There’s a special kind of joy that comes from the first bite of a warm cookie, especially when it’s a delightful twist on a classic, like these Pineapple Upside-Down Sugar Cookies. It all started one sunny afternoon when I had a craving for something sweet yet nostalgic, and I rummaged through my pantry for inspiration. The sweet tang of pineapple paired with the buttery richness of sugar cookies felt like a match made in dessert heaven.
Imagine the moment you pull these cookies out of the oven golden edges, bubbling with brown sugar, and topped with vibrant pineapple and a cherry, they are not just cookies; they are a showstopper! Perfect for gatherings or just a cozy night at home, this recipe checks all the boxes: it’s easy to make, visually stunning, and bursting with flavor. Let me take you through the steps to create this sweet delight that will surely impress your family and friends, making your kitchen the go-to place for dessert lovers.
Why love Pineapple Upside Down Sugar Cookies?
Deliciously Unique: These cookies bring a playful twist to traditional sugar cookies, making them a standout treat.
Visual Appeal: Each cookie showcases glossy pineapple slices and vibrant cherries, ensuring they’ll steal the show at any dessert table.
Perfectly Balanced: The sweet, buttery flavor pairs wonderfully with the tangy pineapple, creating a delicious medley that excites the palate.
Easy to Make: With straightforward steps, you’ll enjoy baking these cookies without the fuss, perfect for both novice and seasoned bakers.
Crowd-Pleaser: Whether for a potluck or a family gathering, these cookies are sure to impress and bring smiles to everyone’s faces.
Pineapple Upside Down Sugar Cookie Ingredients
For the Cookie Dough
• 1 cup butter – Ensure it’s softened for easy mixing to achieve that light, fluffy texture.
• 1 1/2 cups granulated sugar – Adds sweetness and helps create a soft cookie structure.
• 2 eggs – Binds the ingredients together while providing moisture.
• 2 tsp. vanilla extract – Enhances the overall flavor profile of the cookies.
• 1/2 cup sour cream – Keeps the cookies moist and adds a slight tang.
• 3 cups all-purpose flour – The foundation of our Pineapple Upside Down Sugar Cookies for perfect dough consistency.
• 1 tsp. baking powder – Helps the cookies rise and remain soft.
• 1 tsp. cornstarch – Ensures a tender, melt-in-your-mouth texture.
• 1/2 tsp. salt – Balances sweetness and enhances the overall flavor.
For the Topping
• 13 canned pineapple slices – These are the stars of your cookies, offering lovely sweetness and a tropical note.
• 13 maraschino cherries – Adds a pop of color and sweetness right in the center of each cookie.
• 1/2 cup butter, melted – Creates a luscious base for the pineapple and brown sugar.
• 1 cup light brown sugar, packed – Gives a caramel-like flavor that will bubble and create a delightful glaze as they bake.
Get ready to create these Pineapple Upside Down Sugar Cookies that will enchant your taste buds and bring joy to your kitchen!
How to Make Pineapple Upside Down Sugar Cookies
- Preheat your oven to 350°F (175°C). Get your USA pan mini round cake pan ready by setting it aside; this will be the perfect shape for our delightful cookies.
- Cream together the butter and granulated sugar in a large mixing bowl until the mixture is light and fluffy. This should take about 3-4 minutes; the air incorporated will make your cookies soft!
- Incorporate the eggs, vanilla extract, and sour cream into the bowl, mixing until everything is well combined and creamy. The sour cream adds a nice tangy flavor and keeps the dough moist.
- Combine the flour, baking powder, cornstarch, and salt in another bowl. Gradually add this dry mixture to the wet ingredients, mixing until the cookie dough just comes together. Don’t over-mix; we want it tender!
- Mix the melted butter and brown sugar in a separate bowl until fully combined. This delicious mix will create a gooey base for the toppings.
- Distribute about a tablespoon of the brown sugar mixture into the bottom of each cavity in your pan, ensuring it covers the bottom evenly. This creates the signature caramel-like topping.
- Top each brown sugar layer with a pineapple slice, placing a maraschino cherry right in the center. This step not only enhances flavor but adds a vibrant, inviting look!
