If you have a soft spot for nostalgic flavors with a fun, unexpected twist, you are going to adore this Pineapple Upside Down Sugar Cookies Recipe. It takes the classic charm of pineapple upside down cake and transforms it into a delightful bite-sized treat, complete with tender sugar cookie dough embracing caramelized pineapple and cherries. Every single cookie brings a burst of buttery sweetness with just the right hint of tangy fruit, making them absolutely irresistible for any occasion. Trust me, once you try these, they will instantly become a favorite in your baking rotation.
Ingredients You’ll Need
All the ingredients in this Pineapple Upside Down Sugar Cookies Recipe are straightforward staples, but each one plays a crucial role in crafting that perfect balance of flavors and textures. From rich butter to fluffy eggs, and from tangy sour cream to sweet brown sugar, every component adds a unique nuance that together makes these cookies sing.
- 1 cup butter, room temperature: Ensures a soft, luscious cookie base with rich flavor and tender crumb.
- 1 ½ cups granulated sugar: Adds the classic sweet foundation that caramelizes slightly for that perfect cookie crust.
- 2 eggs: Provide structure and moisture, making the dough cohesive and soft.
- 2 tsp vanilla extract: Enhances the overall sweetness with warm, fragrant undertones.
- ½ cup sour cream: Brings tangy moisture that keeps cookies tender and adds depth to flavor.
- 3 cups all-purpose flour: The base for the dough, it creates that melt-in-your-mouth sugar cookie texture.
- 1 tsp baking powder: Helps the cookies rise slightly for a light, airy bite.
- 1 tsp cornstarch: Adds softness and a delicate texture to the cookie dough.
- ½ tsp salt: Balances sweetness and enhances other flavors in the dough.
- 13 canned pineapple slices: The star of the show, delivering juicy sweetness and vibrant color to each cookie.
- 13 maraschino cherries: Playful bursts of bright, sweet flavor and a lovely pop of red on top.
- ½ cup butter, melted: Mixed with brown sugar to create the luscious caramel base that coats the pan.
- 1 cup light brown sugar, packed: Adds that deep, caramel flavor essential for authentic pineapple upside down goodness.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Prepare the Caramel Base
Start by mixing your melted butter and packed light brown sugar until well combined, creating a smooth caramel-like mixture. Spoon about one tablespoon of this down into the bottom of each cavity of your prepared cookie pan, then spread it to cover the surface evenly. This step is what gives the cookies that signature caramelized sweetness you dream about.
Step 2: Add the Pineapple and Cherry
Next, place one canned pineapple slice on top of the brown sugar mixture in each cavity. Center a maraschino cherry right in the middle of the pineapple slice to add a gorgeous pop of color and a sweet bite. These fruit toppings will caramelize beautifully while baking, giving those classic upside down flavors in every cookie.
Step 3: Mix the Cookie Dough
In a large mixing bowl, cream together the room temperature butter and granulated sugar until fluffy and light. Beat in the eggs one at a time, then blend in the vanilla extract and sour cream for that luscious tang. In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet mixture, stirring just until combined. The dough should be soft but firm enough to shape.
Step 4: Assemble and Bake
Drop or gently press enough cookie dough over each pineapple and cherry layer to cover the top completely, smoothing it out as best you can. Bake the cookies at 350°F (175°C) for about 20 to 25 minutes, or until the edges are lightly golden and a toothpick inserted in the center comes out clean. Once done, allow the cookies to cool in the pan for about 10 minutes before carefully inverting them onto a wire rack to cool completely. This flipping step reveals the beautifully caramelized pineapple topping and gives these cookies their signature look.
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
For an extra touch of elegance, try sprinkling a light dusting of powdered sugar over the cooled cookies. A small dollop of whipped cream or a drizzle of caramel sauce can make these cookies feel even more indulgent. If you want to get creative with texture, a sprinkle of toasted coconut flakes on top adds a subtle crunch and tropical vibe that pairs wonderfully with the pineapple.
Side Dishes
If you’re serving these cookies at a party or gathering, pair them with a scoop of vanilla ice cream or a glass of cold milk to balance the sugary richness. Fresh fruit salad on the side can complement the pineapple beautifully and bring a refreshing contrast. For an adult twist, a cup of spiced chai or a tropical cocktail would elevate the entire experience.
Creative Ways to Present
Want to wow your guests? Arrange the Pineapple Upside Down Sugar Cookies Recipe on a beautiful platter lined with fresh pineapple leaves or edible flowers for natural charm. Serving them alongside mini jars of caramel sauce lets everyone add an extra drizzle to their liking. For a fun presentation, place the cookies in small cupcake liners to keep each portion neat and easy to handle.
