Caramel-Filled Chocolate Cookies

Chelsea, Chelsea’s Messy Apron

These soft, bakery-style, double chocolate cookies have a surprise caramel center. These Caramel-Filled Chocolate Cookies will be a hit at any bake sale!
15 min Prep Time
12 min Cook Time
  • Prep Time: 15 min
  • Cook Time: 12 min
  • Servings: 3 dozen cookies

Servings: 3 dozen cookies


  • 1/2 cup (1 stick) unsalted butter, softened
  • 3/4 cup granulated sugar
  • 1/2 cup packed brown sugar
  • 1 large egg, at room temperature
  • 1/2 cup full fat sour cream, at room temperature
  • 1/2 teaspoon almond extract
  • 1 teaspoon vanilla extract
  • 1 3/4 cups all-purpose flour
  • 1/4 cup unsweetened cocoa powder
  • 1/4 cup special dark cocoa powder
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/4 cup miniature chocolate chips
  • 3/4 cup milk chocolate chips
  • 36 Rolo candies, unwrapped
  • Optional: sea salt


Step 1

In a large bowl, cream butter, sugar and brown sugar until light and fluffy (the mixture should resemble peanut butter). Add egg, sour cream, almond extract, and vanilla extract; beat to combine.

Step 2

In separate bowl combine flour, unsweetened cocoa powder, special dark cocoa powder, baking powder, baking soda, and salt. Stir to combine. Add chocolate chips and stir once more.

Step 3

Pour butter and sour cream mixture over dry ingredients and mix just until combined, being careful not to overmix. Cover dough and chill 1 hour.

Step 4

Preheat oven to 350?F. Line a baking sheet with parchment paper.

Step 5

For each cookie, take a heaping tablespoon of dough and shape it around an unwrapped Rolo, making sure the candy is completely encapsulated by dough. Place cookies on baking sheet 2 inches apart.

Step 6

Bake 10-15 minutes or until set (just until the top is no longer "glossy"). Be careful not to overbake. A soft, very slightly underbaked cookie is best for a delicious fudgy texture! If desired, add a sprinkle of salt to the tops of cookies. Cool 15-20 minutes before enjoying.