Name: Pineapple Upside-Down Sugar Cookies: A Sweet Tropical Escape
Prep time: 30 min
Cook time: 15 min
Total time: 60 min
Ingredients: 1/2 cup Butter (softened); 1 cup Granulated Sugar; 1 large Egg (or flax egg for vegan); 1 1/2 cups All-Purpose Flour (or gluten-free mix); 1 teaspoon Baking Powder; 1/4 teaspoon Salt; 6 slices Canned Pineapple Slices (or fresh pineapple); 6 pieces Maraschino Cherries (or fresh cherries); 4 tablespoons Butter (for melting); 1/2 cup Brown Sugar

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A warm breeze wraps around me as I peel back the lid of a vintage recipe box, revealing scattered notes filled with cherished memories and flavors. Among them, the recipe for Pineapple Upside-Down Sugar Cookies catches my eye, promising a delightful tropical twist that captivates both young and old. These cookies are not only incredibly easy to make, but they also transform ordinary gatherings into sweet celebrations with their vibrant presentation. With a rich, chewy base adorned by glossy caramelized pineapple and cherries, every bite is a mini vacation for your taste buds. Whether you serve them at a party or indulge in them by yourself, these cookies blend nostalgia and creativity, ensuring that homemade sweetness triumphs over any fast food option. Have you ever tried turning a classic dessert into a cookie? Join me on this delicious journey!

Why You’ll Love Pineapple Upside-Down Cookies

Tropical Twist: These cookies infuse the classic upside-down cake flavor into a portable treat, ensuring everyone can enjoy a taste of the tropics.
Easy to Make: With straightforward steps, this recipe is perfect for both novice bakers and seasoned chefs seeking a quick dessert option.
Perfect for Gatherings: Brighten up any get-together or potluck; their eye-catching presentation and sweet aroma will have guests asking for the recipe!
Versatile Toppings: Feel free to customize; try using fresh fruits or add a sprinkle of toasted coconut for an extra burst of flavor.
Chewy & Delicious: The delightful combination of caramelized pineapple and cherries atop a soft cookie base makes every bite memorable.
Nostalgic Flavor: These cookies combine childhood memories of baking with new flavors, serving as a delicious reminder of simpler times.

If you loved this flavorful experience, be sure to check out our Mango Cookies Delightful for another sweet treat that fills your kitchen with warmth!

Pineapple Upside-Down Sugar Cookies Ingredients

• Get ready for a delightful treat!

For the Cookie Base

Butter – Adds richness and softness; make sure it’s softened for easy creaming.
Granulated Sugar – Provides sweetness and structure; you can use brown sugar for extra moisture.
Egg – Binds ingredients, providing moisture; a flax egg works great as a vegan substitute.
Flour – The main component for structure; all-purpose is standard, but a gluten-free mix can shine too.
Baking Powder – Helps the cookies rise; don’t skip this essential ingredient.
Salt – Enhances flavor; it’s a tiny ingredient that makes a huge difference!

For the Topping

Canned Pineapple Slices – Essential for sweetness and moisture; fresh pineapple can add a zingy twist.
Maraschino Cherries – Add a pop of color and sweetness; opt for fresh cherries for a natural touch.

Dive into the joy of baking these Pineapple Upside-Down Sugar Cookies, and let their tropical flavor whisk you away!

Step‑by‑Step Instructions for Pineapple Upside-Down Sugar Cookies

Step 1: Prepare the Topping
In a medium skillet over low heat, melt 4 tablespoons of butter along with 1/2 cup of brown sugar until bubbly, stirring frequently. Next, arrange 6 pineapple slices and 6 maraschino cherries in the skillet, pressing them gently into the mixture. Allow this to cook for about 4 minutes until the pineapple is slightly tender and the sugar has caramelized, creating a delightful base for your Pineapple Upside-Down Sugar Cookies.

Step 2: Make the Cookie Dough
In a large mixing bowl, cream together 1/2 cup softened butter and 1 cup granulated sugar until light and fluffy, about 3-4 minutes. Add in 1 egg and mix until fully incorporated. In a separate bowl, whisk 1 1/2 cups of all-purpose flour, 1 teaspoon baking powder, and 1/4 teaspoon salt, then gradually combine this dry mixture into the wet ingredients until just blended, ensuring a soft dough for the cookies.