Make Ahead and Storage
Storing Leftovers
These cookies keep fantastically well if stored in an airtight container at room temperature for up to 4 days. This helps them maintain their soft texture and ensures the pineapple topping stays juicy but not soggy. If humidity is high, a cool, dry place like the pantry is best to avoid any moisture buildup.
Freezing
To keep the magic of this Pineapple Upside Down Sugar Cookies Recipe intact for longer, you can freeze the baked cookies. Place them in a single layer on a baking sheet and freeze until solid, then transfer to a freezer-safe container or bag. They’ll stay fresh for up to 3 months. When you’re ready to enjoy, thaw them overnight in the refrigerator.
Reheating
If you prefer warm cookies, pop thawed Pineapple Upside Down Sugar Cookies in an oven preheated to 300°F (150°C) for about 5 minutes. This brings back that freshly-baked softness and slightly gooey topping, making every bite feel like it just came out of the oven.
FAQs
Can I use fresh pineapple instead of canned for this recipe?
While canned pineapple slices work best for consistent size and moisture, you can certainly try fresh pineapple. Just slice it evenly and consider lightly cooking or macerating it first to ensure it caramelizes nicely in the cookie pan.
What if I don’t have a cookie pan with cavities?
If you don’t have a muffin tin or similar pan, a small cupcake pan works perfectly. The key is to create individual portions so each cookie has that beautiful pineapple upside down presentation.
Can I make these cookies vegan or dairy-free?
You can substitute the butter with a plant-based alternative and use an egg replacer like flax eggs. For sour cream, a coconut yogurt or dairy-free sour cream alternative can work well. Just be mindful that texture might shift slightly.
How do I prevent the cookies from sticking when I invert them?
Melted butter and brown sugar create a natural non-stick caramel layer, but to be safe, grease your pan thoroughly before assembling. Allow the cookies to cool slightly before flipping, and use a thin spatula to gently help loosen the edges.
What’s the best way to achieve a soft cookie texture?
The combination of sour cream and cornstarch in the dough is essential for softness. Be careful not to overbake, and try to remove the cookies from the oven as soon as they are lightly golden and set in the center for maximum tender chewiness.
Final Thoughts
There is something truly heartwarming about this Pineapple Upside Down Sugar Cookies Recipe. It’s a charming spin on a beloved classic that’s bursting with caramelized fruit flavor and soft, buttery cookie dough. Whether you bake it for a casual treat or a special occasion, it’s the kind of recipe that brings smiles and happy memories every time. I can’t wait for you to try it and make it your own sweet tradition!
Print
Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 20 minutes
- Cook Time: 25 minutes
- Total Time: 45 minutes
- Yield: 13 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
This Pineapple Upside Down Sugar Cookies recipe combines the classic flavors of pineapple upside down cake with the delightful texture of sugar cookies. With a buttery, soft cookie base topped with caramelized brown sugar, pineapple slices, and maraschino cherries, these cookies are a perfect treat for any occasion.
Ingredients
Cookie Dough
- 1 cup butter, room temperature
- 1 ½ cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- ½ tsp salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Prepare the Brown Sugar Mixture: In a small bowl, mix melted butter and packed light brown sugar until well combined. This mixture will caramelize under the pineapple to create the classic upside-down topping effect.
- Line the Pan: Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of a muffin or cupcake pan. Spread it evenly to cover the bottom completely.
- Add Pineapple and Cherry: Place one canned pineapple slice on top of the brown sugar mixture in each cavity. Center a maraschino cherry in the middle of each pineapple slice to add color and flavor.
- Make the Cookie Dough: In a large mixing bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Beat in eggs one at a time, then mix in vanilla extract and sour cream until smooth.
- Combine Dry Ingredients: In a separate bowl, sift together all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined to form a soft dough.
- Fill the Muffin Cups: Divide the cookie dough evenly and gently drop it over the pineapple and cherry topping in each muffin cavity, filling them about 2/3 full. Smooth the tops lightly for even baking.
- Bake the Cookies: Preheat your oven to 350°F (175°C). Bake the cookies for 20-25 minutes, or until the edges are golden and a toothpick inserted into the center comes out clean.
- Cool and Invert: After baking, allow the cookies to cool in the pan for about 5 minutes. Carefully run a knife around the edges and invert each cookie onto a cooling rack or serving plate so the pineapple and cherry side is facing up.
- Serve: Let the cookies cool completely before serving to allow the caramelized topping to set. Enjoy these pineapple upside down sugar cookies fresh or store in an airtight container for up to 3 days.
Notes
- Using canned pineapple slices makes it easier to handle and ensures consistent sweetness.
- Be careful when inverting the cookies as the topping can be sticky and delicate.
- These cookies are best enjoyed within a few days for optimal freshness.
- Substitute vegan butter and egg replacers to make this recipe vegan-friendly.
