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Caramel-Filled Chocolate Cookies

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By Pillsbury Kitchens
Updated Aug 2, 2022
Bake-Off® Contest 34, 1990
Jean Olson
Wallingford, Iowa
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Delicate pastry wraps chewy caramel and chocolate in this winning cookie.

More About This Recipe

  • Don’t be intimidated by these from-scratch stuffed Rolo™ cookies. They are much easier to make than they seem, and there are a few key tips that will make the process a breeze. First, don’t skip chilling the dough. Chilling cookie dough, even if for just 30 minutes, will make it much easier to handle. This makes it a crucial step for when you’re stuffing cookies with candy, like this recipe, or when you’re making sugar cookie cut-outs for Christmas like in this recipe. Working with the chilled dough on a floured surface with some flour on your hands will also make the dough easier to handle. Want more expert tips like these to make sure your cookies turn out perfect every time? From what kind of cookie sheet to use to how to ice cookies like pro, find out everything you need to know about baking cookies in our How to Make Cookies article. Then, keep the cookie party going by baking some more treats! Browse our giant cookie collection to find chocolate cookies, thumbprint cookies, Russian tea cakes and more.

Caramel-Filled Chocolate Cookies

  • Prep Time 1 hr 15 min
  • Total 1 hr 15 min
  • Ingredients 12
  • Servings 48
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Ingredients

  • 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
  • 48 Rolo® Chewy Caramels in Milk Chocolate, unwrapped (from 13-oz. pkg.)
  • 1 tablespoon sugar
  • 4 oz. vanilla-flavored candy coating, if desired

Instructions

  • Step 
    1
    In medium bowl, combine flour, cocoa and baking soda; mix well.
  • Step 
    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 of the pecans. If necessary, cover with plastic wrap; refrigerate 30 minutes for easier handling.
  • Step 
    3
    Heat oven to 375°F. For each cookie, with floured hands, shape about 1 tablespoon dough around 1 caramel candy, covering completely.
  • Step 
    4
    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.
  • Step 
    5
    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.
  • Step 
    6
    Melt candy coating in small saucepan over low heat, stirring constantly until smooth. Drizzle over cookies.

Nutrition

160 Calories
8g Total Fat
2g Protein
20g Total Carbohydrate
14g Sugars

Nutrition Facts

Serving Size: 1 Cookie
Calories
160
Calories from Fat
70
Total Fat
8g
12%
Saturated Fat
2g
10%
Cholesterol
10mg
3%
Sodium
85mg
4%
Total Carbohydrate
20g
7%
Dietary Fiber
1g
4%
Sugars
14g
Protein
2g
% Daily Value*:
Vitamin A
4%
4%
Vitamin C
0%
0%
Calcium
2%
2%
Iron
4%
4%
Exchanges:
1 1/2 Starch; 1 Fruit; 2 Fat;
*Percent Daily Values are based on a 2,000 calorie diet.
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