Chocolate Chip Rolo Cookies

Chocolate chip Rolo cookies feature a soft, chewy chocolate chip cookie filled with an ooey, gooey Rolo center. These Rolo cookies will make you rethink the classic recipe!

Chocolate Chip Rolo Cookies

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I have a thing for Rolos, and by thing I mean I like to put them in every dessert I possibly can. I’ve made salted caramel Rolo cookies and candy-coated Rolo pretzel pumpkins.

Chocolate Chip Rolo Cookies

Chocolate chip Rolo cookies are just another excuse to eat Rolo candies—not that I need an excuse, mind you. But I can always use an excuse to bake a batch of homemade cookies.

Chocolate chip cookies filled with those caramel-filled bundles of goodness? Heck to the yes.

Chocolate Chip Rolo Cookies

Before you start questioning the tastiness of this Rolo cookie recipe compared with your classic Rolo cookies, let me tell you a little bit about these cookies.

You have my favorite cookie dough recipe, which I use for all my pudding cookies, and you have Rolos. It’s basically a match made in heaven!

Chocolate Chip Rolo Cookies

Speaking of a match made in heaven, have you baked my salted caramel bars yet? Or made this easy chocolate chip brownie cheesecakes? They’re absolutely heavenly!

Chocolate Chip Rolo Cookies

If you want to bake the ideal chocolate chip Rolo cookies, I highly recommend parchment paper (I love this pre-cut baking sheet parchment paper) or a silicone mat (this set is awesome!).

And of course, I never bake a batch of cookies—unless it’s peanut butter no-bake cookies—without my must have kitchen gadget, the cookie dough scoop!

Chocolate Chip Rolo Cookies

That cookie dough scoop makes perfectly sized cookies every time! It also makes it easier to wrap the cookie dough around the Rolos, and anything that makes cookie baking easier is a total win!

Rolo cookies are always a favorite when it comes to holiday cookie platters and cookie exchanges, so bake up a batch of these chocolate chip Rolo cookies! Or maybe double it so you can have an entire batch to yourself!

Chocolate Chip Rolo Cookies

Chocolate Chip Rolo Cookies

Chocolate Chip Rolo Cookies

3 dozen
Prep Time:
10 minutes
Cook Time:
10 minutes
Total Time:
20 minutes



  • 2 ¼ cups flour
  • 1 tsp baking soda
  • 1 cup salted butter, softened
  • ¾ cup packed light brown sugar
  • ¼ cup granulated sugar
  • 1 (3.4-oz) package vanilla pudding mix
  • 2 eggs
  • 1 tsp vanilla extract
  • 2 cups semisweet chocolate chips
  • 36 Rolos


  1. Preheat oven to 350 degrees. Line a baking sheet with parchment paper or silicone baking mat.
  2. Combine flour and baking soda in a medium bowl; set aside.
  3. Cream together butter and sugars in a large bowl. Beat in instant pudding mix until blended. Add vanilla and eggs and mix well.
  4. Add flour mixture and mix until thoroughly combined. Fold in chocolate chips.
  5. Unwrap Rolos. Using a medium cookie dough scoop, shape a rounded heaping tablespoon of dough around each Rolo. Make sure candy is completely covered with dough. (I roll them in my hands to form a ball.)
  6. Place cookie dough on prepared baking sheet, about 2 inches apart. Bake 10 to 12 minutes. Remove from oven and let sit on baking sheet for 2 minutes. Transfer to cooling rack and cool completely.


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Nutrition Information:

Yield: 36

Serving Size: 1 cookie

Amount Per Serving:

Calories: 107Total Fat: 6gSaturated Fat: 3gTrans Fat: 0gUnsaturated Fat: 1gCholesterol: 24mgSodium: 113mgCarbohydrates: 12gFiber: 0gSugar: 8gProtein: 1g

© Emily Hill




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