- Add a 3 T. scoop of cookie dough on top of each pineapple slice. Use an offset spatula to smooth out the dough, making sure it covers the pineapple nicely.
- Bake the cookies in your preheated oven for about 25 minutes. Monitor them until the edges are golden brown and the brown sugar mixture is bubbling delightfully around the sides.
- Cool for 10 minutes right in the pan, then carefully turn them out onto a wax paper-covered surface. If a pineapple slice sticks, gently reposition it back on the cookie.
- Let cool completely before indulging! Store any leftovers in an airtight container to keep them fresh and tasty.
Optional: Drizzle with a bit of melted chocolate for an extra treat!
Exact quantities are listed in the recipe card below.
How to Store and Freeze Pineapple Upside Down Sugar Cookies
Room Temperature: Keep cookies covered at room temperature for up to 3 days. They’ll stay soft and delicious—perfect for quick snacking!
Fridge: For extended freshness, store them in an airtight container in the fridge for up to 1 week. This helps preserve the flavor and texture.
Freezer: These cookies can be frozen for up to 3 months. Just ensure they’re wrapped tightly to prevent freezer burn, and thaw before enjoying.
Reheating: Warm them in the microwave for a few seconds or pop them in the oven at 350°F (175°C) for a couple of minutes to revive their freshness!
Tips for the Best Pineapple Upside Down Sugar Cookies
Room Temperature Ingredients: Ensure all ingredients, especially butter and eggs, are at room temperature for better incorporation and a smoother dough.
Don’t Overmix: When combining wet and dry ingredients, mix just until combined. Overmixing can lead to tough cookies, so be gentle.
Pan Preparation: Generously coat your USA pan mini round cake pan with non-stick spray or butter to prevent sticking and make removal easier.
Cooling Time: Allow cookies to cool slightly in the pan before transferring them. This prevents breakage and keeps the pineapple topping intact.
Storage Tips: Store your Pineapple Upside Down Sugar Cookies in an airtight container to maintain their soft texture and vibrant flavors for days.
Pineapple Upside Down Sugar Cookies Variations
Feel free to jazz up your cookies with these delightful twists that promise to bring even more joy to your baking!
- Gluten-Free: Use a 1:1 gluten-free flour blend instead of all-purpose flour for a delicious alternative.
- Coconut Twist: Add 1/2 cup of shredded coconut to the dough for a tropical flavor that complements the pineapple perfectly.
- Spiced Up: Mix in 1 tsp of cinnamon or nutmeg to the dry ingredients for a warm, cozy spice that elevates the sweetness.
- Vegan-Friendly: Substitute the butter with vegan butter and the eggs with flax eggs (1 tbsp ground flaxseeds + 2.5 tbsp water) for a plant-based treat.
- Chocolate Drizzle: Melt dark or white chocolate and drizzle it over the cooled cookies for an elegant finish that adds a touch of decadence.
- Pineapple Variation: Try using fresh pineapple chunks instead of canned slices for a fresher taste and a firmer texture.
- Nutty Crunch: Incorporate 1/2 cup of chopped pecans or walnuts into the dough for a delightful crunch that adds depth to each bite.
- Berry Bliss: Replace the maraschino cherries with fresh raspberries or strawberries that complement the pineapple’s sweetness beautifully.
Embrace these variations to create your own signature delicious cookie, perfect for every taste and occasion!
What to Serve with Pineapple Upside Down Cookies?
Imagine the delightful aroma of freshly baked cookies wafting through your home, making every gathering feel extra special.
- Vanilla Ice Cream: A classic pairing, the creamy richness of vanilla ice cream perfectly complements the sweet, tropical flavors of the cookies.
- Fresh Fruit Salad: A medley of berries and citrus adds a refreshing balance to the cookies’ sweetness, providing a bright, colorful contrast on your plate.
- Coconut Whipped Cream: Light and airy, this tropical twist enhances the cookie’s flavor profile with a silky texture, making each bite even more indulgent.
- Coffee or Espresso: A warm cup of coffee brings out the caramel notes in the cookies, creating a delightful sensory experience that’s comforting and satisfying.
