flour for best results that yield chewy cookies.
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Baking Soda: This leavening agent helps your cookies rise beautifully while keeping them soft inside.
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Unsalted Butter: Use room temperature butter for easy mixing and rich flavor; it enhances the cookie’s texture.
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Granulated Sugar: Adds sweetness and contributes to that lovely crisp edge everyone loves in sugar cookies.
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Brown Sugar: Incorporate light brown sugar for moisture and a hint of caramel flavor—this is key! For more inspiration, check out this Bacon Brown Sugar Chicken Tenders recipe.
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Pineapple Chunks: Fresh or canned works; just make sure they’re well-drained to avoid soggy cookies!
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Maraschino Cherries: For garnish, these little gems add a pop of color and sweetness on each cookie.
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Vanilla Extract: A splash adds depth; don’t skimp on this flavorful essential—it brings everything together!
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Eggs: Bind everything nicely; use large eggs at room temperature for optimal mixing.
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Salt: Just a pinch enhances flavors; it’s the secret ingredient that balances out sweetness perfectly.
The full ingredients list, including measurements, is provided in the recipe card directly below.
Let’s Make it Together
Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper. This ensures even baking while making cleanup a breeze.
Whisk Dry Ingredients Together: In a bowl, mix flour, baking soda, and salt until well combined. Set aside as you prepare the wet ingredients; this step helps distribute leavening evenly.
Cream Butter and Sugars: In another bowl, beat room-temperature butter with granulated and brown sugars until light and fluffy—about 3-4 minutes. This aeration creates tenderness in your cookies.
Add Eggs and Vanilla Extract: Mix in eggs one at a time along with vanilla extract until fully incorporated. You should see the mixture become creamy and fragrant at this point.
Combine Wet and Dry Mixtures: Gradually add the dry mixture into the wet one until just combined; be careful not to overmix! Gently fold in pineapple chunks—these are what make this cookie so special!
Scoop and Bake Cookies: Use a cookie scoop or tablespoon to drop dough onto prepared sheets about 2 inches apart. Top each dough ball with a maraschino cherry for that classic look before baking.
Bake them in your preheated oven for about 10-12 minutes or until golden edges form. Let them cool on wire racks before indulging in these delightful treats!
Now you’ve crafted Pineapple Upside Down Sugar Cookies that bring sunshine into every bite! Enjoy sharing them with family and friends—they won’t last long!
You Must Know
- These delightful cookies blend the tropical sweetness of pineapple with the classic comfort of sugar cookies
- The aroma fills your kitchen like a sunny beach party, making them irresistible for any gathering or a cozy night in
Perfecting the Cooking Process
To ensure even baking, start by preheating your oven to 350°F (175°C). Prepare your cookie dough while the oven warms up, and line your baking sheets with parchment paper for easy cleanup.

Add Your Touch
Feel free to swap out the crushed pineapple for diced mango or peaches for a different fruity kick. You can also sprinkle some shredded coconut on top for an extra tropical vibe.
Storing & Reheating
Store leftover cookies in an airtight container at room temperature for up to a week. Reheat them briefly in the microwave for about 10 seconds to restore their delightful softness.
Chef's Helpful Tips
- Always use fresh ingredients for the best flavor; stale ingredients lead to disappointing results
- Chill your dough before baking to enhance texture and shape
- Remember, don’t overbake – you want soft centers and slightly crisp edges
Baking these cookies reminds me of family gatherings where everyone would race to grab one fresh from the tray. The smiles on my loved ones’ faces made every moment worthwhile.

FAQ
Can I use fresh pineapple instead of canned?
Yes, but make sure it’s finely chopped and well-drained to avoid excess moisture.
What should I do if my dough is too sticky?
Chill it in the refrigerator for about 30 minutes before shaping into cookies.
How do I know when my cookies are done baking?
Look for golden edges while keeping the centers soft and slightly underbaked; they’ll firm up as they cool.
Pineapple Upside Down Sugar Cookies
- Total Time: 27 minutes
- Yield: Approximately 24 cookies 1x
Description
Pineapple Upside Down Sugar Cookies are a delightful twist on the classic sugar cookie, merging buttery sweetness with vibrant pineapple flavors. These cookies are easy to make and perfect for summer gatherings or cozy family nights. Each bite delivers a burst of tropical goodness, making them an instant favorite. With maraschino cherries on top, they not only taste amazing but also look stunning on any dessert platter. Get ready to impress your friends and family with this irresistible treat!
Ingredients
- 2 1/4 cups all-purpose flour
- 1 tsp baking soda
- 1/2 tsp salt
- 3/4 cup unsalted butter, softened
- 1/2 cup granulated sugar
- 1 cup brown sugar, packed
- 2 large eggs (room temperature)
- 2 tsp vanilla extract
- 1 cup pineapple chunks (well-drained)
- Maraschino cherries for garnish
Instructions
- Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper.
- In a bowl, whisk together flour, baking soda, and salt; set aside.
- In another bowl, cream together softened butter, granulated sugar, and brown sugar until light and fluffy.
- Beat in eggs one at a time along with vanilla extract until well combined.
- Gradually add dry ingredients to the wet mixture until just combined; fold in pineapple chunks gently.
- Drop rounded tablespoons of dough onto prepared baking sheets about 2 inches apart and top each with a maraschino cherry.
- Bake for 10-12 minutes until edges are golden; let cool on wire racks.
- Prep Time: 15 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie (30g)
- Calories: 150
- Sugar: 10g
- Sodium: 90mg
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 20g
- Fiber: <1g
- Protein: <1g
- Cholesterol: 20mg




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