If you have a soft spot for classic desserts with a tropical twist, you’re going to adore this Pineapple Upside Down Sugar Cookies Recipe. Imagine the buttery, tender crumb of a sugar cookie combined with the caramelized sweetness of pineapple and brown sugar just like the cake, but in a fun, handheld treat. The pineapple slices and maraschino cherries create a vibrant, joyful look while the rich brown sugar topping melts into the cookie base, giving each bite a magical burst of flavor. It’s the perfect way to bring a little sunshine to your baking, and oh, how irresistible these cookies are when fresh from the oven!
Ingredients You’ll Need
Each ingredient in this recipe plays a crucial role, from creating the perfect cookie texture to delivering that signature pineapple upside down flavor. Keeping it simple is the key here, so you’ll be thrilled at how pantry staples come together to make something extraordinary.
- 1 cup butter, room temperature: This adds richness and helps create a soft, tender crumb in the cookies.
- 1 ½ cups granulated sugar: Sweetens the dough and helps it brown beautifully when baked.
- 2 eggs: Bind all ingredients together and give structure to the cookies.
- 2 tsp vanilla extract: Adds warmth and depth of flavor, complementing the pineapple perfectly.
- ½ cup sour cream: Keeps the cookies moist and adds a subtle tang that brightens the overall flavor.
- 3 cups all-purpose flour: The base of the dough, giving it body and that classic cookie texture.
- 1 tsp baking powder: Helps the cookies rise slightly, making them light and fluffy.
- 1 tsp cornstarch: Adds tenderness by softening the flour’s gluten network.
- ½ tsp salt: Balances sweetness and enhances all the other flavors.
- 13 canned pineapple slices: The star of the show, bringing juicy sweetness and a tropical flair.
- 13 maraschino cherries: For that classic pop of vibrant color and a little extra sweetness on top.
- ½ cup butter, melted: Mixed with brown sugar, this creates the luscious caramel topping layer.
- 1 cup light brown sugar, packed: Gives the cookies their signature rich, molasses-like flavor in the topping.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Prepare Your Pan and Topping
Start by getting your muffin or cookie pan ready. Spoon about one tablespoon of the melted butter and brown sugar mixture into the bottom of each cavity, spreading it evenly so the entire base gets caramelized. This step is what creates that signature sticky-sweet bottom, so don’t rush it!
Step 2: Arrange Pineapple and Cherry
Next, place a pineapple slice on top of the brown sugar layer in each cavity, carefully centering one maraschino cherry right in the middle of each pineapple ring. This not only looks fantastic but ensures every cookie gets a burst of fruity sweetness with every bite.
Step 3: Make the Cookie Dough
In a large bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Add the eggs and vanilla extract, mixing well after each addition to incorporate air and build the perfect crumb texture. Then, mix in the sour cream for moisture and tang.
Step 4: Combine Dry Ingredients
Whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add this dry mixture to the wet ingredients, stirring until you have a smooth dough. Be careful not to overmix—just combine until everything is evenly incorporated.
Step 5: Assemble and Bake
Drop spoonfuls of dough over the pineapple and cherry topping in each pan cavity, filling each about two-thirds full to allow room for rising. Bake in a preheated oven until the cookies turn golden and a toothpick inserted in the center comes out clean, around 18 to 20 minutes. Once baked, let them cool for a few minutes in the pan before carefully flipping them upside down onto a cooling rack to reveal the gorgeous pineapple tops.
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
These cookies are stunning all on their own, but a light dusting of powdered sugar right before serving adds a delicate sweetness and a pretty finishing touch. For extra flair, you can also drizzle some warm caramel sauce over the top or add a small sprig of fresh mint for a pop of color and freshness.
Side Dishes
Pineapple Upside Down Sugar Cookies are perfect as a sweet treat alongside a fruity iced tea or a creamy vanilla milkshake. If you’re serving these at a brunch or party, a bowl of fresh berries or a tropical fruit salad pairs wonderfully, enhancing the sunny, pineapple theme.
