Description
Pineapple Upside Down Cookies bring tropical sweetness right to your cookie plate, delivering a compact twist on the classic cake that fits perfectly in your hand. Caramelized pineapple and buttery dough combine for a delightful treat that sparks memories of family gatherings and summer desserts.
Ingredients
Scale
Topping Layer:
- 6 pineapple rings
- 6 maraschino cherries
- ½ cup unsalted butter, melted
- ½ cup light brown sugar
Wet Ingredients:
- 1 cup unsalted butter
- 2 large eggs
- ½ cup sour cream
- 1 tsp vanilla extract
Dry Ingredients:
- 3 cups all-purpose flour
- 1 cup granulated sugar
- ½ cup packed light brown sugar
- 1 tsp baking powder
- ½ tsp baking soda
- ¼ tsp salt
- 2 tsp cornstarch
Instructions
- Preheat your oven precisely to 350°F and coat a 12-cup muffin pan with cooking spray.
- Melt ½ cup unsalted butter and measure 1 teaspoon into each muffin cavity.
- Sprinkle 1 teaspoon light brown sugar over the melted butter in each cup.
- Cut pineapple rings into halves and place one half gently in the center of each cup.
- Position one maraschino cherry directly in the middle of each pineapple ring.
- Cream 1 cup room temperature butter with 1 cup granulated sugar and ½ cup brown sugar until smooth and fluffy.
- Incorporate 2 large eggs individually, mixing thoroughly after each addition.
- Blend in 1 teaspoon vanilla extract and ½ cup sour cream until completely combined.
- Whisk 3 cups all-purpose flour with 1 teaspoon baking powder, ½ teaspoon baking soda, ¼ teaspoon salt, and 2 teaspoons cornstarch.
- Gradually fold dry ingredients into wet mixture, creating a soft, consistent dough.
- Distribute cookie dough evenly over pineapple, filling each muffin cup about ¾ full.
- Bake at 350°F for exactly 20 minutes, checking for golden edges and set centers.
- Remove from oven and allow cookies to cool in pan for 10 minutes.
- Carefully invert muffin pan onto wire rack, letting cookies release naturally.
Notes
- Swap maraschino cherries with fresh cherries or a slice of candied ginger for a unique twist on the classic flavor.
- Use a silicone muffin pan for easier cookie removal and guaranteed no sticking.
- For a gluten-free version, replace wheat flour with a cup-for-cup gluten-free baking blend to maintain the soft, tender texture.
- Enhance the caramel notes by using dark brown sugar instead of light brown sugar, which deepens the rich butterscotch undertones.
- Prep Time: 15 minutes
- Cook Time: 18-22 minutes
- Category: Cookies
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 12
- Calories: 247 kcal
- Sugar: 16 g
- Sodium: 102 mg
- Fat: 13 g
- Saturated Fat: 7 g
- Unsaturated Fat: 6 g
- Trans Fat: 0.3 g
- Carbohydrates: 31 g
- Fiber: 1 g
- Protein: 2 g
- Cholesterol: 38 mg