If you’re searching for a charming twist on classic treats, the Pineapple Upside-Down Sugar Cookies Recipe is an absolute must-try. These cookies capture all the nostalgic flavors of the beloved pineapple upside-down cake, but in a delightful handheld form. Each bite offers a tender sugar cookie base topped with a luscious pineapple caramel and the perfect pop of a maraschino cherry, making them irresistibly sweet and visually stunning. Whether you’re treating family, sharing with friends, or simply craving something special, these cookies bring tropical sunshine and cozy comfort all at once.
Ingredients You’ll Need
The beauty of this Pineapple Upside-Down Sugar Cookies Recipe lies in its simplicity. The ingredients are everyday staples but come together in a way that creates an exciting medley of buttery, sweet, and fruity flavors. Each component plays a key role, from the fluffy sugar cookie dough to the rich pineapple caramel topping that makes these cookies shine.
- Unsalted butter, 1/2 cup softened: Provides richness and a tender crumb to the cookie dough.
- Granulated sugar, 1 cup: Sweetens the dough and helps achieve a light, fluffy texture.
- Large egg, 1: Binds ingredients and adds moisture.
- Vanilla extract, 1 teaspoon: Enhances flavor with warm, aromatic notes.
- All-purpose flour, 1 1/2 cups: The base structure for the cookies, yielding a soft, chewy bite.
- Baking soda, 1/2 teaspoon: Helps the cookies rise just enough for a tender texture.
- Salt, 1/4 teaspoon: Balances sweetness and elevates other flavors.
- Maraschino cherries, 1/4 cup chopped: Offers a bright pop of color and a sweet, fruity accent.
- Crushed pineapple, 1/2 cup drained: The star of the topping, bringing fresh tropical sweetness.
- Brown sugar, 1 tablespoon: Used in the caramel topping to add depth and richness.
- Unsalted butter, 2 tablespoons (for topping): Creates the smooth, buttery pineapple caramel that crowns each cookie.
How to Make Pineapple Upside-Down Sugar Cookies Recipe
Step 1: Prepare the Oven and Baking Sheet
Start by preheating your oven to 350°F (175°C). This ensures the perfect baking temperature from the moment your cookies go in. Line a baking sheet with parchment paper to prevent sticking and make cleanup a breeze.
Step 2: Cream Butter and Sugar
In a large bowl, whip the softened butter and granulated sugar together until the mixture is light, fluffy, and pale. This crucial step aerates the dough, resulting in those tender, melt-in-your-mouth sugar cookies that everyone loves. Next, beat in the egg and vanilla extract until fully combined to impart moisture and aroma.
Step 3: Combine Dry Ingredients
In a separate bowl, whisk together the flour, baking soda, and salt. Introducing the dry ingredients gradually into your wet mixture helps prevent overmixing, which could make the cookies tough. Mix until just combined, aiming for a smooth dough without overworking it.
Step 4: Make the Pineapple Caramel Topping
Now it’s time to bring on the luscious pineapple twist. In a small saucepan over medium heat, melt 2 tablespoons of unsalted butter. Add the brown sugar and stir frequently, cooking until the mixture transforms into a silky caramel. This sweet, buttery base is what makes these cookies extra special.
Step 5: Add the Pineapple
Once the caramel is ready, fold in the drained crushed pineapple and allow the mixture to cool slightly. This step ensures the pineapple flavor is perfectly melded into the topping while preventing it from melting the cookie dough when added.
Step 6: Portion the Cookie Dough
Using a tablespoon, scoop portions of cookie dough onto the prepared baking sheet, spacing them about 2 inches apart. This spacing helps the cookies spread just right without merging into one another.
Step 7: Add the Pineapple Topping and Cherries
Press a small indentation into the center of each dough ball. Spoon a small amount of the pineapple caramel mixture into each indentation, then top with a piece of chopped maraschino cherry. This not only locks in flavor but adds that iconic upside-down cake look to your cookie creations.
Step 8: Bake to Perfection
Bake in your preheated oven for 10 to 12 minutes or until the cookie edges turn a beautiful golden brown. Once out of the oven, let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack. Cooling fully allows the flavors to set and the cookies to firm up just right.
How to Serve Pineapple Upside-Down Sugar Cookies Recipe
Garnishes
Adding a sprinkle of toasted coconut flakes or a light dusting of powdered sugar over your Pineapple Upside-Down Sugar Cookies Recipe can elevate their tropical vibe even further. Fresh mint leaves can also create a lively contrast and add a refreshing note on the plate.
