Pineapple Upside Down Sugar Cookies

Picture this: the sweet caramelized aroma of brown sugar and butter, the tangy brightness of pineapple, and the melt-in-your-mouth texture of a soft sugar cookie. These Pineapple Upside Down Sugar Cookies transform the beloved classic cake into a handheld treat that’s both nostalgic and innovative. The contrast between the gooey caramelized pineapple topping and the tender cookie base creates an irresistible dessert that’s perfect for any occasion. You’ll learn how to create these show-stopping cookies with simple ingredients and foolproof techniques that guarantee perfect results every time.

Why You’ll Love This Recipe

These Pineapple Upside Down Sugar Cookies deliver all the flavor of the traditional cake in a convenient, portable form that’s perfect for sharing. The buttery cookie base provides the perfect canvas for the caramelized brown sugar and pineapple topping, creating a delightful contrast between soft and chewy textures. Each bite offers the perfect balance of sweetness from the sugar cookie and tanginess from the pineapple.

What makes these cookies truly special is how they capture the essence of pineapple upside down cake without the fuss. They come together in less than an hour, making them ideal for last-minute gatherings or when you need to satisfy a sweet craving quickly. The dramatic reveal as you flip each cookie is just as satisfying as turning out a full-sized cake, but with individual portions that are perfect for serving.

Best of all, these upside down pineapple cookies are versatile enough for any occasion—from casual family desserts to elegant dinner parties where you want to impress with something unique but familiar.

Ingredients

For the Caramelized Pineapple Topping:

• 4 tablespoons (56g) unsalted butter
• 3/4 cup (150g) brown sugar, packed
• 1 can (20 oz/567g) pineapple rings, drained (reserve 2 tablespoons juice)
• 12-15 maraschino cherries, halved

For the Sugar Cookie Base:

• 2 1/2 cups (315g) all-purpose flour
• 1/2 teaspoon baking powder
• 1/2 teaspoon salt
• 3/4 cup (170g) unsalted butter, softened
• 1 cup (200g) granulated sugar
• 1 large egg, room temperature
• 1 teaspoon vanilla extract
• 2 tablespoons reserved pineapple juice
• 1/4 teaspoon almond extract (optional, enhances flavor)

Pro Tips

Perfect Caramelization: The key to exceptional Pineapple Upside Down Sugar Cookies lies in properly caramelizing the brown sugar and butter mixture. Cook it just until it begins to bubble around the edges but not so long that it burns. This typically takes 3-4 minutes on medium heat. This creates that signature amber-colored, slightly chewy topping that makes these cookies irresistible.

Cookie Dough Consistency: For the ideal texture, your cookie dough should be soft but not sticky. If it’s too sticky to handle, refrigerate for 15-20 minutes before shaping. However, don’t chill it for too long, as cold dough won’t mold properly around the pineapple. The dough should feel like play-dough when ready.

The Flip Technique: The most crucial moment comes when flipping these cookies. Allow them to cool in the pan for exactly 5 minutes after baking – any sooner and they’ll fall apart, any later and the caramel might harden too much, making removal difficult. Place your cooling rack over the pan, hold them firmly together with oven mitts, and flip in one confident motion to prevent any topping from sticking to the pan.

Instructions

Step 1: Prepare Your Baking Sheets
Preheat your oven to 350°F (175°C). Line two muffin tins or baking sheets with parchment paper if using regular cookie sheets. If using muffin tins, lightly grease each cup with cooking spray. The individual wells of a muffin tin help contain the caramel topping beautifully, but regular baking sheets work well too.

Step 2: Create the Caramel Base
In a small saucepan, melt butter over medium heat. Add brown sugar and stir constantly until the mixture becomes smooth and begins to bubble slightly, about 3 minutes. Remove from heat and let cool for 5 minutes. If using muffin tins, spoon about 1 tablespoon of the mixture into each cup. If using baking sheets, drop tablespoon-sized portions about 3 inches apart.

Step 3: Add Pineapple and Cherries
Cut pineapple rings into quarters (or smaller if needed). Place one piece of pineapple onto each caramel portion, pressing gently. Add half a maraschino cherry beside each pineapple piece, pressing slightly into the caramel. The arrangement might seem small, but remember the cookie dough will spread around it.

