Rolo Cupcakes with Caramel Frosting

With a little bit of a switcheroo in using a cake mix, you can have yourself a bakery style cupcake with all the trimmings in no time. This is one of our favorite cupcakes. Enjoy! This recipe can also be adapted to make PB Cupcakes.


  • 1 package chocolate cake mix (I like using triple fudge :))
  • 1 – 5.9 oz. package instant chocolate pudding mix
  • 1 cup sour cream
  • 1 cup vegetable oil
  • 4 whole eggs (lightly beaten)
  • 1/2 cup warm water
  • 1 teaspoon vanilla
  • 24 rolos (unwrapped and frozen for at least two hours)


  • 2 cups butter (room temperature)
  • 2 teaspoon vanilla
  • 1/4 teaspoon fine sea salt
  • 1/3 cup caramel syrup ((or use peanut butter for PB Cups))
  • 1 – 1/2 pounds powdered sugar


  • 4 ounce bittersweet chocolate (chopped into very small pieces (I have also used semi-sweet chocolate chips))
  • 1/2 cup heavy whipping cream
  • 2 Tablespoon corn syrup
  • 2 teaspoon vanilla

To Make Cupcakes:

  1. Preheat oven to 350 degrees. Line 24 muffin tins. (I like the Reynolds tinfoil ones. I have also recently started using the name brand Wilton and like those.) . Sift cake mix into mixing bowl. In a separate bowl, add all other ingredients, except the frozen rolos. Gradually add to cake mix. Using a large cookie scoop (3 Tablespoon), scoop one into each muffin tin. Bake cupcakes for about 10 minutes and then press the frozen rolo (or can also use a PB cup) in center of cupcake. Finish baking for an additional 8-10 minutes more. Cool Completely.

To Make Frosting:

  1. Cream the butter in the bowl of an electric mixer. Add the vanilla extract, salt and caramel syrup and combine well. Begin adding in the sugar and mixing thoroughly after each addition. After all of the sugar has been added and mixed thoroughly, taste to see if you want more caramel flavoring. Pipe onto cooled cupcakes.


  1. In a small saucepan over medium heat, warm the heavy cream until very hot, but not boiling. Stir constantly. Turn off heat. Slowly add the chocolate pieces. Let melt. Whisk the mixture until smooth. Whisk in the corn syrup and vanilla. Allow to cool slightly. Put in a squeeze bottle. Squeeze a bit on the top of our frosting and top with a Rolo (or PB cup if making PB). Store in fridge. Take out one hour before serving.

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