- Pineapple Rum Punch: Enhance that tropical vibe with a fruity drink that echoes the flavors of the cookies, making for a fun and festive pairing.
- Chocolate Drizzle: Elevate your cookies with a simple chocolate drizzle for a rich, decadent finish that balances out the sweetness beautifully.
- Toasted Coconut Flakes: Adding these on top or alongside the cookies provides a crunchy texture that contrasts with the soft interior, introducing a delightful flavor twist.
- Lemonade: A tangy glass of lemonade will cut through the cookies’ sweetness while providing a refreshing citrus zing, perfect for warm days.
- Chocolate-Covered Pineapple Bites: Keep the pineapple theme going with these treats, adding an extra layer of flavor and richness on the dessert table.
Make Ahead Options
These Pineapple Upside Down Sugar Cookies are perfect for meal prep, allowing busy home cooks to savor the joy of homemade treats without the last-minute rush! You can prepare the cookie dough up to 24 hours in advance by mixing all the ingredients and storing it tightly wrapped in the refrigerator. Additionally, you can layer the brown sugar and pineapple slices in the pan and cover with plastic wrap, letting it sit in the fridge overnight. When you’re ready to bake, simply scoop the chilled dough on top of the prepared fruit and bake directly from the fridge for delicious results just as good as freshly made! Enjoy the time savings while impressing loved ones with these delightful cookies!
Pineapple Upside Down Sugar Cookies Recipe FAQs
How do I choose ripe pineapples for this recipe?
Absolutely! For a sweeter and juicier flavor, look for canned pineapple slices that are light yellow and free from dark spots. If you’re using fresh pineapple, choose ones that yield slightly to pressure and have a sweet aroma.
How should I store leftover cookies?
You can keep these delightful cookies covered at room temperature for up to 3 days! For longer freshness, place them in an airtight container in the fridge, where they’ll stay tasty for about a week.
Can I freeze Pineapple Upside Down Sugar Cookies?
Very! To freeze, allow the cookies to cool completely. Then, wrap each cookie tightly with plastic wrap or aluminum foil, and place them in a freezer-safe zip-top bag. They can be stored in the freezer for up to 3 months. When you’re ready to enjoy, simply thaw them at room temperature or warm them up in the oven at 350°F (175°C) for a few minutes!
What if the cookies stick to the pan?
No worries! If pineapple slices stick to your pan after baking, gently reposition them back onto the cookie using a spatula. It happens to the best of us! To prevent this in the future, make sure to generously grease your pan with non-stick spray or butter before adding the brown sugar mixture.
Are these cookies safe for pets?
Great question! While pineapple is generally safe for dogs in small amounts, the added sugar and cherries can be harmful. It’s best to keep these cookies out of your pet’s reach to ensure their safety and well-being.
How can I adjust the recipe for gluten-free needs?
To make these Pineapple Upside Down Sugar Cookies gluten-free, substitute the all-purpose flour with a gluten-free flour blend that measures 1:1. Ensure all your other ingredients, like baking powder and vanilla extract, are also gluten-free to keep the recipe safe for those with gluten intolerance. Happy baking!
Bake Irresistible Pineapple Upside Down Sugar Cookies Today
Ingredients
Equipment
Method
- Preheat your oven to 350°F (175°C). Get your USA pan mini round cake pan ready.
- Cream together the butter and granulated sugar until light and fluffy, about 3-4 minutes.
- Incorporate the eggs, vanilla extract, and sour cream into the bowl, mixing until well combined.
- Combine flour, baking powder, cornstarch, and salt in another bowl. Gradually add this dry mixture to the wet ingredients.
- Mix the melted butter and brown sugar until fully combined.
- Distribute about a tablespoon of the brown sugar mixture into the bottom of each cavity in your pan.
- Top each brown sugar layer with a pineapple slice and add a maraschino cherry in the center.
- Add a 3 T. scoop of cookie dough on top of each pineapple slice and smooth out the dough.
- Bake the cookies in the preheated oven for about 25 minutes until golden brown.
- Cool for 10 minutes in the pan, then carefully turn them out onto a wax paper-covered surface.
- Let cool completely before indulging!