If you’re craving something uniquely delightful with a burst of tropical charm, this Pineapple Upside Down Sugar Cookies Recipe is your new best friend in the kitchen. These cookies perfectly combine the classic buttery sugar cookie base with the rich caramelized flavor of pineapple and brown sugar, plus that cheerful pop of a maraschino cherry on top. Each bite brings a perfect balance of sweetness and a subtle tang that’s hard to resist. They’re not only fun to make but also a guaranteed crowd-pleaser that brightens any gathering or simply satisfies a sweet tooth craving in a spectacular way.

pineapple upside down sugar cookies ingredients flat lay: fresh golden yellow canned pineapple slices neatly stacked, bright glossy red maraschino cherries placed beside, smooth pale yellow unsalted butter chunks at room temperature arranged in a small bowl, granulated white sugar in a small glass jar with a tiny wooden spoon, light and fluffy brown sugar with warm caramel tones in a rustic ceramic bowl, two large brown eggs cracked open showing rich orange yolks in a clear glass bowl, creamy white sour cream in a white porcelain ramekin, vanilla extract bottle with amber liquid and natural cork stopper, all-purpose flour scattered gently on the clean white surface with a small wooden scoop resting on top, baking powder, fine white cornstarch, and coarse salt in tiny white porcelain spoons lined up horizontally, melted butter in a small glass measuring cup showing glossy golden texture, arranged aesthetically on a smooth white marble countertop with soft natural light casting gentle shadows, minimalistic modern styling with subtle hints of rustic warmth, a few green leaves from a pineapple plant subtly placed for color contrast, clean and crisp edges, fresh and vibrant colors, emphasis on textures and contrast, overhead shot, top down view, flat lay photography, professional food styling --ar 1:1 --q 2 --s 750 --v 6.1

Ingredients You’ll Need

Gathering a few simple, straightforward ingredients is the key to creating these luscious cookies, and each one plays an important role in building the texture and flavor. Using quality butter, fresh eggs, and the perfect mix of dry ingredients sets the foundation for a wonderfully tender yet sturdy cookie. The pineapple slices and cherries add both eye-catching color and a burst of fruity sweetness that makes these cookies truly stand out.

1 cup unsalted butter, at room temperature: Ensures a creamy, smooth dough and a rich buttery flavor.
1 1/2 cups granulated sugar: Adds sweetness and helps create a light, fluffy texture when creamed with butter.
2 large eggs: Binds ingredients and contributes moisture and structure.
2 teaspoons vanilla extract: Enhances overall flavor with a warm, fragrant touch.
1/2 cup sour cream: Adds moistness and a slight tang, making the tender crumb even better.
3 cups all-purpose flour: Forms the body of the cookie, providing the right amount of chewiness.
1 teaspoon baking powder: Helps the cookies rise just enough for a light texture.
1 teaspoon cornstarch: Keeps the cookies tender by softening the gluten.
1/2 teaspoon salt: Balances sweetness and deepens flavors.
13 canned pineapple slices, drained: Adds the signature tropical twist and juicy brightness.
13 maraschino cherries: Provides a classic, colorful centerpiece bursting with sweetness.
1/2 cup unsalted butter, melted: Used to create the luscious brown sugar glaze that caramelizes beautifully.
1 cup light brown sugar, packed: Combines with melted butter to produce that irresistible caramel topping.

How to Make Pineapple Upside Down Sugar Cookies Recipe

Step 1: Prepare Your Pan and Oven

Start by preheating your oven to 350°F (175°C) so it’s ready to go when your dough is mixed. Grease a mini round cake pan or a muffin tin to make sure your cookies won’t stick when it’s time to flip them out. This prep step is crucial to getting that beautiful pineapple-caramel topping to release perfectly.

Step 2: Cream Butter and Sugar

In a large mixing bowl, cream together the room temperature butter and granulated sugar using an electric mixer until the mixture becomes light and fluffy. This not only melds those two ingredients but also traps air that will help give your cookies a delightful texture.

Step 3: Add Wet Ingredients

Next, incorporate the eggs one at a time, followed by the vanilla extract and sour cream. Mix thoroughly until everything is smoothly combined. The sour cream adds a lovely moistness and a subtle tang that balances the sweetness perfectly.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. This ensures that your leavening agents and salt are evenly distributed throughout the dough, preventing any lumps or uneven rising.

Step 5: Mix Wet and Dry Ingredients

Gradually add the dry ingredients into the wet mixture, mixing just until combined. Be careful not to overmix, as that could yield tough cookies. Once your dough comes together, set it aside while you prepare the caramel glaze and fruit topping.

