Pineapple Upside Down Cookie
These Pineapple Upside Down Cookies are a tropical, buttery delight topped with caramelized pineapple and cherries. Perfectly soft, sweet, and irresistibly nostalgic!
Servings: 12 servings
Ingredients
- 1 cup unsalted butter softened
- 1 cup granulated sugar
- 2 large eggs
- 1 cup all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
- 1 teaspoon vanilla extract
- 1 cup crushed pineapple drained
- 1/2 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 sticking.
- Prepare the topping: In a small bowl, combine the brown sugar and drained crushed pineapple. Set aside so the flavors can meld.
- Cream the butter and sugar: In a large bowl, beat the softened butter and granulated sugar together until light and fluffy – about 3-4 minutes. This step is key for a tender cookie.
- Add eggs and vanilla: Beat in the eggs one at a time, followed by the vanilla extract, ensuring everything is well combined.
- Mix dry ingredients: In another bowl, whisk together the flour, baking powder, baking soda, and salt.
- Combine wet and dry: Gradually add the dry ingredients into the wet mixture, stirring just until combined. Avoid overmixing to keep the cookies soft.
- Shape the cookies: Using a tablespoon or cookie scoop, portion out the dough onto your prepared baking sheet, spacing them about 2 inches apart.
- Add the pineapple topping: Spoon a small amount of the pineapple and brown sugar mixture onto each cookie dough mound. Gently press a maraschino cherry into the center of each cookie on top of the pineapple.
- Bake: Place the baking sheet in the oven and bake for 12-15 minutes, or until the edges are golden and the cookies are set.
- Cool and serve: Allow the cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely. This helps the topping set perfectly.
Equipment
- Baking Sheet
- Parchment Paper
- Mixing Bowls
- Electric Mixer
- Measuring Cups
- Measuring Spoons
- Cookie Scoop
Notes
- Drain the crushed pineapple thoroughly to avoid soggy dough and spreading cookies.
- Use room temperature butter and eggs for a smoother dough and better texture.
- Do not overmix the dough once dry ingredients are added to keep cookies tender.
- Chill the dough for 15-20 minutes if it feels too soft or your kitchen is warm to prevent spreading.
- Try variations like adding shredded coconut, nuts, chocolate chips, or warm spices for new flavors.