If you have a sweet tooth and love a tropical twist in your treats, this Pineapple Upside-Down Sugar Cookies Recipe is about to become your new favorite indulgence. Imagine vibrant pineapple slices and cheerful maraschino cherries nestled beneath a layer of buttery, tender sugar cookie dough, all baked to golden perfection. These cookies capture the nostalgic charm of the classic pineapple upside-down cake but in a perfectly portable, bite-sized form. Whether you’re baking for a party or craving something special to brighten your afternoon, this recipe delivers sunshine and smiles in every bite.
Ingredients You’ll Need
Don’t let the ingredient list intimidate you; each component here is simple yet vital to achieving the perfect balance of flavor, texture, and color in these cookies. From the creamy butter that creates tenderness to the bright pineapple that lends juiciness, every item is a small but crucial player.
- 1 cup butter (room temperature): Provides richness and a tender crumb.
- 1 ½ cups granulated sugar: Sweetens and helps create that delightful cookie texture.
- 2 eggs: Bind everything together and add moisture.
- 2 teaspoons vanilla extract: Adds warmth and depth of flavor.
- ½ cup sour cream: Keeps the cookies soft and moist.
- 3 cups all-purpose flour: The foundation for structure and chew.
- 1 teaspoon baking powder: Helps the cookies rise just enough for a perfect bite.
- 1 teaspoon cornstarch: Adds softness and helps with tender texture.
- ½ teaspoon salt: Balances sweetness and enhances flavor.
- 13 canned pineapple slices: The star fruit, juicy and vibrant.
- 13 maraschino cherries: Adds a pop of color and sweetness.
- ½ cup melted butter: For that luscious brown sugar topping.
- 1 cup packed light brown sugar: Creates a caramel-like base beneath the fruit.
How to Make Pineapple Upside-Down Sugar Cookies Recipe
Step 1: Preheat and Prepare Your Pan
Start by heating your oven to 350°F (175°C). Lightly grease a mini round cake pan – this ensures your cookies will come out easily after baking and keep that perfect shape.
Step 2: Cream Butter and Sugar
In a large bowl, beat the room temperature butter with granulated sugar until it looks fluffy and light. This step is key because it incorporates air into the dough, giving you tender cookies.
Step 3: Add Eggs, Vanilla, and Sour Cream
Mix in the eggs one at a time, then stir in the vanilla extract and sour cream. Each of these adds moisture and flavor depth to your dough, making sure your cookies are soft and rich.
Step 4: Gradually Incorporate Dry Ingredients
Combine flour, baking powder, cornstarch, and salt in a separate bowl, then slowly add to the wet ingredients. Keep mixing until you form a smooth dough that’s easy to scoop but still holds together well.
Step 5: Prepare the Brown Sugar Topping
In another bowl, stir together the melted butter and packed brown sugar. This glossy, sweet mixture will create that signature caramelized layer beneath the pineapple and cherries.
Step 6: Assemble Cookies
Spoon about a tablespoon of the brown sugar mixture into each mini cake cavity. Place a pineapple slice on top, then nestle a maraschino cherry in the center. This layering hints at the classic dessert and makes each cookie visually inviting.
Step 7: Add the Cookie Dough
Put about three tablespoons of cookie dough on top of each pineapple slice, gently pressing it to cover the fruit completely. This seals in all that lovely caramel flavor and fruit juice during baking.
Step 8: Bake and Cool
Bake the cookies for 25 minutes or until they’re golden brown on top. Let them cool in the pan for about 10 minutes to firm up, then carefully turn them out onto wax paper to cool fully. Once cooled, you’ll have a batch of incredible Pineapple Upside-Down Sugar Cookies ready to enjoy.
How to Serve Pineapple Upside-Down Sugar Cookies Recipe
Garnishes
For an extra touch of charm, dust these cookies with some powdered sugar or drizzle a bit of simple vanilla glaze on top. Adding a tiny fresh mint leaf also complements the tropical pineapple flavor beautifully.
Side Dishes
Serve these cookies alongside a scoop of vanilla ice cream or a dollop of whipped cream for a delightful dessert experience. They also pair wonderfully with a hot cup of coffee or a refreshing iced tea, balancing the sweetness perfectly.
Creative Ways to Present
Use a colorful serving tray decorated with fresh pineapple chunks and cherries for a festive look. You can also stack these cookies like mini towers or serve them on cocktail sticks for an easy-to-grab party treat that will wow your guests.
