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Caramel Filled Chocolate Sugar Cookies stacked up.
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5 from 20 votes

Caramel filled chocolate sugar cookies

Ooey-gooey caramel-filled chocolate sugar cookies will knock your socks off! Crispy on the outside, gooey on the inside.
Prep Time10 mins
Cook Time8 mins
Total Time18 mins
Course: Dessert
Cuisine: American
Keyword: cookies
Servings: 24 cookies
Calories: 125kcal
Author: Anna


  • 1.25 cup all-purpose flour
  • 6 Tbsp unsweetened cocoa powder
  • 1/2 tsp baking soda
  • 1/2 cup granulated sugar
  • 1/2 cup packed light brown sugar
  • 1/2 cup unsalted butter room temperature
  • 1 tsp vanilla extract
  • 1 large egg
  • 15 to 18 Rolos candies unwrapped
  • 2 Tbsp granulated sugar for rolling


  • Place butter in large mixing bowl. Beat with an electric mixer for 20 seconds. Add both sugars, egg and vanilla and mix well until everything is blended well.
  • In another mixing bowl, sift together the dry ingredients (flour, cocoa and baking soda). Add to the wet ingredients in three additions. Mix until all of the dry ingredients are incorporated.
  • Cover the bowl and refrigerate the dough for 30 minutes.
  • Preheat the oven to 375 degrees F.
  • Line a cookie sheet with a parchment paper or s silicone baking mat. Set aside.
  • Place the 2 tablespoons of sugar in a small bowl.
  • Scoop the cookie dough with a standard size ice cream scoop, leveling on the side of the bowl.
  • Roll the dough in your hands into a ball. Place a Rolo candie top side down into the dough ball, push down and cover with the dough on the sides. Roll again in your hands to make a ball.
  • Roll in sugar, place on prepared baking sheet.
  • Repeat with the rest of the dough, placing 6 balls of dough on a sheet at a time.
  • Bake for 7 to 9 minutes (8 minutes was the magic time for me). Cool on the sheet for 2 minutes, gently transfer onto a cooling rack.


Calories: 125kcal | Carbohydrates: 20g | Protein: 1g | Fat: 4g | Saturated Fat: 2g | Cholesterol: 17mg | Sodium: 46mg | Potassium: 49mg | Sugar: 13g | Vitamin A: 130IU | Calcium: 17mg | Iron: 0.6mg