Rolo Stuffed Cookies

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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.

For more of my favorite thick and chewy cookie recipes give my kitchen sink cookies or cookie monster cookies a try.

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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15 Comments

  1. Oh my. These sound so good. I love Rolo’s but I haven’t had them in a while. I can’t wait to make these. Thank you for sharing

  2. Wow, this looks scrumptious. Im excited about trying it out this weekend. My family has been asking for something new. Thank you for sharing it.

  3. 5 stars
    Wow, that looks like a skillet cookie cake — perfect to celebrate any party with 🙂 🙂 My kids will LOVE this. Thanks for sharing this yummy recipe.

  4. 5 stars
    This looks so delicious and so fun. It’s a perfect weekend family dessert. Cast iron skillet desserts are super easy to make. I can’t wait to try your recipe and serve it to my family.

  5. 5 stars
    I have been looking for a great skillet cookie recipe for a long time now thats not chocolate. I finally found one that I cant wait to try here and its so pretty thanks for sharing!

  6. 5 stars
    Aww, a frosted cookie!! So cute. Love the pretty pink. I would so be able to have the whole skillet all by myself. I am a huge cookie monster. Saving this for later.

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