Creative Ways to Present
Try serving these cookies on a platter lined with fresh pineapple leaves or banana leaves for a festive tropical vibe. You can also place each cookie in a colorful cupcake liner for easy serving at gatherings. For a fun twist, stack them slightly warm with a scoop of vanilla ice cream in between for an irresistible dessert sandwich.
Make Ahead and Storage
Storing Leftovers
The cookies will keep well in an airtight container at room temperature for up to three days. The topping may soften slightly, but the flavors will continue to meld beautifully. Just make sure to store them in a single layer or separated by parchment paper to avoid sticking.
Freezing
If you want to keep these treats longer, they freeze wonderfully. Place the cooled cookies in a freezer-safe container or bag, with parchment paper between layers to prevent them from clumping together. Freeze for up to two months. When you’re ready to enjoy, thaw at room temperature.
Reheating
For that freshly baked feel, pop frozen or refrigerated cookies into a 300°F oven for about 5 to 7 minutes. This will warm the pineapple topping and soften the cookie, delivering that satisfying texture and flavor just like fresh out of the oven.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple slices work wonderfully and can add an extra juicy brightness. Just be sure to drain any excess juice so the cookies don’t become too soggy.
What if I don’t have cornstarch?
You can skip the cornstarch or substitute it with an equal amount of arrowroot powder. It helps keep the cookies tender, but leaving it out won’t ruin the recipe.
Do the cookies need to be flipped to serve?
Yes, flipping the pan after baking showcases the beautiful caramelized pineapple and cherry on top. It’s the signature look that makes this Pineapple Upside Down Sugar Cookies Recipe so special.
Can I use a different type of cherry?
Maraschino cherries are traditional because of their sweetness and color, but you can try glacé cherries or even fresh cherries if they’re in season. Just keep in mind it might slightly change the taste and appearance.
Are these cookies gluten-free?
Not as written, since they use all-purpose flour. However, you can experiment with gluten-free flour blends that substitute cup for cup to make them suitable for gluten-intolerant diets.
Final Thoughts
Now that you’ve got the full scoop on the Pineapple Upside Down Sugar Cookies Recipe, it’s time to bake up a batch and share the joy with your loved ones. These cookies bring that perfect balance of tropical sweetness and classic cookie goodness that everyone will want seconds of. Baking them is a little celebration of sunshine and sweetness, and trust me—you’ll find yourself coming back to this recipe again and again.
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
These Pineapple Upside Down Sugar Cookies combine the classic tropical flavor of pineapple upside down cake with the delightful texture of sugar cookies. Each cookie features a juicy pineapple slice and a maraschino cherry on top, caramelized with a brown sugar and butter base, making them irresistibly sweet and perfect for gatherings or a fun dessert treat.
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, combine the melted butter and light brown sugar until well mixed to form a consistent caramel-like base.
- Line the baking pan: Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity of your prepared cookie pan or muffin tin. Spread it evenly to cover the bottom completely.
- Add fruit toppings: Place a canned pineapple slice on top of the brown sugar mixture in each cavity, then center a maraschino cherry in the middle of each pineapple slice to decorate.
- Make the cookie dough: In a large mixing bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla extract and sour cream until combined.
- Combine dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet mixture, mixing gently until a soft dough forms.
- Assemble the cookies: Drop spoonfuls of the cookie dough over the pineapple and cherry in each cavity, covering the fruit topping but not pressing down too hard so the caramel topping remains visible.
- 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 near the cookie dough comes out clean.
- Cool and invert: Allow the cookies to cool in the pan for about 10 minutes. Carefully invert the pan onto a cooling rack or serving tray so the caramelized fruit topping is displayed on top of the cookies.
- Serve: Serve the pineapple upside down sugar cookies warm or at room temperature for the best flavor and texture experience.
Notes
- Use canned pineapple slices packed in juice, not syrup, to keep sugar levels balanced.
- Ensure the butter for the cookie dough is at room temperature for better creaming results.
- You can line the pan with parchment paper for easier removal or use silicone muffin molds.
- Store leftovers in an airtight container at room temperature for up to 3 days or refrigerate for longer freshness.
- For a more tropical twist, sprinkle a little shredded coconut on the dough before baking.
