These Pineapple Upside-Down Sugar Cookies offer a delicious twist on the classic pineapple upside-down cake. With a soft, chewy sugar cookie base and a caramelized pineapple topping, they’re a perfect treat for summer or any time you want a tropical-inspired dessert. These cookies are fun, flavorful, and easy to make, offering a unique dessert experience that combines the best of both worlds!

Why You’ll Love This Recipe

Tropical Flavor: The sweet, tangy pineapple adds a refreshing burst of flavor.
Chewy Texture: Soft sugar cookies provide the perfect base.
Festive: These cookies are perfect for holiday gatherings, summer parties, or just a sweet treat.

Ingredients

For the Cookie Base

Butter: Adds a rich flavor and soft texture to the cookies.
Sugar: Sweetens the cookies and contributes to their chewy texture.
Egg: Helps bind the dough together.
Vanilla extract: Adds depth of flavor to the cookies.
All-purpose flour: Forms the base of the cookie dough.
Baking soda: Helps the cookies rise slightly.
Salt: Balances the sweetness.

For the Pineapple Topping

Pineapple slices: The star of the topping, adding tropical sweetness.
Brown sugar: Caramelizes the pineapple and adds sweetness.
Butter: Helps create a rich, golden syrup with the brown sugar.
Maraschino cherries: For the traditional pineapple upside-down cake effect and a pop of color.

Instructions

Step 1: Prepare the Pineapple Topping

Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.
In a small saucepan, melt butter over medium heat. Add brown sugar and stir until the sugar is dissolved and the mixture is bubbly.
Place pineapple slices on the prepared baking sheet, ensuring they are evenly spaced. Place a maraschino cherry in the center of each pineapple ring. Drizzle the sugar-butter mixture over the pineapple slices. Set aside.

Step 2: Make the Cookie Dough

In a large mixing bowl, cream together butter and sugar until light and fluffy.
Add the egg and vanilla extract, and mix until fully incorporated.
In a separate bowl, whisk together flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a dough forms.

Step 3: Form and Bake the Cookies

Scoop tablespoon-sized portions of cookie dough and gently roll them into balls. Place each dough ball on top of a pineapple slice on the prepared baking sheet.
Gently press down on each dough ball to flatten it slightly.
Bake for 10-12 minutes, or until the edges of the cookies are golden and set.

Step 4: Cool and Serve

Allow the cookies to cool on the baking sheet for 5 minutes, then carefully transfer them to a wire rack to cool completely.
Serve the cookies with the pineapple topping facing up for a fun and tropical presentation.

Tips for Success

Pineapple Rings: Make sure to use well-drained pineapple slices to avoid excess moisture.
Chill the Dough: If the dough feels too soft to handle, chill it in the fridge for 30 minutes to make it easier to work with.
Cookie Base Texture: Don’t overmix the dough to keep the cookies soft and chewy.

Nutrition Facts (per cookie)

Servings: 16 cookies
Calories: 170
Total Fat: 7g
Saturated Fat: 4g
Cholesterol: 20mg
Sodium: 90mg
Carbohydrates: 26g
Fiber: 1g
Sugar: 14g
Protein: 1g

FAQ

Q1: Can I make these cookies ahead of time?
A1: Yes, the cookies can be made a day or two ahead of time. Store them in an airtight container at room temperature.

Q2: Can I use fresh pineapple instead of canned?
A2: Absolutely! Just make sure to slice the fresh pineapple thinly and remove excess moisture before using.

Q3: Can I use another fruit instead of pineapple?
A3: You can try other fruits like peaches or pears for a different twist on this cookie.

Q4: Can I freeze these cookies?
A4: Yes, freeze the cookies in a single layer on a baking sheet before transferring them to a freezer bag for up to 3 months.

Q5: Can I use coconut sugar instead of brown sugar?
A5: Coconut sugar can be used as a substitute, but it may slightly alter the flavor and color of the cookies.

Q6: What can I use if I don’t have maraschino cherries?
A6: You can omit the cherries or replace them with other small, sweet fruit such as red currants or cranberries.

Q7: How can I make the topping more caramelized?
A7: Allow the topping to bake a bit longer to ensure a deeper caramelization, but keep an eye on it to avoid burning.

Q8: Can I add a glaze to these cookies?
A8: Yes, a simple glaze made from powdered sugar and milk can be drizzled over the cookies for extra sweetness.

Q9: What other decorations can I use for these cookies?
A9: Consider adding toasted coconut flakes or crushed nuts for extra texture and flavor.

Q10: How can I make the dough more flavorful?
A10: Add a pinch of cinnamon or nutmeg to the dough for a more aromatic touch.

These Pineapple Upside-Down Sugar Cookies are the perfect combination of tropical sweetness and comfort. Enjoy these fun treats at your next gathering or as a special dessert for the holidays!