Pineapple Upside Down Sugar Cookies Recipe

If you’re craving a sweet treat that bursts with tropical vibes and nostalgic charm, the Pineapple Upside Down Sugar Cookies Recipe is an absolute must-try. Imagine classic sugar cookies transformed into mini caramelized pineapple delights topped with cherries, creating a perfect balance of buttery softness, fruity tang, and caramel-sweet glaze all in one bite. Whether you’re hosting a party or simply want a fun twist on cookie time, this recipe brings sunshine and smiles to any occasion with its charming presentation and irresistible flavor.

Ingredients You’ll Need

These ingredients may seem simple, but each one plays a crucial role in creating the perfect texture, flavor, and appearance of your Pineapple Upside Down Sugar Cookies. From the creamy butter to the tangy pineapple, every element combines to deliver that classic split of sweetness and richness.

• 1 cup unsalted butter, at room temperature: Ensures a creamy base for the cookie dough, adding softness and richness.
• 1 1/2 cups granulated sugar: Sweetens and helps with the cookie’s tender crumb and slight crisp edge.
• 2 large eggs: Provides structure and moisture, binding everything together.
• 2 teaspoons vanilla extract: Adds warm, inviting aromatics to enhance the overall flavor profile.
• 1/2 cup sour cream: Keeps the cookie tender and slightly tangy for a delightful contrast with the sweetness.
• 3 cups all-purpose flour: The foundation for your dough, creating the perfect cookie body.
• 1 teaspoon baking powder: Gives the cookies a light rise without making them cakey.
• 1 teaspoon cornstarch: Adds tenderness, preventing toughness in every bite.
• 1/2 teaspoon salt: Balances sweetness and enhances all flavors.
• 13 canned pineapple slices, drained: The tropical star of the show, delivering juicy burst and beautiful presentation.
• 13 maraschino cherries: Classic garnish that adds a pop of color and a hint of sweetness.
• 1/2 cup unsalted butter, melted: For the luscious brown sugar glaze, helping to caramelize the pineapple topping.
• 1 cup light brown sugar, packed: Combined with melted butter, it creates a rich, caramel-like sauce under the cookies.

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) and greasing your mini round cake pan or muffin tin carefully. This sets the stage for the luscious caramelized base and ensures your cookies release easily after baking.

Step 2: Cream Butter and Sugar

In a large bowl, use an electric mixer to cream the softened butter and granulated sugar until the mixture is light, fluffy, and pale. This is a critical step to incorporate air, giving your cookies a tender and slightly airy texture.

Step 3: Add Eggs, Vanilla, and Sour Cream

Mix in the eggs one at a time, followed by the vanilla extract and sour cream until fully combined. The sour cream adds moisture and a slight tang, balancing the sweetness for a beautiful cookie crumb.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. This ensures even distribution of leavening agents and seasoning, key for consistent texture throughout.

Step 5: Mix Dry Ingredients into Wet

Gradually add the flour mixture into the wet ingredients, mixing just until combined to avoid overworking the dough. This keeps your cookies soft and tender rather than dense and tough.

Step 6: Prepare the Brown Sugar Glaze

In another bowl, whisk melted butter and light brown sugar together until smooth and glistening. This glaze is what gives your cookies that irresistible caramelized pineapple base everyone loves.

Step 7: Assemble the Cookies

Drop about a tablespoon of the brown sugar mixture into each cavity of the prepared pan, spreading it evenly to coat the bottom. Then, gently place a pineapple slice over the brown sugar and nestle a maraschino cherry right in its center for that classic look.

Step 8: Add the Cookie Dough

Using a 3-tablespoon scoop, portion the cookie dough atop each pineapple ring. Flatten gently with an offset spatula so the dough evenly covers the fruit and brown sugar glaze, ensuring even baking and that iconic “upside down” effect.

Step 9: Bake to Perfection

Bake your cookies for 25 minutes until golden around the edges and the brown sugar glaze bubbles up the sides. This bubbling is your sign that the caramelization is happening, giving that signature sticky sweetness.

Step 10: Cool and Invert

Allow the cookies to cool in the pan for 10 minutes, then carefully invert them onto wax paper so the caramelized sugar and pineapple sit on top. This dramatic reveal is part of the fun and makes them look irresistible.

Step 11: Cool Completely and Store

Let the cookies cool fully before serving. Once cooled, store them in an airtight container to maintain freshness and that perfect chewy, buttery texture you’ll crave again and again.

How to Serve Pineapple Upside Down Sugar Cookies Recipe

Garnishes

For an extra pop of freshness, sprinkle finely chopped fresh mint or a light dusting of powdered sugar over your cookies just before serving. The mint adds a refreshing contrast that beautifully complements the sweet pineapple topping.

Side Dishes

Serve these cookies alongside a scoop of vanilla ice cream or a dollop of whipped cream for a simple but decadent dessert experience. The cold creaminess pairs wonderfully with the warm, gooey sweetness of the cookies.

Creative Ways to Present

Try arranging the cookies on a tropical-themed platter with fresh pineapple slices and cherries scattered around for an eye-catching display. They also make charming gifts when wrapped individually in cellophane with a ribbon, perfect for sharing your favorite Pineapple Upside Down Sugar Cookies Recipe with friends and family.

Make Ahead and Storage

Storing Leftovers

Keep any leftover cookies in an airtight container at room temperature for up to 4 days. This helps preserve their chewy texture and keeps the caramel glaze from hardening, so every bite stays delightfully soft and flavorful.

Freezing

You can freeze the unbaked cookie dough balls arranged on a baking sheet for up to 3 months. When ready, thaw slightly before baking as usual. This is a fantastic time-saver for spontaneous cookie cravings!

Reheating

Warm leftover cookies in a 300°F oven for 5 minutes or briefly in the microwave to revive their soft, buttery texture and give that caramel glaze a lovely shine. Just be careful not to overheat, or they might dry out.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! While canned pineapple slices are convenient and have a consistent texture, fresh pineapple rings can add a juicier, fresher taste. Just make sure to pat them dry so the cookies don’t get soggy.

What type of pan works best for this recipe?

A mini round cake pan or a muffin tin is ideal because it creates perfectly sized individual cookies with the classic pineapple upside down look. Larger pans might make assembly trickier and affect baking times.

How do I prevent the cookies from sticking when inverting?

Greasing your pan well and letting the cookies cool for about 10 minutes before inverting are key steps. If needed, carefully run a thin knife around the edges to loosen them, but be gentle to avoid breaking the cookies.

Can I use a different cherry variety?

Maraschino cherries are traditional and add both sweetness and vibrant color. However, you can experiment with brandied cherries or fresh cherries pitted and halved for a different flavor twist.

Is it possible to make these cookies vegan?

With some ingredient swaps like vegan butter, flax eggs, and dairy-free sour cream, you can adapt this Pineapple Upside Down Sugar Cookies Recipe for a vegan diet. Just keep in mind texture and flavor may vary slightly.

Final Thoughts

There’s nothing quite like the joyful surprise of biting into a Pineapple Upside Down Sugar Cookies Recipe cookie—sweet, buttery, and kissed with caramelized tropical fruit charm. I encourage you to give this recipe a try, whether it’s for a special occasion or a sunny pick-me-up on any day. It’s a fun, delicious way to bring a little sunshine to your kitchen and your heart!

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