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    Home » Recipes » Dessert » Cookies

    Chocolate Caramel Rolo Cookies

    Published by Melissa on April 18, 2016 | Updated June 10, 2022 | 49 Comments

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    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.

    Featured Image for post Chocolate Caramel Rolo Cookies

    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.

    Chocolate caramel Role cookies on a brown plate

    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
    Print Recipe Pin Recipe Rate this Recipe
    4.40 from 33 votes

    Chocolate Caramel Rolo Cookies

    Prep Time40 mins
    Cook Time10 mins
    Total Time50 mins
    Course: Cookies
    Keyword: cookie, Dessert, food, recipe
    Servings: 2 ½ dozen
    Author: Barbara Schieving
    Prevent your screen from going to sleep

    Ingredients

    • 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

    Instructions

    • 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.

    Notes

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

    As of June 2022 Melissa Griffiths now is the one adding recipes. So think of it as Barbara Bakes, and Melissa too! Melissa and Barbara have been blogging friends for over 10 years and when Barbara was ready to retire and spend more time with her family, Melissa took over the site. Read more...

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      Recipe Rating




    1. Patrice Virata

      December 13, 2022 at 1:14 pm

      5 stars
      This was really good! Thank you for making the recipe so easy to understand and make! I added almonds as a topping and it makes a big difference in texture and taste. It was definitely a must to put on!

      Reply
    2. Rani

      June 27, 2021 at 12:55 am

      What would be the substitute for egg here? Would like to make it Eggless.

      Reply
      • Barbara Schieving

        June 27, 2021 at 3:46 pm

        Hi Rani – I’m sorry I don’t have much experience making eggless cookies.

        Reply
    3. Linda Wasko

      June 15, 2021 at 7:24 pm

      Barbara, help… I’ve been making these for years, but they always spread flat. They don’t look nice and round like yours. Am I baking too long maybe?

      Reply
      • Barbara Schieving

        June 16, 2021 at 3:25 pm

        Hi Linda – usually flat cookies need a little bit more flour. Just a couple of tablespoons can make a big difference. Are you cooking at altitude perhaps?

        Reply
    4. Cathrine

      December 04, 2020 at 3:43 pm

      My family absolutely loves this recipe!

      Reply
      • Barbara Schieving

        December 04, 2020 at 7:26 pm

        Thanks Cathrine – it’s a favorite at my house too.

        Reply
    5. Phyllis Richter

      November 17, 2020 at 9:40 am

      Our family doesn’t like nuts,so they omitt,but when the cookies are cooled you drizzle melted white chocolate over the top.Melt and put in zip bag and just zip over the top of cookies on waxed paper.yum!!!

      Reply
      • Barbara Schieving

        November 17, 2020 at 10:41 am

        That’s an awesome idea – thanks for sharing Phyllis!

        Reply
    6. Maryann

      November 13, 2020 at 3:12 pm

      Can I cut the Rolo in half so it doesn’t come out. 

      Reply
      • Barbara Schieving

        November 13, 2020 at 3:24 pm

        Hi Maryann – yes, you can cut them in half, just be sure to put the Rolo near the top of the cookie and cover it completely with cookie dough.

        Reply
    7. Diana

      October 16, 2020 at 6:27 pm

      The cookies were super yummy but baked up weird. Not sure what happened. The tops were nice and rounded out but didn’t quite hold up on bottom. I was afraid of overbaking and slid them off the baking rack 2 minutes after removing them from oven. The top was a shell and the caramel oozed out. No real bottom. Any tips for a solid cookie? Maybe I rolled cookie balls wrong? 

      Reply
      • Barbara Schieving

        October 17, 2020 at 6:10 am

        Thanks Diana – glad you enjoyed the cookies. I updated the post with additional information about shaping the cookies.

        Reply
    8. Michelle Kelley

      April 03, 2020 at 4:05 pm

      I adore these. One thing we’ve added is dipping them in pecans and a little sea salt. Then they get the salted caramel flavor. It’s amazing!

      Reply
      • Barbara Schieving

        April 03, 2020 at 4:07 pm

        It sounds like a delicious way to change them up – thanks for sharing Michelle!

        Reply
    9. Samantha Rizor

      November 05, 2019 at 5:24 am

      How many does this recipe make

      Reply
      • Barbara Schieving

        November 05, 2019 at 9:21 am

        Hi Samantha – about 2 1/2 dozen. Enjoy!

        Reply
    10. Andrew Parment

      September 14, 2018 at 7:41 am

      My grandmother has been making these cookies for as long as I can remember. Then my mother picked it up and modified. And then I found your recipe a few years ago they are easily the best I’ve had. I’ve even went ahead and used candy bars instead of rolos the possibilities are endless. Thank you so much for sharing this amazing recipe.

      Reply
      • Barbara Schieving

        September 14, 2018 at 8:09 am

        That’s great – thanks for sharing Andrew!

        Reply
    11. Shoba

      December 16, 2017 at 1:09 am

      What can I substitute eggs with?

      Reply
      • Barbara Schieving

        December 16, 2017 at 6:23 am

        Hi Shoba – I’m sorry I don’t have any experience using egg substitutes.

        Reply
    12. Shilpi

      December 15, 2017 at 2:37 am

      What is the substitute for rolo candy.. As m not going to get these in my city

      Reply
      • Barbara Schieving

        December 15, 2017 at 8:33 am

        You could substitute a piece of caramel like in these cookies https://www.barbarabakes.com/chewy-caramel-stuffed-sugar-cookies/

        Reply
    13. Jane

      December 19, 2016 at 5:37 pm

      These look wonderful, but I’m a little confused. The ingredients call for 1 c of nuts, and the recipe instructions only tell you what to do with 1/2 c of nuts. OK, Barbara…. fess up. Did you eat the other 1/2 c of nuts?? 🙂

      Reply
      • Barbara Schieving

        December 19, 2016 at 5:50 pm

        Hi Jane – thanks for the heads up. lol I’m not a huge nut lover, so maybe I subconsciously omitted adding the nuts in the dough. 🙂 I’d updated the recipe.

        Reply
    14. Lorraine @ Not Quite Nigella

      April 19, 2016 at 5:15 pm

      Ooh loving the sound of these mum! I’ve make a stuffed cookie and it was really good. But that was stuffed with a cookie. This is stuffed with chocolate and that is even more amazing! 😀 xxxx

      Reply
      • Shay

        December 24, 2019 at 12:02 pm

        I had my grandmother’s version of this recipe and over the years i misplaced it. I believe this recipe might be it or at the very least close to it. Everyone loved them! Thank you so much!

        Reply
        • Barbara Schieving

          December 24, 2019 at 1:49 pm

          That’s great – thanks Shay!

          Reply
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