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Rolo Cupcakes

Rolo Cupcakes

Are you a fan of Rolo’s?  If so you’ll love these Rolo Cupcakes!  When it comes to cupcakes here on Num’s the Word, Jodie is our resident cupcake expert.  She makes the best looking and tasting cupcakes around.  

For example, have you tried our Italian Cream Cheese Cupcakes or our Root Beer Float Cupcakes or our classic Vanilla Cupcakes.  In fact, right now on Nums, {Counting this post}, we have 15 cupcake recipes!  And all but this post, came from Jodie. See, I told you she was our cupcake gal.

So what does that mean?  It means, I’m more of a pie girl than a cupcake girl.  In fact, I don’t really care for cupcakes at all {GASP!}.  Yep.  You heard me.  {Shhh! Don’t tell Jodie!}

Ok but seriously, cupcakes just don’t do it for me.  And that is the real reason why I’ve never posted a caupcake recipe.  So for me to post about a cupcake, it has to be a BIG DEAL.  And let me tell you, this is a BIG DEAL.

For those two people who are still reading, I’m impressed!  Really you should leave a comment saying that you made it this far…because now comes the story behind WHY I even made cupcakes, because there has to be a good WHY to get me to make cupcakes.

A good family friend here in town was doing a bake sale to raise money to purchase requested supplies for a troop over seas.  I volunteered to bake multiple items and asked what she would prefer.  I was open to anything.

She requested cookies {of which I made these Snickerdoodle cookies}, muffins {recipe coming at a later date} and cupcakes.  I immediately thought to myself – GASP! Did she just say cupcakes?  I honestly tried to think of a legitimate reason to tell her cupcakes were just not going to happen, but then thought better of it.  I am a big girl and I could put on my big girl apron and figure out how to make a cupcake that wasn’t just edible, but freaking amazing.

And I did.

I found this recipe for Rolo Cupcakes.  They are off the charts, FREAKING AMAZING.  <– This coming from a girl who doesn’t like cupcakes.  Seriously, I have now made them SEVERAL times in the last few months and they turn out great EVERY time.  SOOOOOO good. 

Moist chocolate cupcakes with a gooey caramel center {BEST CARAMEL EVER!} then topped with a medium to dark chocolate frosting, drizzled in more caramel sauce with a Rolo on top.  

If that didn’t get your attention, then really, what will?  These are by far the most amazing cupcake I’ve ever had and will be the best you ever have too!  Did I mention they were the bomb diggity?  As in I caught my Father in Law scraping the pan with a spoon trying to get every last ounce of caramel from the pan, or how I can’t stop making them!  Yea.  Try them.  AHHHMAZING!

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Rolo Cupcakes 2
Rolo Cupcakes 3
Rolo Cupcakes

Prep Time: 45 minutes

Cook Time: 20 minutes

Total Time: 1 hour, 5 minutes

Yield: 12 Cupcakes


  • ----------------------------
  • 1/2 cup butter, at room temperature {I use salted}
  • 1 cup white sugar
  • 2 eggs
  • 2 teaspoons vanilla
  • 3/4 cup buttermilk
  • 1 cup all-purpose flour
  • 1/2 cup cocoa powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon baking powder
  • 1 pinch of salt
  • 1 ounce dark chocolate, finely chopped
  • ----------------------------
  • ----------------------------
  • 1 C. white sugar
  • 6 Tbsp. butter, room temperature {I use salted}
  • 1/3 C. heavy cream
  • ----------------------------
  • 1 C. butter, softened {I use salted}
  • 3/4 C. unsweetened cocoa powder
  • 2-3 Tbsp. milk
  • 2 tsp. vanilla extract
  • 3-4 C. powdered sugar
  • 12 Rolos for garnish


  2. ----------------------------
  3. Preheat oven to 350*F
  4. Line cupcake pans with cupcake liners
  5. Using a stand mixer, beat the butter and sugar until fluffy, scraping down sides as needed.
  6. Add eggs, mixing one at a time until well blended.
  7. Add vanilla, mixing well, scraping sides of bowl down as needed.
  8. While mixer is on, slowly add buttermilk.
  9. Add salt, baking powder, baking soda and cocoa powder. Mix until well incorporated.
  10. Add flour & chopped chocolate, mix until batter is smooth.
  11. Fill each liner 2/3 full with cake mix.
  12. Bake for 18 - 22 minutes until a toothpick inserted in center of cupcake comes out clean
  13. ----------------------------
  15. ----------------------------
  16. In a medium heavy sauce pan over medium-high heat, add sugar to pan. DO NOT ADD ANYTHING ELSE! TRUST ME!
  17. DO NOT LEAVE THE STOVE! Slowly whisk the sugar until it melts and turns into a dark amber color. If it is chunky at first, don't panic. It will eventually be smooth and runny.
  18. Once sugar is melted and a nice dark amber color, and while heat is still on, immediately add the butter and whisk quickly until it is melted.
  19. Once butter is melted, remove from heat.
  20. Continue whisking as you add the cream.
  21. Once full incorporated, set aside and let cool - This may take an hour or so. I prefer to make mine the night before and let it cool overnight on the stove.
  22. When cool and ready to use, hollow out the center of each cupcake, reserving the top, Fill cupcake with caramel.
  23. Replace top numb of cupcake over the caramel.
  24. ----------------------------
  26. ----------------------------
  27. Using a hand or stand mixer, beat butter until fluffy, about 2 minutes.
  28. Add cocoa, 2 Tablespoons milk and vanilla extract. Mix until smooth and incorporated.
  29. Add in powered sugar 1/2 cup at a time, until you reach your desired consistency, add remaining Tablespoon of milk if needed.
  30. Using a piping bag or a ziploc bag with tip cut off, frost cupcakes.
  31. Drizzle remaining caramel sauce on top of frosting.
  32. Top with a single unwrapped Rolo candy.

Recipe discovered from Cupcakes & Homeschooling


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8 thoughts on “Rolo Cupcakes

  1. Holy cow! Stumbled across this post while in search of a yummy filling for my cupcakes. This sauce is currently in my saucepan and has completely thickened and we have “sampled” it again and again with chunks of the chocolate cake were supposed to be using. It’s so, so good! And so, so easy! Thanks a bunch! Gonna quadruple recipe now.

    • Vero, you are I are of the same mind when it comes to that caramel. I caught my Father-in-Law practically licking the pan clean when I was done with it. Just think of the possibilities you can make with this caramel sauce – ice cream topping, cakes, pies (caramel apple pie anyone?!) I feel like I’m gaining weight just thinking of all the ways. I’m so glad to hear you love it as much as we do! Thank you so much for your review, you’ve made my day!

  2. Made these for my daughters water polo team and WOW! They loved them!
    I went messy thick with the caramel so we needed forks to eat them.
    Sooo good!

    • Rob….welcome to the gooey side! Oh man I don’t see anything wrong with messy thick. That caramel sauce is incredible!! So glad everyone loved them! Thank you for taking the time to leave your review, you’ve just made my day!

    • Hi Melissa! The recipe is pretty flexible on your chocolate choice. I generally use what I have on hand. I personally love Lintz or Ghiradelli. I’ll nab a tasty bar of it and then break off 1 ounce for the cupcakes. A lower quality of chocolate can be used or chopped up chocolate chips but they don’t melt as well when baking. I hope you love these! Be warned though, the caramel is Ah-MAZING!

    • Hi Jaimee! That is a very good question. I’ll update the recipe to reflect that it’s WHITE sugar. 🙂 Give it a try and watch the magic happen. Or cheat and go buy some caramel sauce from the grocery store (though it wont taste as good)! Thanks for the comment!

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