Make Ahead and Storage
Storing Leftovers
You can keep leftover Pineapple Upside-Down Sugar Cookies in an airtight container at room temperature for up to 3 days. This keeps them soft and fresh without drying out.
Freezing
If you want to save these tropical delights for later, freeze them in a single layer on a baking sheet first, then transfer to a freezer-safe container or bag. They can last up to 2 months frozen and thaw beautifully at room temperature.
Reheating
Warm the cookies gently in a low oven (about 300°F) for 5–7 minutes to bring back their soft texture and enhance the caramel notes. Avoid microwaving, which might make the cookies too soft or chewy.
FAQs
Can I use fresh pineapple instead of canned slices?
Absolutely! Just make sure to cut fresh pineapple into similarly sized slices and pat them dry well to avoid excess moisture in the cookies, which could affect the texture.
What if I don’t have a mini round cake pan?
You can try using a mini muffin tin or even cupcake liners; just adjust the amount of dough and baking time accordingly. The key is having individual compartments for each cookie’s layers.
Can I substitute sour cream with yogurt?
Yes, plain Greek yogurt works as a great substitute for sour cream in this recipe, offering similar moisture and tanginess that help keep your cookies soft.
How long do these cookies keep their freshness?
Stored properly in an airtight container, these cookies stay fresh for about 3 days at room temperature. Beyond that, you might notice a slight change in softness.
Is there a way to make this recipe dairy-free?
You can use plant-based butter and a dairy-free yogurt alternative instead of sour cream to make this recipe suitable for dairy-free diets while still maintaining great flavor and texture.
Final Thoughts
These Pineapple Upside-Down Sugar Cookies Recipe blends nostalgic flavors with a fresh twist that’s both fun and delicious to bake and share. Whether you’re treating yourself or bringing joy to friends and family, these cookies will brighten any day with their sunny, sweet charm. I can’t wait for you to try making them and discover just how wonderful this little tropical party in cookie form really is!
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Pineapple Upside-Down Sugar Cookies Recipe
- Total Time: 45 minutes
- Yield: 13 servings 1x
Description
Delight your taste buds with these Pineapple Upside Sugar Cookies, a tropical twist on classic sugar cookies featuring juicy pineapple slices and maraschino cherries baked right into each sweet, buttery treat. Perfect for parties or a fun dessert, these cookies combine soft sugar cookie dough with the caramelized flavors of a pineapple upside-down cake in a charming, handheld form.
Ingredients
Cookie Dough
- 1 cup butter (room temperature)
- 1 ½ cups granulated sugar
- 2 eggs
- 2 teaspoons vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- ½ teaspoon salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup melted butter
- 1 cup packed light brown sugar
Instructions
- Preheat Oven and Prepare Pan: Preheat your oven to 350°F (175°C). Lightly grease a mini round cake pan to prevent sticking and allow for easy removal of cookies after baking.
- Cream Butter and Sugar: In a large mixing bowl, cream together the room temperature butter and granulated sugar using a hand mixer or stand mixer until the mixture is fluffy and light in color, about 3-5 minutes.
- Add Wet Ingredients: Mix in the eggs one at a time, followed by the vanilla extract and sour cream, ensuring all ingredients are combined well to form a smooth batter.
- Incorporate Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt to the wet mixture. Stir until a soft dough forms, being careful not to overmix.
- Prepare Topping Mixture: In a separate bowl, combine the melted butter and packed light brown sugar until fully mixed, creating a rich caramel-like topping.
- Assemble Cookies: Spread about 1 tablespoon of the brown sugar and butter mixture into each cavity of the mini cake pan. Place one canned pineapple slice on top of the sugar mixture in each cavity, then place one maraschino cherry in the center of each pineapple slice.
- Add Cookie Dough on Top: Spoon approximately 3 tablespoons of cookie dough on top of each pineapple slice and cherry, pressing gently to cover the fruit and spread the dough evenly.
- Bake: Bake the cookies in the preheated oven for 25 minutes or until the edges are golden brown and the tops are set.
- Cool and Remove: Allow the cookies to cool in the pan for about 10 minutes. After cooling slightly, carefully turn the cookies out onto wax paper or a wire rack to cool completely before serving.
Notes
- Use a mini round cake pan for best shape and size consistency.
- Ensure butter is at room temperature for easier creaming with sugar.
- You can substitute canned pineapple slices with fresh pineapple rings if desired, but adjust baking time accordingly due to moisture content.
- Press dough gently over the pineapple slices to avoid tearing or breaking the topping.
- Allow cookies to cool completely before removing from pan to maintain their structure.
- Prep Time: 20 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
