Rolo Stuffed Cookies

5 from 15 votes
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These Rolo stuffed chocolate cookies are going to be a new family favorite. Delicious, soft, and chewy chocolate cookies with an ooey gooey caramel center.

Rolo stuffed chocolate cookies piled on wooded cutting board with one cookie sliced in half to show rolo inside.

What’s not to love about Rolo candies? You get the delicious chocolaty coating and then the rich, creamy, chewy caramel center.

But what if you surrounded that delicious candy in a chocolate cookie? It’s a cookie that everyone who loves chocolate and caramel are going to go fall in love with.

The Rolo flattens and melts a bit during baking, leaving the center of the cookie filled with the Rolo’s delicious, gooey caramel. Mmmmm so good! Especially when served warm, fresh from the oven with the center still gooey.

Chocolate cookie sliced in half to show caramel candy center.

Your family is going to go crazy for these homemade Rolo stuffed cookies. Enjoy them with milk, hot chocolate, or a nice cup of coffee. However you serve them, they are sure to be a big hit.

Looking for a cookie recipe for your annual Christmas cookie swap? These bad boys are perfect! If you want, you can make them a little bit more Christmasy by adding some green and red sprinkles on top.

These chocolate Rolo cookies would also make an amazing item for a bake sale because who can pass up caramel goodness?! No one. That’s right!

Looking for more stuffed cookie recipes? Try these homemade oatmeal cream pies, soft and chewy snickerdoodles or easy peppermint patty stuffed cookies. Both are incredible!

Recipe
Rolo stuffed chocolate cookies piled on wooded cutting board with one cookie sliced in half to show rolo inside.
Recipe
5 from 15 votes

Rolo Stuffed Chocolate Cookies

Author: Jaclyn
Prep: 20 minutes
Cook: 10 minutes
Total: 30 minutes
These Rolo stuffed chocolate cookies are going to be a new family favorite. Delicious, soft, and chewy chocolate cookies with an ooey gooey Rolo center. 

Ingredients
 

  • 2 ½ cups all-purpose flour
  • ¾ cup unsweetened cocoa powder
  • 1 teaspoon baking soda
  • 1 cup granulated sugar
  • 1 cup light brown sugar packed
  • 1 cup unsalted butter room temperature
  • 2 teaspoons vanilla extract
  • 2 large large eggs room temperature
  • 48 Rolo candies unwrapped

Instructions

  • Preheat oven to 375℉ degrees. Line 2 cookie sheets with parchment paper.
  • In a small bowl, whisk to combine flour, cocoa powder, and baking soda. Set aside.
  • Using an electric mixer, beat brown sugar, white sugar, and butter in a large bowl until smooth and creamy. Mix in vanilla and eggs. With the mixer on low slowly add flour mixture one Tablespoon at a time, mixing until just combined.
  • Chill cookie dough in the refrigerator for 15 minutes.
  • Scoop 1 Tablespoon of dough at a time and wrap it around a Rolo candy to form a ball. Place dough balls on the lined cookie sheet about 2 inches apart.
  • Bake at 375℉ for 7-10 minutes or until the cookies are set and just start to crack. Allow the cookies to cool on the cookie sheet for 4-5 minutes, then move to a wire rack.

Notes

Although best served warm, these cookies can be stored in an airtight container at room temperature for up to 4 days.

Nutrition

Calories: 126kcal | Carbohydrates: 18g | Protein: 1g | Fat: 6g | Saturated Fat: 4g | Polyunsaturated Fat: 0.2g | Monounsaturated Fat: 1g | Trans Fat: 0.2g | Cholesterol: 18mg | Sodium: 38mg | Potassium: 52mg | Fiber: 1g | Sugar: 12g | Vitamin A: 129IU | Calcium: 17mg | Iron: 1mg
Rolo stuffed chocolate cookies piled on wooded cutting board with one cookie sliced in half to show rolo inside.

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Ooey Gooey Rolo Stuffed Chocolate Cookies Pinterest image.

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Recipe Rating




15 Comments

  1. 5 stars
    Cookies are one of my very favorite treats! And if I can make it in one skillet instead of making perfect little rounds on a cookie sheet – well, that’s even better. I like the nice thick wedge — it looks so yummy. Great idea.

  2. 5 stars
    What a great way to celebrate with. Fun to make and fun to eat. The presentation is awesome….love my cast iron pans.

  3. 5 stars
    Perfect weekend bake to do with the kids.. so easy and it looks great. I have never made a skillet cookie.. where have i been!

  4. 5 stars
    What an awesome dessert idea! I love the idea of making a giant cookie in a skillet, it looks so amazing!

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