Pineapple Upside Down Sugar Cookies

Name: Pineapple Upside Down Sugar Cookies
Prep time: 20 min
Cook time: 25 min
Total time: 45 min
Cuisine: American
Ingredients: 1 cup unsalted butter, at room temperature; 1 1/2 cups granulated sugar; 2 large eggs; 2 teaspoons vanilla extract; 1/2 cup sour cream; 3 cups all-purpose flour; 1 teaspoon baking powder; 1 teaspoon cornstarch; 1/2 teaspoon salt; 13 canned pineapple slices, drained; 13 maraschino cherries; 1/2 cup unsalted butter, melted; 1 cup light brown sugar, packed

Author: Amelia Sinclair

Published: January 15, 2026

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Introduction to Pineapple Upside Down Sugar Cookies

There’s something magical about baking a batch of cookies that brings everyone together, isn’t there? Today, I’m excited to share my recipe for Pineapple Upside Down Sugar Cookies. These enchanting treats blend the luscious flavors of pineapple upside down cake with a chewy sugar cookie base. They’re perfect for busy days when you need a quick solution to satisfy your craving or impress your loved ones with a delightful twist on a classic favorite. Trust me, once you make these, they’ll become a go-to in your cookie repertoire!

Why You’ll Love This Pineapple Upside Down Sugar Cookies

These Pineapple Upside Down Sugar Cookies are not just easy to whip up—they’re a joyful experience from start to finish. The chewy, buttery goodness complements the sweet fruitiness of pineapple, creating a flavor explosion in your mouth. Plus, they bake in just 25 minutes, making them perfect for those busy weeknights. Whether you’re indulging solo or sharing with the family, these cookies will surely brighten your day!

Ingredients for Pineapple Upside Down Sugar Cookies

When it comes to crafting the delightful Pineapple Upside Down Sugar Cookies, the ingredients are key! Here’s a quick look at what you’ll need for these scrumptious bites:

Unsalted Butter: The foundation of your cookies, giving them a rich flavor and chewy texture. Always use room temperature butter for easy mixing.
Granulated Sugar: This sweetens the cookie and helps achieve that lovely light texture. Perfect for balancing the tangy pineapple!
Eggs: A binding agent that adds moisture and richness to the cookie dough. They help create a nice rise.
Vanilla Extract: A splash of this aromatic goodness enhances the flavor. Trust me, it makes all the difference!
Sour Cream: This adds a subtle tang and moisture, making your cookies soft and tender. It’s a secret weapon in baking!
All-Purpose Flour: The main structure of your cookies. It’s essential for that perfect chewy bite.
Baking Powder: Creates a nice lift in your cookies, helping them rise beautifully when they bake.
Cornstarch: A key player for soft texture! It keeps your cookies tender while still allowing them to hold their shape.
Salt: Just a pinch helps elevate all the other flavors, balancing out the sweetness.
Canned Pineapple Slices: These add that iconic fruity flavor and are super convenient. But if you can get fresh pineapple, it’s even better!
Maraschino Cherries: These cuties are more than just a garnish! They add a touch of sweetness and color, making your cookies truly eye-catching.
Melted Unsalted Butter: This is used to create a luscious brown sugar glaze, giving your cookies that nostalgic cake-like vibe.
Light Brown Sugar: Adds that delicious caramel flavor that pairs perfectly with the pineapple. It gives the glaze a lovely depth.

Don’t worry if you need to make substitutions or adaptations. Feel free to swap in gluten-free flour or use coconut cream instead of sour cream for a tropical twist! For exact measurements, check out the bottom of the article where you can find everything nicely consolidated for printing.

How to Make Pineapple Upside Down Sugar Cookies

Now let’s dive into the delightful world of baking these Pineapple Upside Down Sugar Cookies! Each step is simple, but they blend together to create a cookie that’s nothing short of a celebration. Are you ready to get your hands a little sticky? Let’s go!

Step 1: Preheat the Oven

Start by preheating your oven to 350°F (175°C). Preheating is crucial because it helps the cookies bake evenly. If the oven isn’t hot enough, they won’t rise properly. Think of it as warming up before a workout—essential for that perfect outcome!

Step 2: Cream the Butter and Sugar

In a large mixing bowl, cream together your room temperature unsalted butter and granulated sugar. Use an electric mixer until the mixture is light and fluffy. This step is critical because it incorporates air, which gives your cookies that wonderfully soft and chewy texture. You’ll know it’s done when the mixture looks pale and smooth.

Step 3: Incorporate Wet Ingredients

Next up, add in the eggs, vanilla extract, and sour cream. Mix until everything is fully integrated. The eggs add moisture and richness, while the sour cream keeps the cookies tender and flavorful. You’ll notice a lovely fragrance fill your kitchen as you mix—pure magic!

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Make sure to whisk well to avoid clumps. Trust me, you want a smooth cookie dough! This step creates the structure for your cookies, ensuring they hold their lovely shape.

