Rolo Surprise Cookies

Chocolate and caramel are a wonderful combination, possibly only matched by chocolate and peanut butter. Some of the most popular candy bars feature this combination, like Caramilk, Twix, Mars, Snickers and Rolo just to name a few. We often have a package or two of Rolo in the house and I decided it was time to incorporate them into some baking. I put the Rolo candies in the freezer and made some nice chocolate cookie dough which would be nice and fudgy. I often make cookies that I roll in a ball and toss in some sugar. I find them to have the perfect shape and I decided to stuff a Rolo candy in each one to create a nice little surprise when bitten into.

In the end, these cookies were even better than I thought they would be. They are rich and chocolately and a perfect addition to this years 24 Days of Christmas Baking! This recipe is slightly adapted from Two Peas and Their Pod.

Rolo Surprise Cookies

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Prep Time: 20 minutes
Cook Time: 15 minutes
Total Time: 35 minutes
Servings: 35


  • 1 cup butter , softened
  • 1 cup brown sugar
  • 1 cup white sugar
  • 2 eggs
  • 2 tbsp milk
  • 1 tsp vanilla
  • 1 cup cocoa powder
  • 2 1/2 cups flour
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1/4 cup white sugar (for rolling)
  • 4 packages of Rolo's (approx. 40 Rolo candies)


  • Place the Rolo candies in the freezer about an hour before preparing the cookies.
  • Using an electric mixer, cream together the butter, both sugars, eggs, milk and vanilla until smooth.
  • In a separate bowl, whisk together the cocoa powder, flour, baking soda and salt. Beat the flour into the wet mixture slowly.
  • Take out just enough Rolo candies, from the freezer, for each batch of cookies.
  • Take one spoonful of cookie dough and one Rolo candy. Cover the Rolo candy with the cookie dough, ensuring that the candy is totally surrounded in the dough. Roll the dough in your hands to create a ball. Then gently roll the ball of dough in the 1/4 cup of white sugar. Place on a cookie sheet lined with parchment paper.
  • Place the cookie dough balls 2 inches apart on the cookie sheet.
  • Bake in a 350F oven for 12-15 minutes.
  • Cool on a wire rack.



Did you try this recipe?

Leave a comment and let me know how it turned out. Or, take a picture to share on Instagram and tag me @theblackpeppercorn.

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  • One whole cup of cocoa? This isn’t a typo?
    Just want to be sure.

    • Reply
    • Yep – one whole cup. Makes it nice and fudgy!

      • Reply
  • hi! I want to ask, what is rolo’s? it doesn’t look available in my country… i live in Indonesia… so what can replace it?

    • Reply
    • Rolo is a bite size chocolate candy with a caramel filling. Anything similar should work ok

      • Reply
  • Works, Stevie Wonder…and these are divine!!

    • Reply
  • Hi Steve,
    I have a question…when you say “brown sugar”, do you mean dark brown sugar or golden yellow sugar? This is an on-going thing with my sister and Mother (in my Mother’s recipes, she always uses the golden yellow sugar and my sister uses dark brown). 🙂
    Thanks, Kathy

    • Reply
    • Hey Kathy! I typically mean the light brown sugar (golden yellow), unless I specify dark brown. Either way, in a recipe like this, you likely would not notice much difference between the two. The dark just has a bit more molasses in it. Hope that helps.

      Say hi to Rocco!

      • Reply

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