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Rolo Cupcakes

These Rolo Cupcakes are the best chocolate cupcakes ever. I ran a cupcake bake sale for many years and let me tell you, this recipe was always a hit with kids and adults!

 

Main image for rolo cupcakes

 

Rich, fluffy, homemade chocolate cupcakes hide a gooey caramel center and are topped with a medium or dark chocolate frosting. Drizzle that with more caramel and place a Rolo on top. It is heavenly.

I absolutely love this caramel sauce. My father-in-law was literally licking the bowl. I think that is probably the best compliment I can get. But seriously, it’s AH-mazing.

These Rolo cupcakes are also super easy to make. While there are quite a few ingredients, it’s all so straightforward. No crazy directions here.

I add the caramel inside to the cupcakes AFTER they bake. Which means there is no chance the caramel will disperse and no longer be caramel filled. Which is way yummier, in my humble opinion.

Any excuse for me to go to the grocery store and buy more chocolate covered, caramel filled Rolos is a win. I love those sweet morsels.

 

cake mix added to cupcake liners, unbaked

 

Ingredients in Rolo Cupcakes

  • Chocolate Cake Mix: Any generic brand between 16-18 ounces will work. You’ll be dressing it up with all the other ingredients so don’t feel like you need to buy the most expensive brand.
  • Flour: I use all purpose, white flour. I do not recommend substituting with wheat flour. It’ll make the cupcake batter too heavy.
  • Sugar: The sugar is to sweeten up the generic cake mix. You need to make it your own. Use white, not brown sugar.
  • Salt: The salt is also for improving the boxed cake mix. 
  • Water: This is pretty standard for adding to cake mix.
  • Oil: Cupcakes made with oil tend to be lighter, fluffier, stay moist longer, and have more of an even crumb than cakes made with butter. I use vegetable oil, you could also use olive or avocado oil.
  • Vanilla: Use real vanilla extract, not imitation. The vanilla essence is totally worth it.
  • Sour Cream: Okay, here is probably where you are saying WHAT? Sour cream in cupcakes? Who does that? You do. And you’ll be glad you did.
  • Eggs: The eggs both hold your cake together and also help it to fluff it up.
  • Caramel Bits: You can buy caramel bits from the grocery store in the baking aisle, though they sometimes keep it in the candy aisle too. 
  • Heavy Cream: Not to be confused with whipped cream, which is already created for you, heavy whipping cream pours out of a container like milk, but much thicker and richer.
  • Butter: Take the butter out of the fridge before you start baking. It will allow the butter to come to room temperature and then you won’t have to wait for it. Unsalted butter or salted will work.
  • Cocoa Powder: The cocoa powder makes the frosting a medium to dark fudgy chocolate frosting. Which perfectly compliments the chocolate cupcakes.
  • Powdered Sugar: I don’t know whoever first thought of grinding up sugar granules but I’m glad they did. This may also be called confectioners sugar.
  • Rolos: You’ll want these unwrapped but don’t unwrap way ahead of time or little hands may eat them all. Or big hands. Maybe that’s just my house. I try to unwrap them right before I need them.

 

cupcakes fresh from the oven still in pan.

 

How to Make Chocolate Cupcakes

Making chocolate cupcakes with a gooey centre doesn’t need to be complicated.

  1. Amazing Cupcake Base: Chocolate cake mix, flour, sugar, salt, water, oil, vanilla, sour cream, and eggs all get blended to make the cupcakes.
  2. Caramel Syrup: For this you need the small pieces of caramel and heavy whipping cream. The center of each cupcake will get a drizzle.
  3. Icing Ingredients: Butter, cocoa powder, powdered sugar, and heavy whipping cream will create the caramel buttercream frosting. 

Pro Tips:

  • Use cupcake paper liners! It’ll save you so much cleaning up!
  • Don’t worry about the hole in the center of your cupcakes. Frosting covers it right up.
  • Microwave the homemade caramel sauce slowly in a microwave safe bowl and mix in between to prevent burning!
  • Use a piping bag to fill the middle of the cupcake with the tip of your choice.

 

caramel bits and cream in a microwave safe bowl, uncooked

 

How to Make Rolo Cupcakes

Does your homemade chocolate caramel Rolo cupcakes recipe feel more like a chocolate cupcake recipe and less like a Rolo cupcake recipe? Let’s fix that right up!

