Irresistible Pineapple Upside Down Cookies

Welcome to a delightful twist on a classic favorite with these Pineapple Upside Down Sugar Cookies! Imagine the perfect combination of a traditional pineapple upside-down cake and a soft, buttery cookie all in one bite. These cookies are not just a treat; they are a tropical escape in the midst of your everyday routine.

Crafted with love and nostalgia, these cookies have become a staple at my family gatherings and summer picnics. The aroma of caramelized sugar and sunshine fills the kitchen as these cookies bake to perfection. The sweet surprise of a maraschino cherry nestled in the center takes me back to cherished memories of my grandma’s Sunday cakes.

With a touch of browned butter and caramelized sugar, these cookies are a true indulgence. The recipe is versatile too – try using Greek yogurt instead of sour cream for a slight twist, or add chopped pecans or coconut for extra texture. Whether enjoyed on their own or as part of a dessert platter, these cookies are sure to steal the spotlight at any occasion.

Quick Benefits

• Soft and moist texture due to the addition of sour cream in the dough
• Caramelized brown sugar and pineapple create a rich and nostalgic flavor profile
• Versatile recipe allows for customization with different fruits or added textures like pecans or coconut
• Make-ahead option for quick, freshly baked desserts by freezing and thawing at room temperature

Why You’ll Love This Irresistible Pineapple Upside Down Cookies Recipe

• Combines classic pineapple upside-down cake flavors: Enjoy the delicious taste of a pineapple upside-down cake in cookie form, perfect for those who love the traditional dessert but want a fun twist.
• Perfect for parties and gatherings: Ideal for parties, picnics, or any occasion where you want to impress with a unique and tasty treat that stands out.
• Brings a touch of tropical flair: Experience a burst of tropical flavor with each bite, making these cookies perfect for summer or anytime you need a little taste of sunshine.
• Nostalgic and comforting: The combination of maraschino cherries, browned butter, and caramelized sugar will transport you back to fond memories of family recipes and grandma’s baking.
• Versatile and customizable: Easily adaptable with substitutions like Greek yogurt for sour cream, various fruit options, or added nuts or coconut for texture, allowing you to personalize the cookies to your taste.
• Make-ahead option: Convenient make-ahead dessert that can be frozen and enjoyed later, making it a great choice for planning ahead for gatherings or simply having a sweet treat on hand.
• Kid-friendly and individual portions: Kids and adults alike will love having their own mini pineapple upside-down cookie, making them perfect for family gatherings, game nights, or sharing with friends.
• A modern twist on a vintage favorite: A nod to the classic pineapple upside-down cake, these cookies offer a bite-sized version of a beloved vintage dessert, bringing together tradition and modern taste.

Ingredients for Irresistible Pineapple Upside Down Cookies

Cookie Dough

• 1 teaspoon cornstarch
• 2 large eggs
• 2 teaspoons vanilla extract
• 1/2 teaspoon salt
• 1 cup unsalted butter, softened
• 1 teaspoon baking powder
• 1/2 cup sour cream
• 3 cups all-purpose flour
• 1 1/2 cups granulated sugar

Topping

• 13 maraschino cherries
• 1 cup light brown sugar, packed
• 1/2 cup unsalted butter, melted
• 13 canned pineapple slices, drained

Pro Tips for Irresistible Pineapple Upside Down Cookies

For perfect Pineapple Upside Down Sugar Cookies every time, remember to drain the canned pineapple slices well to prevent excess moisture in the cookies. Layer the fruit and brown sugar mixture at the bottom of each pan cavity before adding the dough, then invert the cookies after baking to reveal the beautiful fruit topping.

To enhance the flavor and texture of your cookies, consider adding chopped pecans or coconut to the dough for extra crunch. If you’re looking to make these cookies a bit healthier, try using Greek yogurt instead of sour cream to achieve a similarly tender crumb. Additionally, feel free to experiment with different fruits like diced mango or peach rings in place of pineapple for a unique twist on this classic recipe.

For convenient make-ahead desserts, prepare the cookies as directed, then freeze them in a single layer before transferring to containers with parchment between layers. Thaw at room temperature when ready to enjoy, ensuring your treats taste freshly baked whenever you’re craving a sunny and nostalgic sweet treat.

How to Make Irresistible Pineapple Upside Down Cookies

Step 1: Preheat and Prepare Pan

Preheat the oven to 350°F (175°C) and grease a 13-cavity mini round cake pan.

Step 2: Cream Butter and Sugar

In a large mixing bowl, cream together softened butter and granulated sugar until light and fluffy.

