Description
These Pineapple Upside Down Cookies are a delightful twist on the classic dessert, combining moist and buttery cookie dough with caramelized pineapple rings and maraschino cherries. Baked in a muffin tin, each cookie features a golden-brown crust with a sweet, sticky pineapple topping, perfect for a simple yet impressive treat.
Ingredients
Cookie Dough
- ½ cup Butter, softened
- ½ cup Granulated Sugar (100g)
- 1 Large Egg
- 1 teaspoon Vanilla Extract
- ½ cup Powdered Sugar (65g)
- ¼ cup Vegetable Oil
- ½ teaspoon Baking Soda
- ½ teaspoon Cream of Tartar
- 2 cups All Purpose Flour (240g)
Topping
- Pineapple Rings, drained
- Maraschino Cherries, drained
- 6 tablespoons Butter, melted
- 1 cup Brown Sugar (214g)
Instructions
- Pan Preparations: Preheat your oven to 350°F. In a small bowl, combine 6 tablespoons of melted butter with 1 cup of brown sugar, mixing until smooth.
- Arrange Toppings: Drain pineapple rings thoroughly. Place 1 tablespoon of the brown sugar and butter mixture into each well of a muffin tin. Top each with one pineapple ring, then place a maraschino cherry in the center of each pineapple ring. Arrange the wells staggered to give cookies space to spread.
- Prepare Cookie Dough: In a mixing bowl, cream softened butter and granulated sugar together until light and fluffy, scraping down the bowl as necessary. Add the egg and vanilla extract and continue to cream for 2-3 minutes until well combined and airy.
- Add Additional Wet Ingredients: Gradually add vegetable oil and powdered sugar to the creamed mixture, mixing until the mixture turns pale yellow and smooth.
- Combine Dry Ingredients: In a separate bowl, whisk together all-purpose flour, baking soda, and cream of tartar. Gradually add these dry ingredients to the wet mixture, stirring until just combined.
- Shape and Assemble Cookies: Using a #24 cookie scoop, portion the dough. Flatten each dough ball in the palm of your hand to about 3 inches in diameter. Place each flattened dough piece on top of the pineapple ring and cherry in each muffin well. Gently press the dough down and tuck neatly into the edges of the well to seal.
- Bake: Bake in the preheated oven for 8-10 minutes, or until the edges are lightly golden and the center loses its glossy appearance.
- Cool and Flip: Remove the muffin pan from the oven. While still warm, carefully invert the pan onto a parchment-lined baking sheet. The cookies will gently release from the wells, revealing the iconic upside-down pineapple topping.
- Serve: Allow cookies to cool completely before serving to ensure the topping sets and the cookies maintain their shape.
Notes
- Ensure pineapple rings are well drained to prevent soggy cookies.
- Stagger muffin placement on the baking sheet to allow for even baking and spreading without sticking.
- Use a cookie scoop for uniform cookie size and baking consistency.
- Flipping the pan immediately after baking helps retain the sticky topping on the cookie surface.
- These cookies are best enjoyed fresh but can be stored in an airtight container for up to 3 days.
- Prep Time: 12 minutes
- Cook Time: 10 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