Step 3: Assemble the Cookies
Carefully spoon generous tablespoons of the cookie dough over the arranged pineapple and cherries in the skillet, covering them evenly. Ensure the dough slightly overlaps the fruit but allows some of the topping to peek through for a beautiful presentation. This layering will create the delightful contrast of chewy cookie and sweet fruit once baked, making your Pineapple Upside-Down Sugar Cookies a showstopper.

Step 4: Bake
Preheat your oven to 350°F (175°C) and once heated, place the skillet on the middle rack. Bake the cookies for 12-15 minutes, or until they turn golden brown and slightly puffed. Keep an eye on them, as the edges should be firm while the center remains soft. You’ll know they’re done when you can smell the aromatic blend of caramelized pineapple and buttery cookie!

Step 5: Cool and Serve
Once baked, remove the skillet from the oven and let it cool for about 5 minutes. Gently slide a spatula around the edges to loosen the cookies before inverting the skillet onto a serving platter. Allow them to cool for an additional 10 minutes, giving the flavors time to meld beautifully. Serve warm, and let the tropical goodness of your Pineapple Upside-Down Sugar Cookies shine at your next gathering!

Pineapple Upside-Down Sugar Cookies Variations

Feel free to let your creativity shine with these delightful twists on the classic recipe!

Fresh Pineapple: Swap canned pineapple for fresh slices for a burst of vibrant flavor.
The freshness not only enhances the taste but also brings a lovely texture that’s wonderful with the chewy cookie base.
Peach Paradise: Try replacing pineapple with canned peaches for a juicy summer treat.
With their sweet, syrupy goodness, these cookies will take you to a sunny day at the orchard.
Tropical Coconut: Add a sprinkle of toasted coconut on top right before baking for a crunchy texture.
This small touch elevates the tropical theme, making your cookies extra special.
Berry Bliss: Substitute cherries with fresh or frozen berries such as raspberries or blueberries for a colorful twist.
The tartness from the berries beautifully balances the sweetness of the cookie, making each bite exciting!
Vegan Version: Use a flax egg instead of a regular egg and coconut oil for butter.
This swap makes your cookies accessible to a wider audience while keeping them deliciously moist.
Spiced Delight: Incorporate spices like cinnamon or nutmeg into the cookie dough for extra warmth.
These flavors harmonize beautifully with the tropical fruit, creating a delightful dance of sweetness and spice.
Nutty Crunch: Fold in some chopped pecans or walnuts to the cookie dough before baking.
The nuts bring a satisfying crunch that contrasts wonderfully with the soft texture of the cookies.
Chill Options: For a fun twist, try chilling the dough for an hour before baking to enhance flavors.
Chilling allows the dough to firm up, leading to cookies with a delightful chewy texture that’s hard to resist.

These variations allow you to explore new flavors and make this recipe your own! If you love this tropical twist, you might also enjoy our delightful Mango Cookies Delightful.

Storage Tips for Pineapple Upside-Down Sugar Cookies

Room Temperature: Store cookies in an airtight container at room temperature for up to 3 days to keep them soft and fresh.

Fridge: You can refrigerate these cookies for up to a week. Make sure they’re in an airtight container to prevent them from drying out.

Freezer: Freeze cookies for up to 3 months. Place them in a single layer on a baking sheet to freeze, then transfer to an airtight container.

Reheating: To restore softness, reheat the cookies in the oven at 350°F (175°C) for about 5 minutes, or until warm. Enjoy your delicious Pineapple Upside-Down Sugar Cookies!

What to Serve with Pineapple Upside-Down Sugar Cookies

These delightful cookies invite a symphony of flavors that transform any occasion into a tropical celebration.