Before serving your delicious chocolate cupcakes, toss on an unwrapped Rolo candy. Your Rolo cupcake is complete!

Both the moist chocolate cupcakes and the Rolo are chocolate filled with caramel and your guests will love it.

Pro Tips:

  • Buy extra Rolo candies. Some of them always get eaten before they get on the cupcakes!
  • You could also use chunks of Rolo chocolate spread across the top of the cupcake.

 

caramel mixture cooked and smooth.

 

Can You Freeze Rolo Cupcakes?

These delicious cupcakes can be frozen at any point in the process. Always allow them to fully cool before freezing them. 

This Rolo cupcake recipe will last in the freezer for up to 1 month.

  1. Before Filling: This would probably be my chosen method to freeze them. Baked cupcakes can be wrapped tight to prevent freezer burn, and you can make the filling and whipped topping at the same time, toss it in the freezer, and let them all thaw overnight when you are ready to eat them.
  2. After Filling: This would be my second choice. Flash freezing would be the way to go here to prevent the caramel from sticking to the wrapping. Take them out after an hour, wrap them tight, and put them back in. Use when ready.
  3. With Topping: Once the whipped topping is on them, you can’t really wrap them up tightly or you will smash the tops of the frosted cupcakes But do make sure the container is airtight and they should still be fine.

Pro Tip:

  • Always cool cupcakes before placing in a freezer bag.
  • You can also use frozen Rolo or place the Rolo on the top of each cupcake once thawed.

 

zoomed out image of cupcakes on counter frosted and ready to eat.

 

Who Makes Rolos?

Rolos were first made in England by a man named John Mackintosh.(Thank you John Mackintosh! I’m a fan of Rolo!) 

Of course, today, they are made by a much more well known company. The Hershey Company!

You can find Rolos in almost any grocery store across the country.

Will a Chocolate Cupcake Hurt a Dog?

Yes! Dogs should not eat a chocolate cupcake. 

Sugar, wheat, and dairy products are all bad for dogs. 

But chocolate, especially in large doses, can actually be toxic.

To a small dog, even a small amount of chocolate can overwhelm their system. 

Be sure to keep all chocolate treats out of reach of your dogs to keep them safe.

 

cupcake cut in half to show caramel filling. Photo taken from the top looking down.

 

More Awesome Cupcakes You’ll Love…

Rolo Cupcakes, maybe you’ve heard of them, maybe you haven’t.

Either way, you are going to love them. Fluffy chocolate cupcakes, filled with the best caramel in the world, topped with a rich chocolate frosting, and decorated with a cute little Rolo. 

The ultimate indulgent treat for birthdays, parties, and any other event you can think of.

 

Yield: 24 Cupcakes

Rolo Cupcakes

cupcake cut in half to show caramel filling

These Rolo Cupcakes are the best chocolate cupcakes ever. I ran a cupcake bake sale for many years and let me tell you, this recipe was always a hit with kids and adults!

Prep Time 45 minutes
Cook Time 20 minutes
Total Time 1 hour 5 minutes

Ingredients

  • 1 (16 - 18 ounce) box of chocolate cake mix
  • 1 cup all-purpose flour
  • 1 cup white sugar
  • 3/4 teaspoon salt
  • 1 1/3 cup water
  • 2 Tablespoons vegetable oil
  • 1 teaspoon vanilla extract
  • 1 cup (8 ounces) sour cream
  • 2 eggs
  • 1 (11 ounce) bag of caramel bits
  • 1/4 cup heavy whipping cream, divided (this will be broken down into 2 sets of 2 Tablespoons)
  • 1 cup butter, room temperature
  • 1/2 cup unsweetened cocoa powder
  • 3 cups powdered sugar
  • 2 teaspoons vanilla extract
  • 2-4 Tablespoons of heavy whipping cream (use as much as you need to get to a creamy piping consistency)
  • 24 Rolos, wrappers removed.