Step 3: Mix Wet Ingredients

Combine eggs, vanilla extract, and sour cream with the butter mixture, blending until just mixed.

Step 4: Combine Dry Ingredients

Combine flour, baking powder, cornstarch, and salt until a smooth dough is formed.

Step 5: Prepare Brown Sugar Mixture

Combine melted butter and light brown sugar in a separate bowl until smooth.

Step 6: Assemble Base

Place 1 tablespoon of the brown sugar mixture into each pan cavity using a spoon.

Step 7: Add Pineapple and Cherry

Put one pineapple slice in each cavity and place a maraschino cherry in the center of each ring.

Step 8: Add Cookie Dough

Spoon 3 tablespoons of dough over each pineapple slice and gently press down to cover the fruit.

Step 9: Bake

Bake for 25 minutes, or until edges are golden brown and brown sugar mixture is bubbling.

Step 10: Cool and Unmold

Allow cookies to cool in the pan for 10 minutes, then gently turn them out onto wax paper. Adjust pineapple slices as necessary.

Step 11: Finish and Store

Cool cookies completely before serving. Store in an airtight container and consume within 2–3 days for best freshness.

Storage Tips

After making Pineapple Upside Down Sugar Cookies, store them in an airtight container at room temperature for up to three days to maintain their soft and moist texture. If you need to store them longer, place them in the refrigerator but allow them to come to room temperature before serving so the caramel can soften again. To extend their freshness, freeze the cookies in a single layer, then transfer them to containers with parchment between layers. Thaw at room temperature when you’re ready to enjoy these delightful treats.

Sour cream is a key ingredient in this recipe as it adds moisture and tenderness to the cookies, resulting in a softer and richer crumb. If you prefer, you can substitute Greek yogurt for a similar tender texture. When baking, layer the pineapple slices, cherries, and brown sugar mixture at the bottom of each pan cavity before adding the dough, and invert the cookies after baking so that the fruit tops each one. Enjoy these cookies fresh with your family or save them for later to relish that delicious caramel goodness throughout the week.

Ingredient Substitutions

If you don’t have sour cream on hand, Greek yogurt can be used as a suitable substitute in this recipe. It provides a similar level of moisture and helps create a tender crumb in the cookies. The flavor profile will remain deliciously tangy and rich, just like with sour cream.

Fresh pineapple can be a wonderful substitution for canned pineapple in this recipe, particularly when it’s in season. The fresh fruit will bring a brighter and more vibrant flavor to the cookies. Just ensure the pineapple slices are well-drained to prevent excess moisture and maintain the right texture in the final baked product.

Serving Suggestions

To elevate the presentation of these delightful Pineapple Upside Down Sugar Cookies, consider serving them on a platter adorned with tropical leaves or flowers for a vibrant touch that complements their fruity flavors. For a decadent twist, top each cookie with a dollop of whipped coconut cream and a sprinkle of toasted coconut before serving to add a creamy and tropical element that will enhance the overall dessert experience.

For a playful and interactive dessert option, set up a DIY cookie decorating station featuring bowls of toppings like chopped pecans, shredded coconut, and mini chocolate chips. Let guests customize their cookies with these delicious add-ons to create their personalized tropical treats, making it a fun and engaging activity for parties or gatherings.

FAQs for Irresistible Pineapple Upside Down Cookies

Can I use fresh pineapple instead of canned in this recipe?

Yes, fresh pineapple slices work well if cut to fit the pan. Ensure they are well-drained to prevent excess moisture.

Why is sour cream used in the cookie dough?

Sour cream adds moisture and tenderizes the cookie, resulting in a softer, richer crumb.

How should I prevent the fruit from sticking to the pan after baking?

Let the cookies cool in the pan for 10 minutes before inverting. If fruit sticks, gently reposition on top while still warm.

How should I store these Pineapple Upside Down Sugar Cookies?

Keep cookies in an airtight container at room temperature. For the best texture, enjoy within 2–3 days of baking.

Conclusion

I hope this recipe for Pineapple Upside Down Sugar Cookies brings as much joy and nostalgia to your gatherings as it has to mine. The combination of caramelized pineapple, cherries, and buttery brown sugar truly makes each bite a delightful tropical escape. Whether you’re baking these for a special occasion or just to brighten up an ordinary day, these cookies are sure to impress and satisfy.

Remember, the beauty of these Pineapple Upside Down Sugar Cookies lies not only in their delicious taste but also in the memories and stories they evoke. So, gather your loved ones, savor each bite, and create new moments to cherish. I can’t wait for you to try this recipe and experience the sweet magic of these delightful treats firsthand.