I absolutely love Rolos. There’s just something fantabulous about delicious caramel coated in chocolate that is irresistible to me. So one day at work, I was talking to people trying to figure out what kind of cupcake I should try next and someone originally suggested a Reese’s style cupcake. Big problem though: I hate peanut butter. So I thought about other chocolate candies that were filled with something (I needed to do something chocolate) and Rolos were my first thought. Everyone else thought it was a fantastic idea. Thus the Rolo cupcake was born. I didn’t actually make my own caramel to fill the cupcakes because I’m not that adventurous and after watching my roommate make caramel for brownies once I decided that I just didn’t want to deal with it. But they were still delicious. I used the recipe for the cake part of Better than Sex cupcakes to ensure that the cupcake was rich and chocolatey. For the frosting, I did a standard vanilla buttercream, but I also added just a little bit of cocoa powder to tint it and give it that little extra bit of oomph. These cupcakes could also go without frosting to really capture the flavors of the candy. In true Rolo style, I used gold foil papers, which really grabbed the attention of my lovely crew of taste testers over at Jimmy John’s. Overall, this cupcake is simple, yet definitely a crowd pleaser!
Makes approximately 16 cupcakes
For the cupcakes:
1/2 cup (1 stick) butter, room temperature
1 1/4 cups sugar
2 large eggs, room temperature
3/4 cup flour
1/2 teaspoon baking powder
1/4 teaspoon baking soda
1/4 teaspoon salt
1/2 cup unsweetened cocoa powder (I just used Hershey’s cocoa powder because I already had it)
1/2 cup milk
1 teaspoon vanilla
2/3 cup mini chocolate chips (optional)
Preheat oven to 350 F. Beat butter until softened. Add sugar and beat until light and fluffy. Add eggs, one at a time, beating until well combined. Mix flour, baking powder, baking soda, salt, and cocoa powder in a small bowl. Mix milk and vanilla in a separate bowl. Add about 1/3 of the dry ingredients to the butter/sugar/egg mixture and beat to combine. Add about half of the milk/vanilla and beat to combine. Continue adding, alternating between dry and wet, finishing with the dry ingredients. Stir in chocolate chips, if using. Scoop batter into cupcake cups about 1/2 full. Bake for 22-25 minutes or until a cake tester comes out clean. Allow cupcakes to cool completely before filling/frosting.
For the Filling:
Caramel sauce of your choice (needs to be fairly gooey, not solid. I used Hershey’s)
Once cupcakes are completely cooled, fill a small squeeze bottle with caramel and insert the tip into each cupcake, squeezing caramel into the cake until it starts to ooze out of the top. Be careful not to overfill.
For the Frosting:
3 cups powdered sugar
1/3 cup butter or margarine, room temperature
1 1/2 teaspoons vanilla
1 to 2 tablespoons milk
About 1 tablespoon cocoa powder (used to tint, not to flavor)
Mix the powdered sugar and butter until well mixed. Stir in vanilla and 1 tablespoon of milk. Gradually beat in just enough of the remaining milk to achieve desired thickness. Add in cocoa powder as necessary, until frosting is lightly colored and has no distinct chocolate flavor (unless that’s what you want, of course).
Pipe (or spread) frosting onto cupcakes using whatever tip you want, I used Ateco tip #809. If desired, drizzle remaining caramel over cupcakes.