Description
These Pineapple Upside-Down Cookies offer a delightful twist on the classic dessert, featuring a tender, buttery cookie base topped with sweet caramelized brown sugar, pineapple, and maraschino cherries. Baked in a muffin tin, they are perfectly portioned, combining a soft, moist interior with a sticky, fruity topping that makes them irresistible for any occasion.
Ingredients
Scale
For the Topping
- 1/3 cup brown sugar
- 2 tablespoons unsalted butter, melted
- 12 maraschino cherries, halved
- 1/2 cup crushed pineapple, drained
For the Cookies
- 1/2 cup unsalted butter, softened
- 1/2 cup brown sugar, packed
- 1/4 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
- 1/4 cup pineapple juice (reserved from draining crushed pineapple)
Instructions
- Prepare the muffin tin topping: Preheat your oven to 350°F (175°C) and grease a standard muffin tin thoroughly. In a small bowl, combine the 1/3 cup brown sugar with the melted butter. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup. Place a halved cherry in the center of each cup, then top with approximately 1 teaspoon of well-drained crushed pineapple. This creates the signature upside-down topping.
- Mix the cookie dough base: In a large mixing bowl, cream together the softened unsalted butter, 1/2 cup packed brown sugar, and 1/4 cup granulated sugar until the mixture is light and fluffy. This may take about 3 to 4 minutes with a mixer. Beat in the egg and vanilla extract until well incorporated.
- Combine dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to distribute the leavening agents evenly in the flour.
- Integrate wet and dry components: Gradually add the dry flour mixture to the wet ingredients, alternating with the reserved pineapple juice. Start and end with the dry ingredients, mixing just until combined to avoid overworking the dough, which could make the cookies tough.
- Assemble cookies in muffin tin: Drop 2 tablespoons of the cookie dough into each muffin cup over the pineapple topping. Gently press the dough down to flatten slightly, ensuring it spreads evenly during baking for a uniform cookie shape.
- Bake the cookies: Place the muffin tin in the preheated oven and bake for 14 to 16 minutes, or until the cookies are golden brown around the edges and set in the center.
- Cool and invert: Allow the cookies to cool in the muffin tin for about 5 minutes to set. Then carefully invert the tin onto a cooling rack so the pineapple and cherry topping is displayed on top. This step releases the cookies without breaking the caramelized topping layer.
- Serve: Serve the pineapple upside-down cookies warm or at room temperature for the best flavor and texture. They make a perfect dessert or sweet snack.
Notes
- Ensure the crushed pineapple is very well drained to prevent soggy cookies.
- For best results, enjoy these cookies the same day they are made as the topping can become sticky over time.
- Store any leftovers in an airtight container at room temperature for up to 2 days.
- You can substitute maraschino cherries with fresh cherries or other fruit pieces if desired.
- Press the dough gently but firmly into the muffin cups to ensure even cooking and shape retention.
