Rolo Cupcakes

Rolo Cupcake

The Story:

There are fraternal twins in the candy world.

Chocolate and Caramel got married and had the Rolo and the Milk Dud.  They both have milk chocolate outsides with caramel insides, but one is soft and gooey and they other loves to latch on to your teeth during the movie and distract you from Brad Pitt’s face.  The latter also loves to make a lot of noise dancing around in the box during the movie so you get “shush’d” by the old people in front of you! The Milk Dud is the troublemaker child.

Maybe I think about candy too much…[end-story]

Rolo Cupcakes


Chocolate Cake:
1 Box Devil's Food or Chocolate Cake Mix
3 eggs
1/2 C. oil
1 C. buttermilk or milk
1/2 C. sour cream
2 tsp. vanilla extract
Caramel Filling:
1 C. sugar
6 Tbsp. butter, room temperature
1/3 C. heavy cream
Chocolate Frosting:
1 C. butter, softened
3/4 C. unsweetened cocoa powder
2-3 Tbsp. milk
2 tsp. vanilla extract
3-4 C. powdered sugar
Rolos for decoration


1. Preheat oven to 350 degrees and line pans with cupcake liners.
2. Sift cake mix into a small bowl and set aside.
3. In a large bowl, combine eggs, oil, buttermilk, sour cream and vanilla extract.
4. Add cake mix and stir until smooth.
5. Fill cupcake liners 3/4 full and bake for 17-22 minutes or until an inserted knife comes out clean.
6. Filling: In a sauce pan over medium-high heat, whisk the sugar until it turns into a dark amber color. Immediately add the butter and whisk quickly until it is melted. Once melted, remove from heat. Then whisk while adding your cream. Let cool.
7. Chocolate Frosting: Beat butter for 2 minutes. Add cocoa, 2 Tbsp. milk and vanilla extract. Beat again. Slowly add in powered sugar until you reach your desired consistency, add more milk of needed.
8. To assemble, cut little holes out of the tops of your cooled cupcakes, fill with caramel, cover the hole with buttercream, drizzle extra caramel over the top and finish with a Rolo.


Feel free to use store bought caramel. No shame in that.

Rolo Cupcakes

22 thoughts on “Rolo Cupcakes

  1. 1
    Jennifer says:

    There’s no such thing as thinking about candy too much. Love your site!

  2. 2
    Amanda says:

    I was looking through your site for a cupcake recipe to make and started looking through Easter candy I could find a cupcake recipe with. I saw we had a lot of Rolos so as I was about to search your site for “Rolos” I saw a new email on my phone that you had just posted one! So weird. I’m definitely trying this today! Thanks!

  3. 3
    Heather says:

    I love Rolos. They look yummy!

  4. 4
    Nancee says:

    YUM!!! I love Rolos. And you can bet that as soon as I get these braces off my teeth in about 4 months I’m sitting down with a bag. I may just make these cupcakes too. 🙂

  5. 5
    Tieghan says:

    Looks so good!

  6. 6
    Kristy says:

    My son loves Rolos! So going to have to make these!

  7. 7
    Anonymous says:

    Hey, you’re from Portland right? Have you ever been to or heard of Cupcake Jones?? 🙂

  8. 8

    Hi I am going to make these cupcakes for my daughter’s birthday! How many cupcakes does this recipe make?

  9. 9
    Samantha says:

    What tip did you use? I’m going to make these for my students for Kids Day. Thanks!! Can’t wait to make them.

  10. 10
    Katie says:

    Wait, so can you use store bought caramel for the filling?


  11. 11
    Clare says:

    I made these, they came out beautiful, I’m sure they will taste as good as they look. My caramel soaked into the cake before I was able to frost them. Like I said….they’re going to be YUMMY!!
    Thanks for sharing!

  12. 12
    Emily says:

    I just made these for my son’s birthday 3rd birthday party yesterday but replaced the rolo with a Hershey’s golden nugget to stay with our pirate theme. They were scrumptious and everyone raved about them. This was my first time to make something from your website and I too was leery about using a boxed cake mix, but no one knew and it saved a bunch of time! Really, I didn’t think I could make cupcakes that would be that good! Thank you so much for the recipe!

  13. 13
    Laura says:

    I have become your representative of cupcake-making in my office. I am making these next week and I have wondered if the caramel will melt into the cake of the cupcake?

  14. 14
    Mel says:

    I don’t like using cake mixes, so what kind of cake recipe is equivalent to what you’ve used?

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