Crisp, buttery sugar cookies meet the tropical tang of caramelized pineapple in these Dreamy Pineapple Upside Down Sugar Cookies. The soft, chewy base provides the perfect canvas for the sweet and slightly tart topping, all finished with a glistening maraschino cherry. This unexpected combination of flavors and textures is a guaranteed crowd-pleaser.
These cookies take the comforting familiarity of a sugar cookie and elevate it with the bright, sunny flavors of a classic pineapple upside down cake. The secret lies in the buttery brown sugar caramel that not only adds a layer of decadent sweetness but also perfectly complements the acidity of the pineapple. These are ideal for parties, potlucks, or simply when you want a delightful twist on a traditional treat.
Why you’ll love this Dreamy Pineapple Upside Down Sugar Cookies with Pineapple Upside Down Cookies
- A fun and unique twist on classic pineapple upside down cookies.
- The chewy sugar cookie base is incredibly easy to make.
- The caramelized pineapple topping adds a burst of tropical flavor.
- Perfect for parties, holidays, or a special weekend treat.
- Requires only pantry-staple ingredients.
- Ready in under 40 minutes!
Ingredients & Substitutions
- 1/2 cup (1 stick) unsalted butter, softened
- 3/4 cup granulated sugar
- 1/4 cup packed light brown sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 1/4 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1/4 cup milk
- 1/4 cup unsalted butter, melted
- 1/2 cup packed light brown sugar (for topping) – Dark brown sugar can be used for a richer, molasses-like flavor.
- 1 (20 ounce) can pineapple slices, drained well and cut into smaller pieces – Ensure the pineapple is thoroughly drained to prevent soggy cookies.
- 18 maraschino cherries, halved
How to make Dreamy Pineapple Upside Down Sugar Cookies
Step 1: Prepare the oven and baking sheets.
Pineapple upside down cookies makes every moment feel velvety. Preheat oven to 375°F (190°C). Line baking sheets with parchment paper.
Step 2: Cream the butter and sugars.
In a large bowl, cream together the softened butter, granulated sugar, and 1/4 cup brown sugar until light and fluffy. Beat in the egg and vanilla extract.
Step 3: Combine the dry and wet ingredients.
In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, alternating with the milk, beginning and ending with the dry ingredients. Mix until just combined.
Step 4: Prepare the topping.
In a small bowl, combine the melted butter and 1/2 cup brown sugar (for topping). Stir until smooth.
Step 5: Assemble the cookies.
Drop rounded tablespoons of cookie dough onto the prepared baking sheets. Use your fingers or the back of a spoon to flatten the cookies slightly. Spoon a small amount of the butter-brown sugar mixture onto each cookie. Top with a few pieces of pineapple and half a maraschino cherry.
Step 6: Bake the cookies.
Bake for 10-12 minutes, or until the edges are lightly golden. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.
Tips for Success
- Ensure the butter is properly softened for smooth creaming.
- Drain the pineapple well to prevent soggy cookies.
- Don’t overbake the cookies; they should be slightly soft in the center.
- Let the cookies cool completely on a wire rack to prevent them from sticking.
Serving Suggestions
These Dreamy Pineapple Upside Down Sugar Cookies are delicious on their own, but they also pair well with a scoop of vanilla ice cream or a dollop of whipped cream. For a refreshing complement, serve them with a glass of iced tea or a tropical fruit smoothie. You could even serve these alongside something savory for contrast, like this bright and flavorful mango spinach salad.
Storage & Reheating
Store the cookies in an airtight container at room temperature for up to 3 days. If you live in a warmer climate, consider storing them in the refrigerator to prevent the caramel from becoming too soft. These cookies are best enjoyed at room temperature and do not require reheating. If you’re looking for another way to use sugar cookies, then this breakfast fried rice recipe has some great inspiration for your next meal.
Frequently Asked Questions
Can I freeze these cookies?
Yes, you can freeze these cookies. Place them in a single layer on a baking sheet and freeze until solid. Then, transfer them to an airtight container or freezer bag. They can be stored in the freezer for up to 2 months. Thaw at room temperature before serving.
Can I use fresh pineapple?
While canned pineapple is recommended for its consistent sweetness and texture, you can use fresh pineapple. Be sure to core it well and cut it into small, even pieces. You may need to adjust the baking time slightly, as fresh pineapple can release more moisture.
Can I make these cookies ahead of time?
Yes, you can make the cookie dough ahead of time and store it in the refrigerator for up to 2 days. Let the dough come to room temperature slightly before rolling and baking. You can also prepare the butter-brown sugar topping ahead of time and store it in an airtight container at room temperature.
These Dreamy Pineapple Upside Down Sugar Cookies are a delightful and unexpected treat that will leave you wanting more. The chewy cookie, the caramelized pineapple, and the sweet cherry create a symphony of flavors and textures that’s perfect for any occasion. Give this recipe a try and let us know what you think in the comments below!
Dreamy Pineapple Upside Down Sugar Cookies
These Pineapple Upside Down Sugar Cookies are a delightful twist on a classic dessert. Soft, chewy sugar cookies are topped with caramelized pineapple and a sweet cherry, creating a burst of tropical flavor in every bite. The buttery caramel complements the tangy pineapple, while the sugar cookie provides a comforting and familiar base. These cookies are perfect for parties, holidays, or anytime you crave a sweet treat. The chewy texture of the cookie, combined with the soft pineapple and gooey caramel, makes for an unforgettable dessert experience. Prepare to be amazed by this unexpected combination of flavors and textures that will leave you wanting more!
- Total Time: 37 minutes
- Yield: 18 cookies 1x
Ingredients
- 1/2 cup (1 stick) unsalted butter, softened
- 3/4 cup granulated sugar
- 1/4 cup packed light brown sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 1/4 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1/4 cup milk
- 1/4 cup unsalted butter, melted
- 1/2 cup packed light brown sugar (for topping)
- 1 (20 ounce) can pineapple slices, drained well and cut into smaller pieces
- 18 maraschino cherries, halved
Instructions
- Preheat oven to 375°F (190°C). Line baking sheets with parchment paper.
- In a large bowl, cream together the softened butter, granulated sugar, and 1/4 cup brown sugar until light and fluffy. Beat in the egg and vanilla extract.
- In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, alternating with the milk, beginning and ending with the dry ingredients. Mix until just combined.
- In a small bowl, combine the melted butter and 1/2 cup brown sugar (for topping). Stir until smooth.
- Drop rounded tablespoons of cookie dough onto the prepared baking sheets. Use your fingers or the back of a spoon to flatten the cookies slightly.
- Spoon a small amount of the butter-brown sugar mixture onto each cookie. Top with a few pieces of pineapple and half a maraschino cherry.
- Bake for 10-12 minutes, or until the edges are lightly golden. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.
Notes
For best results, ensure the pineapple is well-drained to prevent soggy cookies. Store in an airtight container at room temperature for up to 3 days. You can also substitute canned crushed pineapple for the pineapple slices, if preferred. For a richer flavor, use dark brown sugar for the topping.
Nutrition
- Serving Size: 1 cookie
- Calories: 185
- Sugar: 15g
- Sodium: 85mg
- Fat: 8g
- Saturated Fat: 5g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 28g
- Fiber: 0.5g
- Protein: 1g
- Cholesterol: 25mg