There’s something undeniably magical about the aroma of cookies baking in the oven, especially when they are Pineapple Upside Down Sugar Cookies. Imagine biting into a soft, chewy cookie topped with sweet caramelized pineapple and a hint of buttery goodness. delightful dessert pairing The flavors dance on your tongue like a hula dancer at a beach party, while the texture is so delightfully tender that you’ll feel like you’re indulging in a tropical vacation.
I remember the first time I baked these delightful treats for a family gathering. There was my Aunt Edna, who usually critiques everything with the sharpness of a chef’s knife, suddenly transforming into a cookie enthusiast. “These could win awards,” she declared, her mouth full of pineapple goodness. We ended up having to hide them just to save some for later! For more inspiration, check out this Cheesy Chicken Parm Soup recipe.
[info_box title=”Why You’ll Love This Recipe”] These Pineapple Upside Down Sugar Cookies are incredibly easy to make and perfect for any occasion. They combine the classic flavors of pineapple upside-down cake with a fun cookie twist. The vibrant colors and textures create an eye-catching dessert that everyone will love. Ideal for summer barbecues or cozy family gatherings, they bring smiles all around! [/info_box]
I made these cookies last week, and my friends declared it was their new favorite treat—now I’m officially the “Cookie Queen” among my circle! cheesecake cookie variation.

Essential Ingredients
Here’s what you’ll need to make this delicious dish:
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All-Purpose Flour: A must-have for structure; ensure it’s fresh for best results.
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Granulated Sugar: Sweetens the dough perfectly; opt for organic if you can.
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Unsalted Butter: Use room temperature butter for a smooth mix; it adds richness.
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Pineapple Rings: Canned or fresh; both work well but ensure they are juicy!
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Brown Sugar: For that caramel flavor; light or dark works depending on preference.
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Baking Powder: This will help your cookies rise; don’t forget to check expiration dates.
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Eggs: Helps bind everything together; use large eggs for consistency.
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Vanilla Extract: A splash adds depth to your flavor profile; use pure if possible.
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Salt: Just a pinch enhances the sweetness and balances flavors.
The full ingredients list, including measurements, is provided in the recipe card directly below.
Let’s Make it Together
Preheat Your Oven: Start by preheating your oven to 350°F (175°C). Line your baking sheets with parchment paper to prevent sticking and make cleanup easier.
Create the Topping Mixture: In a small bowl, mix brown sugar and melted butter until smooth. Spread this mixture evenly over the lined baking sheets—this will create that delightful caramel layer.
Add Pineapple Rings: Place pineapple rings on top of the brown sugar mixture. You can even cut them in half if you want smaller bites of deliciousness!
Prepare Cookie Dough: In a large mixing bowl, cream together softened butter and granulated sugar until fluffy. Beat in eggs one at a time and add vanilla extract for flavor.
Mix Dry Ingredients: In another bowl, whisk together flour, baking powder, and salt. Gradually add this dry mixture to your wet mixture until just combined—don’t overmix!
Scoop and Bake Cookies: Drop spoonfuls of dough over each pineapple ring on your baking sheets. Bake in preheated oven for 12-15 minutes or until edges look golden brown.
Let these beauties cool on wire racks before diving in—you’ll want to savor every bite when they come out warm!
Now you’re ready to wow your friends and family with these delightful Pineapple Upside Down Sugar Cookies! Enjoy!
[info_box title=”You Must Know”] This delightful Pineapple Upside Down Sugar Cookies Recipe brings tropical joy to any dessert table. The combination of sweet, buttery cookies topped with caramelized pineapple creates a treat that’s both nostalgic and innovative. Perfect for summer barbecues or cozy family gatherings, it’s sure to impress. [/info_box]
Perfecting the Cooking Process
Start by creaming the butter and sugar until light and fluffy, then incorporate eggs before mixing in dry ingredients. This sequence ensures a smooth batter and delightful texture in your cookies.

Add Your Touch
Consider adding a sprinkle of coconut or chopped macadamia nuts for an extra tropical twist. You can also use brown sugar instead of white for deeper flavor.
Storing & Reheating
Store your cookies in an airtight container at room temperature for up to a week. If you want to enjoy them warm, pop them in the microwave for 10-15 seconds.
[info_box title=”Chef’s Helpful Tips”] Always use fresh pineapple for the best flavor; canned varieties can be too soft. Ensure your butter is at room temperature for easy creaming. Don’t overbake; these cookies should be soft in the center! [/info_box]
I recall the first time I made these cookies; my friends devoured them within minutes, leaving me with just crumbs to savor. perfect pairing with pineapple savory chicken sandwich.

FAQ
Can I use canned pineapple for this recipe?
Yes, but fresh pineapple offers better texture and flavor.
How do I know when the cookies are done?
Cookies should be lightly golden around the edges but soft in the middle.
Can I freeze these cookies?
Absolutely! Freeze them in an airtight container for up to three months.
Pineapple Upside Down Sugar Cookies
- Total Time: 30 minutes
- Yield: Approximately 24 cookies 1x
Description
Experience a taste of paradise with these Pineapple Upside Down Sugar Cookies! Soft, chewy cookies topped with caramelized pineapple create a delightful blend of flavors and textures that will transport you to a sunny beach. Perfect for summer gatherings or cozy family evenings, these cookies are sure to become a favorite treat!
Ingredients
- 2 cups all-purpose flour
- 1 cup granulated sugar
- 1/2 cup unsalted butter (softened)
- 1 cup pineapple rings (fresh or canned)
- 1/2 cup brown sugar
- 1 tsp baking powder
- 2 large eggs
- 1 tsp vanilla extract
- 1/4 tsp salt
Instructions
- Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper.
- In a small bowl, combine brown sugar and melted butter; spread evenly on lined sheets.
- Place pineapple rings on top of the brown sugar mixture.
- In a large bowl, cream softened butter and granulated sugar until fluffy. Add eggs one at a time and mix in the vanilla.
- In another bowl, whisk together flour, baking powder, and salt. Gradually add to the wet mixture until just combined.
- Drop spoonfuls of dough onto each pineapple ring and bake for 12-15 minutes until edges are golden brown.
- Cool on wire racks before serving.
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: Tropical
Nutrition
- Serving Size: 1 cookie (30g)
- Calories: 150
- Sugar: 10g
- Sodium: 60mg
- Fat: 6g
- Saturated Fat: 3g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 22g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 20mg




