Caramel Stuffed Chocolate Chunk Cookies

These rolo-stuffed chocolate chip cookies are irresistible!  You’ll love your chocolate chip cookies stuffed with rolos.

Caramel Stuffed Chocolate Chunk Cookies from JensFavoriteCookies.comMy niece recently broke her elbow.  This is particularly bad because she is a serious basketball player, and this put a serious cramp in her serious-basketball-player summer plans.

She is also the tallest 8th grader I have ever known, and maybe the sweetest.

Continuing with my new trend of making a batch of cookies for my nieces and nephews on their birthdays (remember this one?  and this one?), I asked World’s Tallest Niece what flavor combo she was looking for.  The problem is, she is far too kind to commit to one flavor.  

I think she believes the peanut butter will feel bad if she chooses caramel.  Not exaggerating.

It’s lucky The Hippie Chick and World’s Tallest Niece are BFF’s, so I can get the inside scoop about which flavors she actually prefers.

Caramel Stuffed Chocolate Chunk Cookies from

Hippie Chick confided that World’s Tallest Niece had been craving Rolo’s, and they even walked to the store with their hard-earned cash to procure some.

I had been wanting to make some caramel-stuffed cookies anyway, and after this story, I decided to use Rolo candies instead of caramels to stuff the cookies.

Turns out, I’m brilliant.  (And humble.)

Caramel Stuffed Chocolate Chunk Cookies from JensFavoriteCookies.comCaramel Stuffed Chocolate Chunk Cookies from

A word or two about this recipe.  Don’t skip the chilling step.  It’s uber-important.  And leave plenty of room for these very large cookies to spread.

Can you stuff them with caramels?  Sure.  Peanut butter cups?  Sure.  Nothing at all?  Absolutely.  Make them your own, my friends.

I did find that even when they were pretty well sealed up, the caramel still found a way to leak out of the bottom of the cookie, so be prepared with some paper towels, to save yourself some elbow grease.

These won’t cure cancer, or broken elbows, but they are the next best thing.  Happy Birthday, World’s Tallest Niece.

Want more?  Here are more great chocolate chip cookies!

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5.0 from 1 reviews
Caramel Stuffed Chocolate Chunk Cookies
Cook time
Total time
A brown butter cookie with chunks of bittersweet chocolate, stuffed with caramel Rolo candies.
Recipe type: Cookies
Serves: 21
  • 1 cup butter
  • 1 cup brown sugar
  • ½ cup sugar
  • 1 egg + 1 egg yolk
  • 1 teaspoon vanilla
  • ½ teaspoon salt
  • 1 teaspoon baking soda
  • 2¼ cups flour
  • 4 oz. bittersweet chocolate
  • about 20-25 Rolo candies
  1. Melt ½ cup butter in a saucepan. Continue cooking, stirring occasionally, until butter browns. Meanwhile, cut remaining ½ cup butter into small pieces and place in a mixing bowl. As soon as melted butter is brown, pour it over the butter pieces in the mixing bowl. Let sit, stirring occasionally, until butter is melted.
  2. Add sugar and brown sugar, and mix well. Add vanilla and eggs and mix well. Add salt and soda and mix well.
  3. Add flour and mix just until combined. Roughly chop the chocolate, and mix it gently into the dough.
  4. Unwrap Rolo candies, and create a ball of dough with one candy inside. Ensure that dough is sealed tightly around the Rolo. Cookies will be large. Place cookies on a baking sheet or plate, and chill for about 1 hour.
  5. Bake chilled cookies at 350F for 11-15 minutes, until edges are lightly brown. Let cool before serving. (*Note that caramel from the candy may leak out the bottom of the cookie, so you may want to put a lining under the cooling rack.)


5 thoughts on “Caramel Stuffed Chocolate Chunk Cookies

  1. Nancy @ gottagetbaked

    I love baking with Rolos – it does something magical to the caramel and makes it so buttery, chewy and flavourful. These cookies are gorgeous. The cracks on the surface are perfect and they look so dense ‘n chewy (my fave cookie texture). I hope the world’s tallest niece enjoyed every bite!

  2. Pingback: 100 Chocolate Chip Cookie Recipes |

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