Side Dishes
These cookies pair wonderfully with a scoop of vanilla bean ice cream or a dollop of whipped cream, turning this snack into a mini dessert celebration. For drinks, a chilled cup of tropical iced tea or a tangy lemonade complements the sweet and fruity flavors perfectly.
Creative Ways to Present
For a festive gathering, arrange the cookies on a wooden serving board garnished with pineapple wedges and cocktail umbrellas for a playful touch. Alternatively, serve them in decorative cupcake liners to make individual treats that feel extra special.
Make Ahead and Storage
Storing Leftovers
You can keep leftover cookies fresh by storing them in an airtight container at room temperature for up to 4 days. This helps maintain their soft texture and keeps the pineapple topping luscious without drying out.
Freezing
If you want to enjoy these gems later, freezing is a great option. Place baked cookies in a single layer on a baking sheet to freeze initially, then transfer them to a freezer-safe container or bag for up to 3 months. Thaw at room temperature before serving.
Reheating
To bring a little warmth back to your cookies, pop them in a preheated oven at 300°F (150°C) for 5 minutes or microwave briefly for 10-15 seconds. This softens the cookies and revives the gooey caramel pineapple topping beautifully.
FAQs
Can I use fresh pineapple instead of canned crushed pineapple?
Absolutely! Finely chop fresh pineapple and ensure you drain it well before adding to the caramel topping. This keeps the cookies from becoming too wet and preserves the luscious texture.
What’s the best way to soften butter for this recipe?
Leave the butter out at room temperature for about 30 to 60 minutes before baking. It should be soft enough to press lightly with your finger without melting or feeling greasy.
Can I substitute maraschino cherries with fresh cherries?
You can, but fresh cherries will yield a different flavor and texture. Maraschino cherries lend a distinctive sweetness and bright color that’s iconic in this recipe, so keep that in mind.
Are these cookies gluten-free?
Not as written. However, you can experiment by using a gluten-free all-purpose flour blend that measures cup-for-cup, but results may vary slightly in texture.
How do I prevent the pineapple topping from making the cookie dough soggy?
Ensuring the pineapple is well-drained before mixing it with the caramel topping is key. Also, allow the caramel pineapple mixture to cool slightly before spooning it onto the dough to prevent premature melting.
Final Thoughts
Sharing the Pineapple Upside-Down Sugar Cookies Recipe has been such a joy because it combines nostalgic flavors with a fun, fresh twist. These cookies are more than just a treat; they’re a little bite of tropical happiness that’s perfect for any occasion. Give them a try, and I promise they’ll become a new favorite in your baking repertoire!
Print
Pineapple Upside-Down Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 12 minutes
- Total Time: 27 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
Delight in these Pineapple Upside-Down Sugar Cookies, a tropical twist on classic sugar cookies. With a sweet caramelized pineapple topping and a maraschino cherry crown, these cookies are soft, flavorful, and perfect for any occasion.
Ingredients
Cookie Dough
- 1/2 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
Topping
- 1/4 cup maraschino cherries, chopped
- 1/2 cup crushed pineapple, drained
- 1 tablespoon brown sugar
- 2 tablespoons unsalted butter
Instructions
- Preheat Oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking and ensure even baking.
- Cream Butter and Sugar: In a large bowl, cream together the softened butter and granulated sugar until the mixture is light and fluffy. Beat in the egg and vanilla extract until well combined for a smooth dough base.
- Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually add these dry ingredients to the wet ingredients and mix until just combined to avoid overworking the dough.
- Prepare Caramel Topping: Melt 2 tablespoons of unsalted butter in a small saucepan over medium heat. Stir in the brown sugar and cook, stirring frequently until it forms a smooth caramel sauce.
- Incorporate Pineapple: Remove the caramel from heat and fold in the drained crushed pineapple. Allow the mixture to cool slightly to thicken before using.
- Form Dough on Sheet: Scoop tablespoon-sized portions of the cookie dough onto the prepared baking sheet, spacing each about 2 inches apart to allow spreading.
- Add Topping: Press a small indentation into the center of each dough portion. Spoon a small amount of the pineapple caramel into the indentation and top with a piece of chopped maraschino cherry for the signature look and flavor.
- Bake: Bake the cookies in the preheated oven for 10-12 minutes, or until the edges turn golden brown, indicating they are done.
- Cool and Serve: Remove the cookies from the oven and allow them to cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely and set.
Notes
- Ensure pineapple is well-drained to prevent excess moisture impacting cookie texture.
- You can substitute maraschino cherries with glacé cherries or fresh cherries if preferred.
- For softer cookies, do not overbake and remove as soon as edges are golden.
- Store cookies in an airtight container at room temperature for up to 3 days.
