Amazing Pineapple Upside-Down Sugar Cookies for Desserts

Pineapple Upside Sugar Cookies – just hearing those words might conjure images of sunshine, sweetness, and a delightful twist on two beloved classics. Imagine all the sun-drenched, caramelized goodness of a classic pineapple upside-down cake, perfectly shrunk into a delightful, hand-held sugar cookie. This ingenious fusion takes everything you adore about the iconic dessert and makes it incredibly approachable, bringing a burst of tropical joy to your kitchen.

The pineapple upside-down cake itself boasts a charming history, rising to immense popularity in American kitchens during the early to mid-20th century. It quickly became a symbol of retro elegance and a testament to the fruit’s sweet appeal, often appearing at potlucks and family gatherings. We’re paying homage to that beloved dessert, transforming its essence into a smaller, equally irresistible format that’s perfect for sharing and easy to enjoy.

People adore this dish not just for its stunning presentation, with that glistening pineapple ring taking center stage, but for the incredible symphony of flavors and textures. The buttery, tender sugar cookie provides the perfect canvas for the juicy, slightly tart pineapple, all brought together by a golden, caramelized brown sugar topping. It’s a nostalgic trip with a modern twist, offering all the joy of a cake in a convenient, shareable package. These Pineapple Upside Sugar Cookies are simply irresistible and a fantastic way to elevate your baking, promising to be a showstopper at any gathering or a delightful treat for yourself.

Ingredients:

• For the Pineapple Topping:
• 4 tablespoons (56g) unsalted butter, melted
• ½ cup (100g) packed light brown sugar
• 1 (8-ounce) can crushed pineapple, well-drained (or about 10-12 pineapple rings/slices from a 20-ounce can, patted very dry and chopped finely)
• 12-18 maraschino cherries, halved or whole, stems removed and patted dry
• For the Sugar Cookies:
• 2 ½ cups (300g) all-purpose flour, plus more for dusting
• 1 teaspoon baking powder
• ½ teaspoon salt
• 1 cup (226g) unsalted butter, softened to room temperature
• 1 ½ cups (300g) granulated sugar
• 2 large eggs, at room temperature
• 1 teaspoon vanilla extract
• ½ teaspoon almond extract (optional, but highly recommended for depth)
• For the Optional Pineapple Glaze:
• 1 cup (120g) powdered sugar, sifted
• 2-3 tablespoons reserved pineapple juice (from the crushed pineapple or canned rings)
• ½ teaspoon vanilla extract

Preparing the Pineapple Topping

1. First things first, let’s get that gorgeous pineapple topping ready, as it truly makes these Pineapple Upside Sugar Cookies so special and unique! You’ll want to preheat your oven to 375°F (190°C). This ensures that once our cookies are assembled, they can go straight into a hot oven, promoting even baking and that beautiful caramelized crust.
2. Next, grab a standard 12-cup muffin tin. This recipe is designed to create individual cookie delights, so a muffin tin is absolutely essential for shaping our cookies and holding the topping in place. I like to lightly grease each muffin cup, even if it’s non-stick, just for extra insurance against sticking. A quick spray with non-stick cooking spray works wonders.
3. In a small microwave-safe bowl or saucepan, melt your 4 tablespoons of unsalted butter. You want it fully liquid, but not boiling hot. Once melted, carefully divide the butter among the 12 muffin cups. I usually pour about ½ teaspoon into the bottom of each cup, ensuring an even distribution for that rich, buttery foundation.
4. Now, for the brown sugar layer. Sprinkle approximately 1 to 1 ½ tablespoons of packed light brown sugar evenly over the melted butter in each muffin cup. Don’t be shy here; this sugar will caramelize beautifully with the butter and pineapple during baking, creating the signature “upside-down” effect. Gently press the sugar down a bit with the back of a spoon to ensure it forms a relatively flat base. This step is critical for developing that deep, molasses-rich flavor that pairs so wonderfully with pineapple.
5. For the pineapple itself, if you’re using crushed pineapple from a can, it’s absolutely vital that you drain it exceptionally well. Excess moisture will lead to soggy cookies, which we definitely don’t want. I usually press it through a fine-mesh sieve or even pat it dry with paper towels to remove as much liquid as possible. If you’re using pineapple rings or slices, make sure to pat them very dry and then chop them into small, manageable pieces – about ¼-inch dice is perfect. Divide the drained or chopped pineapple among the 12 muffin cups, placing it directly on top of the brown sugar layer. You want a nice, even layer, but avoid overfilling.
6. Finally, the iconic maraschino cherry! Take your halved (or whole, if you prefer) maraschino cherries, making sure they’re also patted dry to remove any excess syrup. Place one or two cherry halves, cut-side down, into the center of the pineapple layer in each muffin cup. The vibrant red against the golden pineapple really pops and gives these Pineapple Upside Sugar Cookies their classic look. Set your prepared muffin tin aside while we work on the cookie dough. This gives the butter and sugar a moment to meld slightly.

