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gooey caramel melting out of a rolo cookie
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5 from 3 votes

Rolo Cookies

These Rolo cookies are soft and chewy chocolate cookies with Rolo candies inside! The cookie dough is rich and chewy and the melted chocolate and caramel are a fun surprise inside. Top with sea salt and enjoy!
Prep Time20 minutes
Cook Time10 minutes
Chill Time2 hours
Total Time2 hours 30 minutes
Servings: 18 cookies

Ingredients

  • 1 1/2 cups all-purpose flour or 1:1 gluten free flour
  • 1 cup natural unsweetened cocoa powder
  • 3/4 teaspoon kosher salt
  • 1 1/2 teaspoons baking soda
  • 3/4 cup 1 1/2 sticks unsalted butter softened to room temperature
  • 1/3 cup granulated sugar
  • 1 1/3 cup light brown sugar packed
  • 2 large eggs room temperature
  • 1 teaspoon pure vanilla extract
  • Rolos unwrapped

Instructions

  • Note: This cookie dough requires at least 2 hours of chilling. The cookies will be thicker the longer they chill (up to 3 days).
  • Whisk the flour, cocoa powder, baking soda and salt together in a medium bowl.
  • In a large bowl using a hand mixer or stand mixer fitted with the paddle attachment, beat the butter, granulated sugar and brown sugar on high speed until smooth and creamy, 2-3 minutes. Do not skip this step.
  • Add the egg and vanilla. Beat on medium-high speed until combined, another 1-2 minutes. Scrape down the bottom and sides of the bowl with a rubber spatula as needed.
  • With the mixer running on low speed, slowly add the dry ingredients in 3 different parts, beating well after each addition.
  • Scoop the cookie dough into balls, about 1 Tablespoon each. Stuff them with Rolos by making an indent with your thumb in a dough ball and placing the Rolo inside. place another ball of dough on top and roll them together to create one larger dough ball. Place on the prepared baking sheet. Repeat with all of the dough. Place the baking sheet in the fridge for 1.5 - 2 hours to chill or in the freezer for 1 hour.
  • Preheat the oven to 350°F. Line another baking sheet with parchment paper.
  • Place the cookies 3 inches apart on the baking sheet. Bake in the preheated oven for 10-12 minutes, until just set on top.
  • Allow cookies to cool for 5 minutes on the baking sheet then transfer to a wire rack to cool completely
  • Cookies remain soft and fresh in an airtight container for 7 days at room temperature.

Notes

  • Make-ahead: make the dough up to 3 days in advance, cover and chill in the fridge until you're ready to bake. The longer you chill the dough, the better so this is a perfect make-ahead cookie.
  • To store: baked cookies with the Rolos will stay fresh at room temperature in an airtight container for up to 4 days or in the fridge for up to 1 week.
  • Freezer: baked cookies with the Rolos freeze well for up to 3 months. Thaw overnight in the fridge and enjoy. You can also freeze the cookie dough for up to 3 months. Stuff the cookie dough with the Rolos then place them on a baking sheet in the freezer for 30 minutes to flash freeze. Transfer them to a freezer bag and remove as much air as possible. Allow to sit a room temperature while the oven preheats then bake from frozen. Add 1-2 minutes to the bake them, if needed.

Nutrition

Serving: 1cookie | Calories: 224kcal | Carbohydrates: 33.1g | Protein: 3.1g | Fat: 10.2g | Cholesterol: 41.7mg | Sodium: 182.2mg | Fiber: 2.1g | Sugar: 22.1g | Vitamin A: 75.6IU | Vitamin C: 0.1mg