I love making and eating desserts. Cliff, on the other hand is not a big sweets guy. I try to tempt him with all of the desserts that I make but he usually is not interested. It became my mission to find something that even he could not resist.
One thing he does enjoy is Rolos. We usually have a candy dish on our counter and the Rolos never last very long. So, in my mission to make a dessert he would crave, I decided it had to be a play on Rolos. We made these cupcakes a few weeks ago with this frosting and LOVED them, so I already knew what kind of cake and frosting I would make.
In order to make these even better (if that’s even possible) I decided to place a Rolo in each cupcake before we baked them. Once the cupcake is frosted, you won’t even know it’s there and the Rolo becomes a gooey surprise! Even Cliff found these irresistible!

Here's what you'll need

Mix dry ingredients

Cream butter and sugar

Add eggs

Add dry ingredients

Add milk

Fill cups three-quarters

Press Rolo into batter

Bake 10-13 minutes

Let cool

Pipe frosting

Cut Rolos in half

Place a half Rolo onto the frosting
Ingredients
For the Cupcakes:
¾ cup unsweetened cocoa powder
2 cups all-purpose flour
1 ¾ cups sugar
1 teaspoon baking powder
1 teaspoon baking soda
½ teaspoon salt
1 cup butter, softened
1 1/3 cups milk
2 eggs
2 teaspoons vanilla
1 bag of Rolos
For the Caramel Buttercream:
2 ½ cups light brown sugar
½ cup butter
1 cup heavy whipping cream, (put 2-3 tablespoons aside)
½ teaspoon baking soda
3-4 cups confectioners’ sugar
Note: For step-by-step frosting instructions, click here.
Directions
Makes 2 dozen standard cupcakes or 4-5 dozen minis
Preheat oven to 350 degrees F. Line cupcake pans with liners. In a medium bowl, combine flour, cocoa powder, baking powder, baking soda and salt; set aside. In the work bowl of a stand mixer fitted with a paddle attachment, cream butter and sugar on medium-high speed until light and fluffy, about 4 minutes.
Reduce speed to low, and add vanilla and eggs one at a time, scraping bowl after each addition. On low speed, alternately add flour mixture and milk. Start and end with the flour mixture, continue to mix until smooth.
Pour into prepared pans. Place 1 Rolo in each cup. Bake for 15-18 minutes or until a toothpick comes out clean (bake 10-13 minutes for minis). Let the cupcakes cool for 5-10 minutes then transfer to cooling racks to cool completely
To make the frosting, bring sugar and cream to a rolling boil using a medium sized heavy bottomed saucepan. Boil for one minute. Add baking soda, and boil another minute. Remove from heat. Add the butter but do not stir. Let the mixture cool in the fridge for 1-2 hours. As tempting as it is to stir make sure the mixture is completely cool first. It will look like a thick gummy caramel paste. Pour mixture into a stand mixer fitted with a paddle attachment, beat well. Gradually add powdered sugar alternately with 2-3 tablespoons of heavy cream. Beat for a few minutes until the consistency is creamy.
Pipe frosting onto cupcakes. Cut the extra Rolos in half and garnish each cupcake with half of a Rolo.
Source: adapted from Life in a Peanut Shell