Description
Looking for a fun twist on a classic treat? Try making Pineapple Upside Down Sugar Cookies today! Discover a delicious new recipe.
Ingredients
Scale
- 4 tablespoons unsalted butter
- 3/4 cup brown sugar, packed
- 1 can pineapple rings, drained (reserve 2 tablespoons juice)
- 12–15 maraschino cherries, halved
- 2 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/2 teaspoon salt
- 3/4 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg, room temperature
- 1 teaspoon vanilla extract
- 2 tablespoons reserved pineapple juice
- 1/4 teaspoon almond extract (optional, enhances flavor)
Instructions
- Step 1: Prepare Your Baking Sheets Preheat your oven to 350°F (175°C). Line two muffin tins or baking sheets with parchment paper if using regular cookie sheets. If using muffin tins, lightly grease each cup with cooking spray. The individual wells of a muffin tin help contain the caramel topping beautifully, but regular baking sheets work well too.
- Step 2: Create the Caramel Base In a small saucepan, melt butter over medium heat. Add brown sugar and stir constantly until the mixture becomes smooth and begins to bubble slightly, about 3 minutes. Remove from heat and let cool for 5 minutes. If using muffin tins, spoon about 1 tablespoon of the mixture into each cup. If using baking sheets, drop tablespoon-sized portions about 3 inches apart.
- Step 3: Add Pineapple and Cherries Cut pineapple rings into quarters (or smaller if needed). Place one piece of pineapple onto each caramel portion, pressing gently. Add half a maraschino cherry beside each pineapple piece, pressing slightly into the caramel. The arrangement might seem small, but remember the cookie dough will spread around it.
- Step 4: Prepare the Cookie Dough In a medium bowl, whisk together flour, baking powder, and salt. In a separate large bowl, beat softened butter and granulated sugar until light and fluffy, about 3 minutes. Add egg, vanilla extract, pineapple juice, and almond extract if using. Mix until well combined. Gradually add the dry ingredients to the wet ingredients, mixing just until incorporated.
- Step 5: Form and Bake the Cookies Using a cookie scoop or spoon, drop about 2 tablespoons of dough over each pineapple-topped caramel portion. Gently press the dough to flatten slightly, but don’t press all the way to the edges—the dough will spread during baking. Bake for 12-15 minutes until the cookies are just turning golden at the edges but still soft in the center.
- Step 6: The Dramatic Flip Allow cookies to cool in the pan for exactly 5 minutes. Run a knife around the edge of each cookie to loosen. Place a cooling rack or serving plate over the pan and, using oven mitts, carefully flip the entire pan in one swift motion. Leave the pan in place for 30 seconds to allow the caramel to drip down onto the cookies, then gently lift it off. Let the Pineapple Upside Down Sugar Cookies cool completely before serving.
Notes
Fresh ingredients will always yield the best flavor results.
Nutrition
- Serving Size: 1 serving
- Calories: 300
- Sugar: 5g
- Sodium: 400mg
- Fat: 10g
- Saturated Fat: 3g
- Unsaturated Fat: 7g
- Trans Fat: 0g
- Carbohydrates: 40g
- Fiber: 5g
- Protein: 15g
- Cholesterol: 50mg