Pineapple Upside Down Cookie
This Pineapple Upside Down Cookie is a chewy, tropical treat bursting with caramelized pineapple and a pop of maraschino cherry on soft, buttery cookie dough.
Servings: 24 servings
Ingredients
- 1 cup unsalted butter softened
- 1 cup granulated sugar
- 2 large eggs
- 1 cup all-purpose flour
- 1 teaspoon baking powder
- 0.5 teaspoon baking soda
- 0.25 teaspoon salt
- 1 teaspoon vanilla extract
- 1 cup crushed pineapple well drained
- 0.5 cup brown sugar packed
- Maraschino cherries for topping
Instructions
- Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat to prevent the cookies from sticking and ensure even baking.
- In a small bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. Set this aside for later use.
- In a large mixing bowl, use an electric mixer to cream the softened unsalted butter with the granulated sugar until the mixture is light and fluffy—about 3 to 4 minutes.
- Beat in the eggs one at a time, fully incorporating each before adding the next. Then stir in the vanilla extract.
- Gradually add the dry ingredients to the wet mixture, mixing gently just until everything is combined. Avoid over-mixing to keep your cookies soft.
- In a small bowl, toss the drained crushed pineapple with the brown sugar until well coated. This mixture will create the signature caramelized, fruity topping for your cookies.
- Spoon cookie dough onto your prepared baking sheet in evenly sized mounds (about 1.5 tablespoons each). Then, carefully press a spoonful of the pineapple and brown sugar mixture on top of each cookie. Finish each with a maraschino cherry pressed gently into the center.
- Bake the cookies for 12 to 15 minutes, or until the edges are golden and the centers are just set. Keep an eye on them to preserve that soft texture.
- Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a cooling rack. This helps the topping set nicely without sticking.
Equipment
- Mixing Bowls
- Electric mixer or sturdy whisk
- Measuring cups and spoons
- Baking sheet lined with parchment paper or silicone mat
- Cooling rack
- Spatula
Notes
- Drain pineapple thoroughly to avoid soggy cookies.
- Use brown sugar for the topping to achieve authentic caramelization.
- Press fruit topping gently on cookies, don’t mix it into the dough.
- Chill dough 15-30 minutes before baking to prevent spreading.
- Store cookies in an airtight container at room temperature for up to 4 days or freeze for up to 3 months.