Vanilla Ice Cream: Adds a creamy contrast to the chewy cookies, making each bite a blissful experience. A scoop atop a warm cookie can take you on a mini vacation.
Coconut Whipped Cream: Light and fluffy, this topping enhances the tropical feel, offering a sweet and airy complement to the rich cookies. It’s perfect for those hot summer days.
Tropical Fruit Salad: Bursting with fresh pineapple, mango, and kiwi, a fruit salad brings a refreshing brightness to balance the sweetness of the cookies. The colorful mix adds vibrancy to your dessert table.
Espresso or Coffee: The rich, bold flavors of a cup of coffee or espresso cut through the sweetness, creating a delightful contrast while enhancing your dessert experience.
Pineapple Mojito: This refreshing cocktail, with its minty notes and citrusy zing, pairs beautifully with the tropical vibes of the cookies, making for an ideal party drink.
Chocolate Dipping Sauce: A rich chocolate sauce drizzled over cookies invites indulgence, marrying the flavors of caramelized fruit with decadent chocolate bliss.
Toasted Coconut Flakes: Sprinkle them on top of the cookies for added texture and a burst of coconut flavor, taking the tropical experience to the next level.
Mango Sorbet: Light and fruity, sorbet is the perfect palate cleanser between bites, offering a cool refreshment that complements the cookies’ sweetness wonderfully.
Almond Milk: A glass of almond milk brings a nutty undertone that pairs surprisingly well with these cookies. It’s a delightful option for a comforting snack.

Make Ahead Options

These Pineapple Upside-Down Sugar Cookies are perfect for meal prep enthusiasts looking to save time! You can prepare the cookie dough up to 3 days in advance; simply wrap it tightly in plastic wrap and refrigerate. Additionally, you can also assemble the topping (butter, brown sugar, pineapple, and cherries) in the skillet, cover it, and let it sit in the fridge for up to 24 hours before baking. This way, you’re ready to pop them in the oven directly when it’s time to serve. Just remember to bring the skillet back to room temperature before baking for best results. By prepping ahead, you’ll enjoy delicious homemade cookies with minimal effort on busy weeknights!

Expert Tips for Pineapple Upside-Down Sugar Cookies

Room Temperature Butter: Ensure your butter is at room temperature for easy creaming with sugar, achieving that light, fluffy texture essential for perfect Pineapple Upside-Down Sugar Cookies.
Don’t Overmix: Mix the dough until just combined. Overmixing after adding the flour can lead to tough cookies, so be gentle!
Pan Choice: A cast-iron skillet works wonders for even baking, but any oven-safe skillet will do. Just be mindful of temperature variations!
Fruit Placement: Press the pineapple and cherries gently into the sugar mixture; this caramelizes them better, enhancing flavor when topped on your cookies.
Cool on Wire Rack: Let cookies cool on a wire rack, which helps maintain their chewy texture and prevents them from becoming soggy.

Pineapple Upside-Down Sugar Cookies Recipe FAQs

How do I choose the best pineapple for the topping?
Absolutely! When selecting canned pineapple, look for slices packed in juice or light syrup rather than heavy syrup for a better balance of sweetness and flavor. If using fresh pineapple, choose one that is golden and fragrant, with no dark spots or softness, indicating ripeness. Fresh pineapple will add a more vibrant taste to your cookies!

What is the best way to store Pineapple Upside-Down Sugar Cookies?
To keep your cookies fresh and chewy, store them in an airtight container at room temperature for up to 3 days. If you want to extend their life, refrigerate them for up to a week or freeze for up to 3 months. Just make sure to wrap them well before freezing to avoid freezer burn!

Can I freeze Pineapple Upside-Down Sugar Cookies?
Yes, you can! To freeze, first, cool the cookies completely. Then lay them in a single layer on a baking sheet until frozen solid. After that, transfer them to an airtight container or a freezer bag, separating layers with parchment paper to prevent sticking. They will stay delicious for up to 3 months!

What should I do if my cookies turn out too chewy or tough?
If your cookies are too chewy or tough, you might have overmixed the dough after adding the flour, which can develop gluten and lead to a denser texture. To correct this, mix just until combined. Also, make sure you’re measuring your flour accurately; using too much can affect the texture too. Light and fluffy is the goal!

Are there any dietary considerations I should keep in mind for these cookies?
Yes! For those with egg allergies or following a vegan diet, you can use a flax egg as a fantastic substitute. Just mix 1 tablespoon of ground flaxseed with 2.5 tablespoons of water, let it sit for 5 minutes, and it’s ready to use as an egg replacement. Additionally, check that your maraschino cherries are dye-free if you’re avoiding artificial colors. Enjoy these tropical treats worry-free!