Step 4: Prepare the Cookie Dough
In a medium bowl, whisk together flour, baking powder, and salt. In a separate large bowl, beat softened butter and granulated sugar until light and fluffy, about 3 minutes. Add egg, vanilla extract, pineapple juice, and almond extract if using. Mix until well combined. Gradually add the dry ingredients to the wet ingredients, mixing just until incorporated.

Step 5: Form and Bake the Cookies
Using a cookie scoop or spoon, drop about 2 tablespoons of dough over each pineapple-topped caramel portion. Gently press the dough to flatten slightly, but don’t press all the way to the edges—the dough will spread during baking. Bake for 12-15 minutes until the cookies are just turning golden at the edges but still soft in the center.

Step 6: The Dramatic Flip
Allow cookies to cool in the pan for exactly 5 minutes. Run a knife around the edge of each cookie to loosen. Place a cooling rack or serving plate over the pan and, using oven mitts, carefully flip the entire pan in one swift motion. Leave the pan in place for 30 seconds to allow the caramel to drip down onto the cookies, then gently lift it off. Let the Pineapple Upside Down Sugar Cookies cool completely before serving.

Variations

Tropical Twist: Transform your Pineapple Upside Down Sugar Cookies into a truly tropical treat by adding 1/2 cup toasted coconut flakes to the cookie dough and substituting coconut extract for the almond extract. This variation adds a delightful texture contrast and enhances the island-inspired flavors. For an extra touch, sprinkle additional toasted coconut around the edges after flipping.

Mini Cookie Cups: Create bite-sized treats by using mini muffin tins instead of regular-sized ones. Cut the pineapple into smaller pieces and use tiny pieces of cherries. Reduce the baking time to 8-10 minutes. These adorable mini upside down pineapple cookies are perfect for parties and dessert trays where guests can sample multiple desserts.

Gluten-Free Option: For those with gluten sensitivities, substitute the all-purpose flour with a high-quality gluten-free flour blend that contains xanthan gum. Add an additional egg yolk to the cookie dough to help with binding and texture. The result is a tender cookie that everyone can enjoy without sacrificing the classic flavor profile.

Storage and Serving

These Pineapple Upside Down Sugar Cookies are best enjoyed the day they’re made when the caramel topping is still slightly warm and gooey. Store any leftovers in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 5 days. To reheat, microwave individual cookies for 10-15 seconds to restore that fresh-baked texture and slightly warm the caramel topping.

For serving, these cookies make a stunning presentation on their own, but you can elevate them further by pairing with complementary elements. Serve alongside a scoop of vanilla bean ice cream for a delightful temperature contrast—the warm cookie with cold ice cream creates an irresistible dessert experience. For a more elegant presentation, drizzle with a light rum sauce and garnish with fresh mint leaves.

These cookies also make excellent gifts! Stack them in decorative tins with parchment paper between layers to prevent sticking, and they’ll bring joy to anyone lucky enough to receive them.

FAQs

Can I use fresh pineapple instead of canned?
Yes, but you’ll need to prepare it properly. Fresh pineapple should be cut into 1/4-inch thick slices and patted very dry with paper towels to remove excess moisture. You’ll also need to create your own pineapple juice for the dough by blending a small piece of pineapple and straining it.

Why did my caramel harden too quickly?
This typically happens when the caramel cools too much before adding the cookie dough. Work quickly after preparing the caramel, and if it begins to harden, gently rewarm it on low heat until it’s pliable again before proceeding.

Can I make the dough ahead of time?
Yes, the cookie dough can be prepared up to 24 hours in advance and refrigerated. However, let it come to room temperature for about 30 minutes before using, as it needs to be soft enough to shape around the pineapple.

My cookies stuck to the pan when flipping. How can I prevent this?
Make sure to run a knife around each cookie before flipping, and don’t let them cool for more than 5 minutes in the pan. Using parchment paper or silicone muffin liners can also help prevent sticking.

Can I freeze these cookies?
Yes, though the texture of the pineapple may change slightly upon thawing. Freeze in a single layer until solid, then transfer to an airtight container with parchment between layers. Thaw at room temperature and warm slightly before serving for best results.

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