Step 5: Mix Wet and Dry Together

Now, gradually add your dry mixture into the wet ingredients, mixing until just combined. Be careful not to over-mix! Overdoing it can lead to tough cookies instead of the chewy ones we are aiming for. Just stir until you don’t see any more flour; it’s okay if some lumps remain!

Step 6: Prepare the Brown Sugar Mixture

In another bowl, blend melted unsalted butter and light brown sugar until smooth, creating a luscious glaze. This mixture should be thick and syrupy. It’s what gives your cookies that nostalgic, cake-like flavor while creating a delectable layer of sweetness on top.

Step 7: Assemble the Cookies

Now it’s time to assemble! Spoon about a tablespoon of the brown sugar mixture into each cavity of a greased mini round cake pan or muffin tin. Then, place a pineapple slice over the glaze and position a maraschino cherry in the center of each fruit ring. This layering will create a stunning presentation once baked!

Step 8: Bake the Cookies

Using a 3-tablespoon scoop, portion the cookie dough over each fruit-topped cavity. Gently flatten the dough with an offset spatula for even baking. Bake for about 25 minutes, or until the cookies are golden around the edges. You’ll know they’re ready when the brown sugar is bubbling up the sides—now that’s a sight!

Step 9: Cool and Invert

Once baked, cool them for about 10 minutes. Then, carefully invert the cookies onto wax paper, allowing the luscious brown sugar glaze to cascade over the tops. This is where the magic happens—your kitchen should smell like a tropical paradise!

Step 10: Enjoy!

Finally, allow your cookies to cool completely before serving. Once done, share them with your family or enjoy them all by yourself—no judgment here! These cookies are a delightful treat that will surely spark joy in every bite.

Tips for Success

Use room temperature ingredients for better mixing and texture.
Don’t skip preheating the oven; it makes a big difference!
Measure flour properly to avoid dry or dense cookies.
Experiment with fresh pineapple for a brighter flavor.
Store cookies in an airtight container to keep them soft and fresh.
Consider adding a sprinkle of coconut for a tropical twist!

Equipment Needed

Mixing Bowls: A set of various sizes will do the trick.
Electric Mixer: Handheld works perfectly, but a stand mixer is a luxury.
Mini Round Cake Pan or Muffin Tin: You can use a regular baking sheet, too!
Offset Spatula: Essential for smoothing and flattening the dough.

Variations of Pineapple Upside Down Sugar Cookies

Coconut Delight: Add shredded coconut to the cookie dough for a tropical twist that pairs beautifully with the pineapple.
Chocolate Chip Twist: Mix in some semi-sweet chocolate chips to elevate the flavor profile and add a delicious contrast to the fruit.
Gluten-Free Option: Substitute all-purpose flour with a gluten-free blend to accommodate dietary preferences without sacrificing taste.
Lemon Zest: Incorporate lemon zest into the cookie dough for a bright, zesty flavor that enhances the tropical vibes.
Maraschino Cherry Variations: Try using fresh cherries for a burst of flavor or even experiment with other fruits like peaches or strawberries!

Serving Suggestions

Pair your Pineapple Upside Down Sugar Cookies with a scoop of vanilla ice cream for an indulgent treat.
Serve them alongside a tropical fruit salad for a vibrant presentation.
A refreshing glass of iced tea or pineapple juice complements these cookies beautifully.
For added flair, dust them with powdered sugar before serving!

FAQs about Pineapple Upside Down Sugar Cookies

Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple brings a vibrant flavor and can take these cookies to the next level. Just be sure to chop it into similar-sized pieces as the canned ones for an even bake.

How should I store my Pineapple Upside Down Sugar Cookies?
Store your cookies in an airtight container at room temperature. This will help keep them soft and fresh for up to a week. If they last that long!

Can I freeze these cookies?
Yes, you can freeze Pineapple Upside Down Sugar Cookies! Just allow them to cool completely, then place them in a freezer-safe container. They’ll be good for about three months. When you’re ready to enjoy, just thaw them at room temperature.

What can I substitute for sour cream?
If you don’t have sour cream on hand, you can use plain yogurt or even buttermilk. Both will keep the cookies moist and tender!

How do I know when the cookies are done baking?
Look for a golden edge and watch for bubbling brown sugar. If your cookies are rising nicely and don’t jiggle when you gently tap the pan, they’re probably done!

Final Thoughts

Baking Pineapple Upside Down Sugar Cookies isn’t just about making a treat; it’s about creating memories with loved ones. With each bite, you’ll experience the delightful combination of flavors that whisk you away to sunny shores. Sharing these cookies feels like giving a piece of joy, a personal touch that can lift spirits on any day. So, roll up your sleeves, gather your family, and dive into this baking adventure together. Trust me, the smiles you’ll create will be your sweetest rewards—go ahead and savor every delicious moment! Happy baking!