Making the Sugar Cookie Dough

1. Let’s get started on the cookie dough, the tender base for our delightful Pineapple Upside Sugar Cookies! In a medium bowl, whisk together your dry ingredients: the all-purpose flour, baking powder, and salt. Make sure to whisk them thoroughly for about 30 seconds to a minute. This ensures that the leavening agent (baking powder) and salt are evenly distributed throughout the flour, which is crucial for uniform texture and flavor in every cookie. Set this dry mixture aside for now.
2. Now, in the large bowl of a stand mixer fitted with the paddle attachment, or with a hand mixer and a large mixing bowl, we’re going to cream together the softened unsalted butter and granulated sugar. I cannot stress enough the importance of truly room temperature butter here. It should be soft enough to leave an indentation when gently pressed, but not at all melted or greasy. This allows it to properly aerate with the sugar. Begin mixing on low speed until the sugar is just incorporated, then increase the speed to medium-high. Beat this mixture for a good 3-5 minutes, periodically scraping down the sides of the bowl with a rubber spatula. You’re looking for a mixture that is light in color, pale yellow, and wonderfully fluffy. This creaming process incorporates air, which is the secret to a tender, not dense, sugar cookie.
3. Once your butter and sugar mixture is light and fluffy, it’s time to add the eggs. Add them one at a time, beating well after each addition. After the first egg goes in, beat until it’s fully incorporated into the mixture before adding the second. This prevents the mixture from curdling and ensures a smooth emulsion. Scrape down the sides of the bowl again after both eggs are incorporated to make sure everything is well combined.
4. Next, stir in your vanilla extract and, if you’re using it, the almond extract. I personally find that a touch of almond extract elevates the flavor profile of sugar cookies beautifully, adding a subtle complexity that complements the pineapple without overpowering it. Beat these extracts in until they are just combined. You’ll notice a lovely aroma already starting to fill your kitchen!
5. With the wet ingredients perfectly mixed, it’s time to gradually add the dry ingredients to the wet. With the mixer on low speed, slowly add the flour mixture, about one-third at a time, to the butter mixture. Mix only until the flour is just incorporated, being very careful not to overmix. Overmixing develops the gluten in the flour, which can lead to tough, chewy cookies – and we’re aiming for perfectly tender Pineapple Upside Sugar Cookies! As soon as you see no streaks of dry flour, stop the mixer. A quick final scrape with your rubber spatula will ensure everything is homogeneous.
6. At this point, your cookie dough will be relatively soft, but manageable. While some sugar cookie recipes call for chilling, we want this dough to be pliable enough to easily press into our muffin tins. However, if your kitchen is particularly warm or your dough seems excessively sticky, a quick 15-20 minute chill in the refrigerator can make it easier to handle. Just keep an eye on it to ensure it doesn’t become too firm.

Assembling and Baking the Pineapple Upside Sugar Cookies

1. Now for the fun part – assembling our beautiful Pineapple Upside Sugar Cookies! Remember that muffin tin we prepared earlier with the butter, brown sugar, pineapple, and cherries? Grab it from where you set it aside.
2. Using a standard cookie scoop (about 1.5 to 2 tablespoons) or simply a spoon, scoop portions of your sugar cookie dough. You’ll want about 2 to 2 ½ tablespoons of dough for each muffin cup. Gently place each scoop of dough directly on top of the pineapple and cherry layer in each prepared muffin cup.
3. Once the dough is in place, you’ll need to gently press it down and out to completely cover the pineapple and cherry layer, extending to the edges of the muffin cup. Use your fingers, lightly floured if the dough is sticky, or the back of a small spoon. The goal is to create a flat, even layer of cookie dough over the topping. This ensures that when the cookies are flipped, the topping is beautifully encapsulated and creates that stunning “upside-down” effect. Try not to press too hard, as you don’t want to disturb the carefully arranged topping beneath, but make sure it’s a full seal.
4. With all 12 cups filled and smoothed, carefully transfer the muffin tin to your preheated 375°F (190°C) oven. We’re going to bake these delightful treats for approximately 12-15 minutes. Baking times can vary depending on your oven, so it’s always a good idea to keep a close eye on them, especially during the first batch.
5. What to look for during baking: The cookies are done when the edges are lightly golden brown and the centers are set. They shouldn’t look wet or overly pale in the middle. The aroma of baking sugar cookies combined with warm caramelized pineapple will be absolutely divine and will fill your kitchen, making it hard to wait! If you see any bubbling around the edges from the butter and sugar, that’s a good sign the caramelization is happening.
6. Once baked, carefully remove the muffin tin from the oven. This is a crucial step for preventing sticking and ensuring a clean release. Immediately, while the cookies are still very warm in the tin, place a wire cooling rack on top of the muffin tin. With oven mitts protecting your hands, firmly hold the cooling rack and the muffin tin together, and swiftly but carefully invert the entire assembly. The cookies should release cleanly onto the wire rack, landing with their beautiful pineapple topping facing upwards. If a cookie seems stuck, gently tap the bottom of the muffin tin, or carefully use a small offset spatula around the edges of any stubborn cookie to help it release.
7. Allow the Pineapple Upside Sugar Cookies to cool on the wire rack for at least 15-20 minutes. It’s incredibly tempting to dig in right away, but allowing them to cool slightly helps the topping set and firm up, preventing it from being too gooey and messy to handle. Plus, the flavors will develop even further as they cool.

