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a stack of rolo cookies on parchment paper.

Rolo Cookies with Gooey Caramel Centers

4.75 from 4 votes
These soft and chewy Rolo cookies are the ultimate chocolate-caramel treat. Each one hides a melty caramel center thanks to a Rolo candy tucked inside rich chocolate dough. They’re simple to make, totally irresistible, and perfect for holiday cookie trays, Valentine’s Day treats, or a cozy baking night at home.
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Prep Time20 minutes
Cook Time10 minutes
Chill Time2 hours
Total Time2 hours 30 minutes
Servings: 18 cookies

INGREDIENTS

  • 1/2 cup unsalted butter room temperature
  • 1/2 cup granulated sugar
  • 1/2 cup light brown sugar packed
  • 1 large egg room temperature
  • 1 teaspoon vanilla extract
  • 1 cup all-purpose flour gluten-free if needed
  • 2/3 cup natural cocoa powder
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 18-20 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).
  • Add the butter, granulated sugar and brown sugar to a large bowl using a hand-held or stand mixer fitted with a paddle attachment. Beat on medium-high speed for 3 minutes, until it's light and fluffy in color. With the mixer still on, beat in the egg and vanilla extract, scraping down the sides of the bowl as needed.
    1/2 cup unsalted butter, 1/2 cup granulated sugar, 1/2 cup light brown sugar, 1 large egg, 1 teaspoon vanilla extract
  • In a separate bowl, whisk the flour, cocoa powder, baking soda, and salt together until combined.
    1 cup all-purpose flour, 2/3 cup natural cocoa powder, 1 teaspoon baking soda, 1/2 teaspoon salt
  • Turn the mixer down to low and slowly add the dry ingredients to the wet ingredients and beat until combined.
  • Cover the dough with plastic wrap and chill in the refrigerator for at least 2 hours or up to 3 days.
  • Preheat the oven to 350°F and line two large baking sheets with parchment paper. If the dough was chilling for longer than 24 hours, allow it to soften at room temperature for 30 minutes.
  • Use a large cookie scoop, or 1/4 cup measuring cup, to scoop out the dough. Break each cookie dough ball in half and press a Rolo in the center. Place the other half on top then pinch and roll the seems so the Rolo is in the center.
    18-20 Rolos
  • Place the cookies 2-3 inches apart on the cookie sheet. Bake them in the preheated oven for 10-12 minutes, until the edges and tops are just set. Cool on the cookie sheet for 5 minutes then transfer them to a cooling rack to cool completely.

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 Rolos and frozen 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 at room temperature while the oven preheats then bake from frozen. Add 1-2 minutes to the bake them, if needed.
  • Chill the Dough: Chilling is essential for thick, chewy cookies and prevents spreading. If the dough chills longer than 24 hours, let it rest at room temperature for about 30 minutes before baking.
  • Use Room-Temperature Ingredients: This helps everything blend smoothly for a uniform dough and consistent baking.
  • Try Different Shapes: For extra-thick cookies, shape the dough into taller mounds (like a cone) before baking.
  • Make a Double Batch. You’ll understand when you take a bite.

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
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