Werther’s Original
Caramel Pineapple Upside-Down Cupcakes

Caramel Pineapple Upside-Down Cupcakes

Try our version of the nostalgic classic! Our Pineapple Upside-Down Cupcakes feature a golden brown caramel glazed pineapple made with Werther’s Original Chewy Caramels.


Intermediate Difficulty


  • 22 (5 ounces) Werther’s Original Chewy Caramels, unwrapped
  • 12 slices of canned pineapple, drained
  • 12 maraschino cherries, drained
  • 3 large eggs, room temperature
  • 2 cups sugar
  • 1 cup vegetable oil
  • 1 cup sour cream
  • 2 teaspoons pure vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon kosher salt
  • Whipped topping, for serving


  1. Preheat oven to 350°F. Line a 12-cup jumbo muffin tin with parchment paper squares. Grease each cup lightly with cooking spray.

  2. Place a pineapple slice and cherry in the bottom of each muffin cup. Beat eggs and sugar in a large bowl with a whisk or electric hand mixer until thick and pale yellow, about 3 minutes. Beat in oil, sour cream and vanilla until smooth. Whisk together flour, baking powder, baking soda and salt in a separate small bowl. Slowly add dry ingredients to egg mixture until combined. Fill each muffin cup 2/3 of the way with batter.

  3. Bake until toothpick inserted comes out clean, about 30 to 35 minutes. Cool for 5 minutes. Transfer cakes to a wire rack to cool completely.

  4. Meanwhile, combine caramels and water in a microwave-safe bowl. Microwave mixture in 30-second increments, stirring between each increment, until caramels begin to melt, about 1 to 1 1/2 minutes. Remove parchment paper and invert cakes. Serve with a drizzle of caramel sauce and whipped cream.

  5. Makes: approx. 12 servings/pieces

    Prep Time: 10 minutes

    Cook Time: 45 minutes

    Ready in: 55 minutes