There’s something utterly delightful about the aroma of freshly baked cookies wafting through the house. Imagine biting into a soft, chewy Pineapple Upside Down Sugar Cookie, where the sweet tang of pineapple dances with hints of buttery goodness and brown sugar. Your taste buds will do a happy jig as you savor each bite, making this treat perfect for any occasion, whether it’s a casual family gathering or a fancy tea party.
Growing up, my grandma had a knack for creating unexpected delights in the kitchen. One summer afternoon, she surprised us all with her version of Pineapple Upside Down Cake transformed into cookies. The laughter and joy we shared while devouring those warm delights left an imprint on my heart—and my stomach! Now, it’s your turn to create some cookie magic!
Why You'll Love This Recipe
- These Pineapple Upside Down Sugar Cookies are surprisingly easy to make and perfect for any occasion
- Their tropical flavor will transport you to a sunny beach with every bite
- Visually stunning with their vibrant colors, they are sure to impress your guests
- Plus, they are versatile enough to be enjoyed at picnics or cozy nights in
I remember the first time I made these cookies; my friends couldn’t believe how delicious they were!

Essential Ingredients
Here’s what you’ll need to make this delicious dish:
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Unsalted Butter: Use softened butter for that rich flavor and perfect texture in your cookies.
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Sugar: Granulated sugar adds sweetness; feel free to experiment with brown sugar for deeper flavor.
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Brown Sugar: Light or dark brown sugar adds moisture and caramel notes that complement the pineapple beautifully.
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Eggs: Use large eggs; they help bind everything together and add richness.
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Vanilla Extract: Pure vanilla extract enhances the cookie’s overall flavor profile—trust me on this one!
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Pineapple Chunks: Fresh or canned pineapple works; just ensure they’re well-drained if using canned.
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Flour: All-purpose flour is ideal for achieving that tender cookie texture.
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Baking Soda & Baking Powder: These leaveners give your cookies that perfect lift—don’t skip them!
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Salt: A pinch of salt elevates all flavors, balancing the 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). Line two baking sheets with parchment paper so your cookies won’t stick.
Mixing the Dough: In a large mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until fluffy. You want it light and airy—like clouds on a sunny day!
Add Eggs & Vanilla: Beat in the eggs one at a time and pour in that heavenly vanilla extract. The mixture should look smooth and gloriously creamy.
Incorporate Pineapple: Gently fold in the pineapple chunks until they’re evenly distributed throughout that luscious dough. You should see bits of sunshine peeking through!
Sift Dry Ingredients: In a separate bowl, whisk together flour, baking soda, baking powder, and salt. Gradually add this dry mix into your wet ingredients until combined—don’t overmix; we want soft cookies here.
Scoop & Bake: Using a cookie scoop or spoon, drop dough onto prepared baking sheets about 2 inches apart. Bake for 10-12 minutes until edges are lightly golden but centers still look soft.
After baking, let them cool on the sheet for about five minutes before transferring them to a wire rack. This way they’ll set up nicely without turning into crumbly messes!
And there you have it! Your very own batch of Pineapple Upside Down Sugar Cookies ready to delight taste buds! Enjoy warm or store them in an airtight container at room temperature for later snacking—if they last that long!
You Must Know
- Pineapple Upside Down Sugar Cookies are a delightful twist on a classic dessert
- The sweet and tangy pineapple pairs perfectly with the buttery cookie base, making every bite a tropical adventure
- These cookies are perfect for parties or just because you deserve a treat!
Perfecting the Cooking Process
Start by creaming butter and sugar until fluffy, then mix in eggs and vanilla. Add dry ingredients gradually for a smooth dough, ensuring even mixing.

Add Your Touch
Feel free to swap the pineapple for other fruits like peaches or cherries. Experimenting with spices like cinnamon can also elevate the flavor profile dramatically.
Storing & Reheating
Store cookies in an airtight container at room temperature for up to a week. Reheat leftovers in the microwave for about 10 seconds to regain softness.
Chef's Helpful Tips
- Use fresh pineapples for better flavor; canned ones may lack the zing you want
- Ensure cookie dough is chilled before baking to prevent spreading too much
- Always test one cookie first to adjust baking time if needed!
Memories of baking these cookies always make me smile; my friends devoured them at my last party, asking for the recipe seconds after their first bite!

FAQ
Can I use canned pineapple for this recipe?
Yes, canned pineapple works but fresh offers better flavor and texture.
How long do these cookies stay fresh?
These cookies can last up to one week when stored properly in an airtight container.
Can I freeze Pineapple Upside Down Sugar Cookies?
Absolutely! Freeze them in a single layer, then store in an airtight container for up to three months.
Pineapple Upside Down Sugar Cookies
- Total Time: 27 minutes
- Yield: Approximately 24 cookies 1x
Description
Indulge in the tropical delight of Pineapple Upside Down Sugar Cookies, a fun twist on the classic cake. These soft, chewy cookies blend the sweet-tangy flavor of pineapple with buttery richness and brown sugar, creating a treat that’s perfect for any occasion—from family gatherings to elegant tea parties. With easy-to-follow instructions and simple ingredients, you can create cookie magic that will impress your guests and satisfy your cravings!
Ingredients
- 1 cup unsalted butter (softened)
- 1 cup granulated sugar
- 1/2 cup brown sugar (light or dark)
- 2 large eggs
- 2 tsp vanilla extract
- 1 cup pineapple chunks (fresh or canned, well-drained)
- 2 1/2 cups all-purpose flour
- 1 tsp baking soda
- 1 tsp baking powder
- 1/4 tsp salt
Instructions
- Preheat oven to 350°F (175°C) and line baking sheets with parchment paper.
- In a large bowl, cream together softened butter, granulated sugar, and brown sugar until fluffy.
- Beat in eggs one at a time, followed by vanilla extract.
- Gently fold in pineapple chunks until well-distributed.
- In a separate bowl, whisk together flour, baking soda, baking powder, and salt; gradually add to wet ingredients until just combined.
- Drop dough by tablespoonfuls onto prepared baking sheets, spacing them about 2 inches apart.
- Bake for 10-12 minutes until edges are lightly golden and centers remain soft. Cool on sheets for five minutes before transferring to wire racks.
- Prep Time: 15 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 serving
- Calories: 150
- Sugar: 10g
- Sodium: 80mg
- Fat: 8g
- Saturated Fat: 5g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 19g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 25mg

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