Chocolate Caramel Rolo Cookies

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Featured Image for post Chocolate Caramel Rolo Cookies

These prize-winning Chocolate Caramel Rolo Cookies are a family favorite. They’re an easy to make, rich, fudgy chocolate cookie stuffed with a Rolo candy.

My family is crazy about these cookies and we’ve been making for years. The cookie recipe was a $2,000 winner in the 1990 Pillsbury Bake-off. Stuffing a Rolo candy inside a chocolate cookie was a brilliant idea. How can you go wrong with the combination of chocolate and caramel. 

These prize-winning Chocolate Caramel Rolo Cookies are a family favorite. They\'re an easy to make, rich, fudgy chocolate cookie stuffed with a Rolo candy.

I originally posted these cookies in August 2008, the first year I started blogging. I’ve been trying to update my posts with better pictures, so when my husband made them again recently, I took some much better pictures.

These cookies are better if slightly underbaked. I’m not a nut lover, so when my husband made them this time, he omit nuts on half of them for me. He’s crazy about nuts and added pecans to his half. Either way, if you haven’t baked a Rolo cookie before, you need to get on that asap.

Featured Image for post Chocolate Caramel Rolo Cookies
Yield: 2 1/2 dozen

Chocolate Caramel Rolo Cookies

Prep Time 40 minutes
Cook Time 10 minutes
Total Time 50 minutes


  • 2 1/2 cups flour Pillsbury BEST® All Purpose or Unbleached Flour
  • 3/4 cup unsweetened cocoa
  • 1 teaspoon baking soda
  • 1 cup sugar
  • 1 cup firmly packed brown sugar
  • 1 cup margarine or butter, softened
  • 2 teaspoons vanilla
  • 2 eggs
  • 1 cup chopped pecans or walnuts
  • Rolo® Chewy Caramels in Milk Chocolate, unwrapped
  • 1 tablespoon sugar


  1. In medium bowl, combine flour, cocoa and baking soda; mix well.
  2. In large bowl, combine 1 cup sugar, brown sugar and margarine; beat until light and fluffy. Add vanilla and eggs; beat well. Add flour mixture; blend well. Stir in 1/2 cup pecans if using.
  3. If necessary, cover with plastic wrap; refrigerate 30 minutes for easier handling. Heat oven to 375°F.
  4. For each cookie, with floured hands, shape about 1 tablespoon dough around 1 Rolo candy, covering completely.
  5. In small bowl, combine remaining 1/2 cup pecans and 1 tablespoon sugar. Press one side of each ball into pecan mixture. Place, nut side up, 2 inches apart on ungreased cookie sheets.
  6. Bake at 375°F. for 7 to 10 minutes or until set and slightly cracked. Cool 2 minutes; remove from cookie sheets. Cool on wire rack for 15 minutes or until completely cooled.


*Omit nuts and 1 tablespoon sugar if you prefer. Slightly adapted from Pillsbury Bake Off recipe

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