Step 6: Prepare Brown Sugar Glaze

In another bowl, blend the melted butter with the light brown sugar until smooth. This mixture will form that luscious caramel base that bubbles and crisps up under each cookie, echoing the traditional pineapple upside-down cake flavors.

Step 7: Assemble Cookies with Fruit

Spoon about 1 tablespoon of the brown sugar glaze evenly into each cavity of your prepared pan. Then, lay one pineapple slice over each sugary bed, and nestle a maraschino cherry right in the center of every pineapple ring. This little detail creates that iconic look and flavor.

Step 8: Add Cookie Dough

Using a 3-tablespoon scoop, portion cookie dough on top of each fruit-topped cavity. Gently press down and flatten the dough using an offset spatula to ensure even baking and that lovely caramel glaze can bubble up around the edges.

Step 9: Bake Your Cookies

Place the pan in the preheated oven and bake for about 25 minutes. Keep an eye out for the cookies to turn golden around the edges and the brown sugar glaze to become bubbly—an inviting sign that magic is happening.

Step 10: Cool and Invert

Once baked, allow the cookies to cool in the pan for 10 minutes. Then carefully invert them onto a sheet of wax paper. This step is where the caramel glaze beautifully drapes over the cookie tops, creating that irresistible Pineapple Upside Down Sugar Cookies Recipe finish.

Step 11: Final Cooling

Let the cookies cool completely before digging in. This resting time lets the caramel set perfectly, ensuring a sticky, yet perfectly chewy treat every time. Store in an airtight container to keep them fresh.

How to Serve Pineapple Upside Down Sugar Cookies Recipe

Garnishes

These cookies are already stunning, but a light dusting of powdered sugar or a small sprig of fresh mint can add a lovely touch of elegance and freshness. They also pair wonderfully with a drizzle of white chocolate or a sprinkle of toasted coconut for extra island vibes.

Side Dishes

Serve your Pineapple Upside Down Sugar Cookies Recipe alongside a scoop of vanilla ice cream or a dollop of whipped cream to balance the sweetness with creamy coolness. A cup of strong coffee or tropical fruit punch also complements their rich, caramelized flavor perfectly.

Creative Ways to Present

For a party, arrange these cookies on a pineapple-shaped platter or place them on a bed of fresh pineapple leaves for an eye-catching centerpiece. You could also stack them with thin layers of cream cheese frosting for a playful cookie “cake” that amazes your guests.

Make Ahead and Storage

Storing Leftovers

Keep any leftover Pineapple Upside Down Sugar Cookies Recipe fresh by storing them in an airtight container at room temperature. They will maintain their chewy texture and moisture for up to 4 days, making them a perfect treat to enjoy throughout the week.

Freezing

If you want to make these ahead of time, you can freeze the unbaked cookie dough scoops on a sheet before baking. Once frozen solid, transfer them to a freezer-safe bag. Bake directly from frozen, adding a couple of minutes to the baking time. Alternatively, baked cookies can also be frozen in an airtight container for up to 3 months.

Reheating

To revive the fresh-baked feel, gently warm the cookies in the oven at 300°F for 5-7 minutes or microwave for 10-15 seconds. This softens the caramel glaze and brings the buttery flavors back to life, perfect for when you want to impress without baking anew.

FAQs

Can I use fresh pineapple instead of canned?

Fresh pineapple can add a lovely freshness, but be sure to slice it thinly and drain any excess juice to avoid soggy cookies. Canned pineapple slices are easier to manage because they’re already tenderized and consistently sized.

What if I don’t have a mini cake pan or muffin tin?

You can use any small round baking dish or even a mini tart pan that holds individual portions, but remember to grease it well. Adjust the baking time slightly if your cavities are larger or smaller to avoid under- or over-baking.

Can I substitute the sour cream?

Yes, plain Greek yogurt is a great substitute that offers similar moisture and tang. Avoid using low-fat versions as they might affect the cookie’s texture.

Are these cookies gluten-free friendly?

This recipe uses all-purpose flour, so it’s not gluten-free as is. For a gluten-free version, try using a 1-to-1 gluten-free baking flour blend that includes xanthan gum to maintain the texture.

How do I make sure the cookies don’t stick when inverted?

Greasing your pan very well is essential, or you can use parchment liners if they fit your pan. Also, letting the cookies cool for the recommended 10 minutes ensures the caramel glaze sets just enough to release cleanly without tearing.

Final Thoughts

This Pineapple Upside Down Sugar Cookies Recipe is a fun, fresh spin on two classic favorites that will have you smiling with every bite. Easy enough to whip up anytime but special enough to impress guests, these cookies bring tropical sunshine into your kitchen. Grab your ingredients, invite a friend over, and get ready to make sweet memories with this scrumptious recipe!