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Chocolate Crinkle Cookies with a Rolo Surprise

Make people “OOooo!” and “Mmmmm!” as they discover the treasure hiding inside these chocolatey cookies!
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Course: Dessert
Cuisine: American
Prep Time: 20 minutes
Cook Time: 10 minutes
Refrigerate: 2 hours
Servings: 24 cookies
Calories: 193kcal
Author: Megan Porta


  • 2 cups all-purpose flour
  • 3/4 cup unsweetened cocoa powder
  • 1/4 cup cocoa powder preferably use "black cocoa powder"
  • 2 tsp. baking powder
  • 1 tsp. salt
  • 10 tbsp. unsalted butter softened
  • 1 1/2 cups granulated sugar
  • 2 eggs
  • 2 tsp. vanilla extract
  • 1 cup powdered sugar
  • 24 chocolate-covered caramel candies (such as Rolos), unwrapped


  • In a medium bowl, combine the flour, cocoa powders, baking powder and salt. Set aside.
  • Using a hand-held mixer on medium speed, combine the butter, sugar, eggs and vanilla until smooth. Gradually add the flour mixture and mix until just combined. Pat the batter into a giant ball and wrap up in plastic wrap. Refrigerate for a minimum of 2 hours, or until completely chilled.
  • Preheat oven to 350 degrees F. Line two large baking sheets with parchment paper and set aside. Pour the confectioners’ sugar into a small bowl and set aside.
  • Remove the chilled dough from the refrigerator. Scoop out a large spoonful of dough and flatten it into a disc using your fingers. Place a chocolate-covered caramel into the center and wrap the dough around it, forming a ball. Smooth out the creases in the dough as much as possible. Roll the ball in the confectioners’ sugar twice, completely covering it both times, and set on the prepared baking sheets. Repeat this process with the remaining dough. Bake in the preheated oven for 10 minutes.


Calories: 193kcal | Carbohydrates: 32g | Protein: 3g | Fat: 7g | Saturated Fat: 4g | Cholesterol: 28mg | Sodium: 142mg | Potassium: 84mg | Fiber: 2g | Sugar: 21g | Vitamin A: 181IU | Vitamin C: 1mg | Calcium: 43mg | Iron: 1mg
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