Description
Pineapple Upside-Down Cookies combine the classic flavors of pineapple and maraschino cherries with a soft, buttery cookie base in an easy-to-make, bite-sized treat. Featuring a caramelized brown sugar and butter topping with a juicy pineapple center, these cookies offer a delightful tropical twist on traditional upside-down desserts.
Ingredients
Scale
For the Topping:
- ½ cup light brown sugar (for topping)
- 2 tablespoons unsalted butter (melted)
- 12 maraschino cherries (halved)
- ½ cup crushed pineapple (drained)
For the Cookie Dough:
- 1 cup unsalted butter, softened
- 1 cup light brown sugar (packed)
- ½ cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 2¼ cups all-purpose flour
- 1 teaspoon baking powder
- ½ teaspoon baking soda
- ½ teaspoon salt
- ¼ cup pineapple juice
Instructions
- Preheat and prepare muffin tin: Preheat the oven to 350°F (175°C) and lightly grease or line a muffin tin with paper liners to prevent sticking.
- Make the topping mixture: In a small bowl, combine ½ cup light brown sugar with melted butter until well mixed. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup.
- Add fruit to topping: Place half a maraschino cherry in the center of each muffin cup on top of the sugar-butter mixture, then add a small spoonful of well-drained crushed pineapple over the cherry.
- Cream the butter and sugars: In a large bowl, cream together the softened butter, 1 cup light brown sugar, and ½ cup granulated sugar using a mixer until light and fluffy.
- Add eggs and vanilla: Beat in eggs one at a time, ensuring each is fully incorporated before adding the next, then mix in the vanilla extract.
- Combine dry ingredients: In a separate bowl, whisk together all-purpose flour, baking powder, baking soda, and salt to evenly distribute the leavening agents.
- Mix wet and dry ingredients: Gradually add the dry ingredients to the wet mixture, alternating with pineapple juice, mixing just until combined to avoid overworking the dough.
- Fill muffin cups: Spoon the cookie dough over the pineapple topping mixture in each muffin cup, filling about three-quarters full to allow room for rising.
- Bake the cookies: Place the muffin tin in the preheated oven and bake for 18–22 minutes or until the cookies are golden brown and a toothpick inserted in the center comes out clean.
- Cool and invert: Let the cookies cool in the tin for 5 minutes. Then carefully invert the tin onto a wire rack to release the cookies and reveal the pineapple upside-down topping. Serve warm or at room temperature.
Notes
- For added flavor, sprinkle a pinch of cinnamon into the brown sugar topping mixture.
- Ensure the crushed pineapple is well drained to prevent soggy cookies.
- These cookies can also be made in mini muffin tins for bite-sized treats, adjusting baking time accordingly.