Instructions

  1. Preheat oven to 325*F
  2. Line cupcake pans with cupcake liners.
  3. Blend cake mix, flour, sugar and salt.
  4. Slowly add water while the mixer is going. This is prevent clumps.
  5. Add vegetable oil, vanilla and sour cream. Mix well and scrape sides of bowl as needed.
  6. Add eggs one at a time.
  7. Scoop batter into cupcake liners using a cookie scoop - or filling them 2/3 full.
  8. Bake for 16 - 20 minutes until toothpick inserted into center comes out clean.
  9. Remove from oven and let rest in pan for 5 minutes then cool on cooling rack.
  10. Add caramel bits and 2 Tablespoons of heavy whipping cream to a microwave safe bowl.
  11. Microwave for 30 seconds, then remove and mix.
  12. Microwave for an additional 30 seconds if not melted and mix again.
  13. Add 2 more Tablespoons of heavy whipping cream to caramel to make it a smooth mixture that is running and not too thick. Set aside.
  14. In a new mixing bowl, blend butter until fluffy.
  15. Add cocoa powder and gently mix. Be careful not to breath in the cocoa dust.
  16. Once blended add powdered sugar 1 cup at a time, blending between each addition. Don't panic if you see little powdered sugar balls that you can't dissolve, the heavy whipping cream will take care of those.
  17. Add vanilla 2 Tablespoons of heavy whipping cream and blend well.
  18. Add 2 more Tablespoons of heavy whipping cream (or more 1 Tablespoon at a time) until mixture is of piping consistency.
  19. Pour caramel mixture into a piping bag with a metal tip.
  20. Stick metal tip into the center of each cupcake and gently squeeze a little caramel into each cupcake. Don't worry about the piping hole or if a little caramel gets on the top, you'll cover it with frosting.
  21. Place chocolate frosting into a piping bag with a tip and pipe frosting onto each cupcake, covering up the hole.
  22. Place an unwrapped Rolo on top of each cupcake for decoration.

Notes

Depending on how warm and humid your home is, will determine how soft your butter is.

Softer butter will need less whipped cream to thin out the frosting. Firmer butter will need more whipped cream to soften your frosting.

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Cupcakes can be frozen at any point. Before filling, after filling or with topping for up to 1 month. When ready to eat, remove from freezer and let thaw 1 hour before serving.

If you want to make your own caramel filling, I recommend this Caramel Sauce

Nutrition Information:

Yield:

24

Serving Size:

1

Amount Per Serving: Calories: 255Total Fat: 13gSaturated Fat: 7gTrans Fat: 0gUnsaturated Fat: 4gCholesterol: 44mgSodium: 162mgCarbohydrates: 33gFiber: 1gSugar: 27gProtein: 2g
Originally Posted: January 14, 2015

Photos & Text Updated: May 10, 2022

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Donna

Tuesday 30th of July 2024

Can I make the frosting and caramel the day before I bake the cupcakes

Num's The Word

Tuesday 6th of August 2024

Definitely!

Katie

Sunday 13th of February 2022

Hi! I made these sooo many times a couple of years ago. My coworkers loved them! Has something changed with the recipe? I feel like the dark chocolate pieces and buttermilk are missing and I don’t remember the cake mix. I just want to make sure I buy all of my ingredients tomorrow:). Thank you!

Martha Ann

Wednesday 15th of September 2021

I’ve seen some recipes where you place a Rolo in the middle of the batter before cooking. Do you think that method would work with this recipe to replace the caramel?

Janelle

Monday 11th of October 2021

You certainly can do that. I've found that the Rolo doesn't melt so it's just like finding a Rolo in the middle of your cupcake. In a pinch I've used caramel ice cream topping to put a Tablespoon in the center of each cupcake and that has worked great!

C.A.

Wednesday 24th of April 2019

Hi, have you tried freezing the cupcake with the caramel sauce in the middle so they only need the frosting when ready for use? I would put them in the refrigerator to defrost a couple days before frosting. Thanks for the recipe!

Janelle

Friday 26th of April 2019

Hi C.A. I've never frozen the cupcakes before. However it shouldn't affect the caramel. Right out of the freezer the caramel will be harder. However it should soften up if allowed to come to room temperature! Let me know how they turn out if you do try!

Brooke

Wednesday 25th of July 2018

Quick question on the caramel sauce and cupcakes. In the past I've used store bought caramel to fill my cupcakes and it seemed to just soak into the cupcakes. Of course I was making the cupcakes a day in advance. Will this caramel stay in the cupcakes as caramel filling or soak into the cake if I make it a day ahead? Thanks!

Janelle

Monday 6th of August 2018

When I make my homemade caramel sauce it stays in the cupcake. This is because it's more solid and thicker than the store bought stuff. Though I've had several people tell me that they like the soaked in caramel flavor.

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