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Rolo Stuffed Chocolate Chip Cookies – An Indulgent Snack

I’ve just got to get this out of my system.

Ever since I saw these Oreo Stuffed Chocolate Chip Cookies over at Picky Palate, I’ve been wanting to try something similar. I have a little thing for chocolate chip cookies. And by little, I mean big. And by big, I mean huge. And by huge, I mean…

You get the picture.

After making these, I’m really not sure that chocolate chip cookies will ever be the same again. I am not sure I’ll ever be able to make unstuffed cookies again!

The key with these…

You have to let them cool to just the right temperature.  Still a bit warm, but cool enough for the caramel to have started to harden.  But only just a little bit.

And if you get it at just the right time, you take a bite…and as you pull the cookie away, a long string of caramel forms and you have to catch it!

It’s a moment of ooey, gooey stuffed cookie perfection.

I sure hope you can recreate that moment!

Rolo Stuffed Chocolate Chip Cookies

Inspired by Oreo Stuffed Chocolate Chip Cookies


  • 2 1/2 cups flour
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1 cup butter or margarine
  • 3/4 cup sugar
  • 3/4 cup brown sugar
  • 1 tsp vanilla (or use homemade vanilla extract!)
  • 2 eggs
  • 2 cups chocolate chips
  • Enough Rolos for each cookie, about 18


  • In a mixing bowl, whisk together the flour, baking soda and salt.
  • In a stand mixer or mixing bowl, beat together the butter/margarine and the 2 sugars. Add in the vanilla. Beat in the eggs, 1 at a time, until smooth. Scrape down the sides if necessary.
  • Add the dry ingredients and mix on low speed, until batter forms.
  • Fold in the chocolate chips.
  • Flatten the Rolos, using a potato masher, or the bottom of a measuring cup.
  • Form the cookies by placing dough on top and on bottom of the flattened Rolos. Place on cookie sheet, or Silpat baking mat, and bake at 350 for 9-11 minutes, or until begin to golden.
  • Let cool slightly before serving. Makes 18-24, depending on how much dough you use for each cookie.