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.
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!
What would be the substitute for egg here? Would like to make it Eggless.
Hi Rani – I’m sorry I don’t have much experience making eggless cookies.
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?
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?
My family absolutely loves this recipe!
Thanks Cathrine – it’s a favorite at my house too.
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!!!
That’s an awesome idea – thanks for sharing Phyllis!
Can I cut the Rolo in half so it doesn’t come out.
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.
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?
Thanks Diana – glad you enjoyed the cookies. I updated the post with additional information about shaping the cookies.
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!
It sounds like a delicious way to change them up – thanks for sharing Michelle!
How many does this recipe make
Hi Samantha – about 2 1/2 dozen. Enjoy!
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.
That’s great – thanks for sharing Andrew!
What can I substitute eggs with?
Hi Shoba – I’m sorry I don’t have any experience using egg substitutes.
What is the substitute for rolo candy.. As m not going to get these in my city
You could substitute a piece of caramel like in these cookies https://www.barbarabakes.com/chewy-caramel-stuffed-sugar-cookies/
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?? 🙂
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.
Lorraine @ Not Quite Nigella
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
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!
That’s great – thanks Shay!