Finishing Touches: The Optional Pineapple Glaze

1. While your delicious Pineapple Upside Sugar Cookies are cooling, you can whip up a quick and easy pineapple glaze to add an extra layer of sweetness and shine. This step is entirely optional, as the cookies are absolutely fantastic on their own, but it does add a lovely touch and enhances the pineapple flavor even more.
2. In a small bowl, combine your sifted powdered sugar. Sifting is important here to prevent lumps and ensure a silky-smooth glaze.
3. Gradually add the reserved pineapple juice, starting with 2 tablespoons. You want to add just enough to achieve a smooth, pourable consistency that is thick enough to coat a spoon but still flows easily. Whisk vigorously until the glaze is completely smooth and lump-free. If it’s too thick, add a tiny bit more pineapple juice (or even a drop of milk or water) until it reaches your desired consistency. If it’s too thin, you can whisk in a little more powdered sugar.
4. Finally, stir in your ½ teaspoon of vanilla extract. This complements the existing flavors beautifully.
5. Once your cookies have cooled sufficiently, you can drizzle the glaze over the tops of each cookie using a spoon, or you can even dip the tops of the cookies into the glaze for a more uniform coating. Let the glaze set for a few minutes before serving. This truly finishes off these incredible Pineapple Upside Sugar Cookies, making them not only a treat for the taste buds but also a feast for the eyes! Enjoy these wonderfully unique and utterly delicious cookies!

Conclusion:

Well, my friends, we’ve reached the sweet end of our journey, and I genuinely hope you’re feeling as inspired as I am about these incredible cookies. If there’s one recipe you absolutely must add to your baking repertoire this year, it’s this one. These aren’t just any cookies; they are a delightful escape, a burst of sunshine in every bite, and truly a testament to how simple ingredients can create something profoundly special. The rich, buttery base, the tender chewiness, and that vibrant, caramelized pineapple ring topped with a jewel-like cherry all come together in a symphony of flavors and textures that is utterly irresistible. I promise you, the moment you pull these golden beauties from your oven, the aroma alone will have you completely captivated.

What truly makes these Pineapple Upside Sugar Cookies stand out from the crowd is their unique charm and surprisingly straightforward preparation. You might expect something this elegant and flavorful to require intricate steps, but the beauty lies in its simplicity. They offer that perfect balance of comfort food nostalgia with a gourmet twist. Each cookie is a miniature work of art, individually portioned, making them ideal for sharing or savoring solo. They’re a conversation starter, a mood lifter, and an instant classic that brings a genuine smile to anyone who tries them. You’re not just baking a cookie; you’re crafting a little moment of joy, a tiny edible celebration of tropical bliss and home-baked goodness.

Now, let’s talk about enjoying these delightful treats. While they are undeniably perfect on their own, perhaps with a quiet cup of coffee or a soothing herbal tea, don’t hesitate to get creative with your serving! Imagine pairing one of these warm, tender cookies with a scoop of creamy vanilla bean ice cream, allowing the cool, melting richness to complement the warm, fruity cookie. Or, for an extra touch of tropical flair, a scoop of coconut sorbet would be absolutely divine. They also make a stunning addition to any dessert platter, adding a pop of color and a unique flavor profile that sets them apart from typical offerings. And if you’re looking for a heartfelt, homemade gift, these cookies are absolutely perfect – package a few in a pretty box, and you’ve got a present that speaks volumes about your care and culinary prowess.

Beyond serving suggestions, these cookies offer a fantastic canvas for playful variations. While the classic pineapple and cherry are iconic, feel free to experiment! A tiny sprinkle of toasted coconut flakes over the caramel before baking can add an extra layer of texture and flavor, enhancing the tropical theme. For a slightly different spice note, a hint of cardamom or a whisper of fresh ginger in the cookie dough could introduce an intriguing warmth. You could also try a different fruit if you’re feeling adventurous – perhaps a thinly sliced mandarin orange or even a delicate peach slice, though you’d want to adjust baking times slightly. For an even more indulgent finish, a delicate drizzle of white chocolate or a rum-infused glaze over the cooled cookies would elevate them further, adding another layer of sweetness and sophistication.

So, please, take this as your official invitation from me to dive into your kitchen and give these fantastic cookies a try. I promise you won’t regret it. The satisfaction of creating something so beautiful and delicious from scratch is truly one of life’s simple pleasures. I am genuinely so excited for you to experience the magic of these cookies firsthand. Once you’ve baked them and, more importantly, tasted them, I would absolutely love to hear all about it! Don’t hesitate to share your experiences, your serving ideas, or any creative variations you come up with in the comments. Your insights and culinary adventures inspire me, and I’m always thrilled to connect with fellow food lovers. Happy baking, and enjoy every single delicious bite!