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.
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.
Making Chocolate Caramel Rolo Cookies
When making these cookies, it’s important to place the Rolo near the top of the cookie dough. I like to use a #40 scoop and make a round ball. Then set the Rolo on top of the dough and push the dough up around the Rolo to cover it.
You want a nice thick base of cookie dough underneath the Rolo. The Rolo will melt while baking, and the more dough underneath the Rolo, the less likely it will be to leak out of the bottom.
It’s also important to use parchment paper or a Silpat when baking these cookies so they don’t stick to your baking sheet.
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.
Chocolate Caramel Rolo Cookies
- 2 ½ cups flour Pillsbury BEST® All Purpose or Unbleached Flour
- ¾ 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
- In a medium bowl, combine flour, cocoa, and baking soda; mix well.
- In a 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 ½ cup pecans if using.
- Cover the bowl with plastic wrap and refrigerate the dough for 30 minutes for easier handling.
- Preheat oven to 375°F. Line baking sheets with parchment paper or a Silpat.
- For each cookie, with floured hands, shape about 1 tablespoon dough around 1 Rolo candy, covering completely. **
- In a small bowl, combine the remaining ½ 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.
- 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.
**When making these cookies, it’s important to place the Rolo near the top of the cookie dough. I like to use a #40 scoop and make a round ball. Then set the Rolo on top of the dough and push the dough up around the Rolo to cover it.