Rolo Cookies

Chocolate Rolo Cookies

Here’s what I don’t understand. On Friday, I left work without a coat. It was in the lows 60s. Positively balmy. Warm enough that in the evening, we didn’t need coats on our walk with the dogs. And on Sunday, it snowed. And sleeted and hailed, then rained and hailed again.

Don’t get me wrong. I’m an advocate for snow. I love it, I always want it, I still think we didn’t get enough. But what is with it being hot then cold then hot again?  I can’t stand it! Luckily, it looks like the warm weather is on its way out for good this season and I can settle in for a nice, cold and snowy winter. Truly. The forecast for the next ten days has at least three snow showers. I’ll take it.


When there are snow showers, it’s time to do comforting things. Make soup. Drink hot chocolate on the couch while watching the Santa Claus. Bake. Always bake. Then bake some more. And since it is absolutely the Christmas season, baking is pretty much expected. These cookies are probably my new favorite. The cookie itself is somewhat like my favorite brownie. A bit chewy, a bit chocolately, not overly sweet. And then inside, the big surprise. The twist. The piece de resistance. A Rolo. The Rolo stays gooey, caramel and melty inside the cookie. It’s a flavor surprise of the best kind.

If you make giant cookie platters for work, family gatherings or parties, consider adding these to your list.

Chocolate Rolo Cookies
Recipe type: cookie
Prep time: 
Cook time: 
Total time: 


  • 2½ cups flour
  • ¾ cup unsweetened cocoa
  • 1 tsp. baking soda
  • 1 cup sugar
  • 1 cup brown sugar
  • 1 cup butter, softened
  • 1 tsp. vanilla
  • 2 eggs
  • 48 Rolos

  1. Preheat the oven to 375 degrees. Line two baking sheets with parchment paper.
  2. In a bowl, mix together flour, cocoa and baking soda. In the bowl of a stand mixer, combine sugar, brown sugar and butter until light and fluffy.
  3. Add vanilla and mix well. Add in eggs, one at a time, and mix until combined. Add in flour mixture and mix until combined.
  4. Take 1 tablespoon of dough and lay it in your hand. Take a caramel candy and put it in the center, then top with another tablespoon of dough to completely cover.
  5. Place on the baking sheet about 2 inches apart. bake for 12 to 15 minutes until the cookies set and begin to slightly crack. Transfer to a wire rack to cool.


9 thoughts on “Rolo Cookies

  1. Tell me about it – it was almost too warm here on Friday and then was absolutely freezing this weekend. I don’t like the flip flop weather – just pick cold already! And these cookies sound awesome – I haven’t had a rolo in years!

  2. Oh, yes! Rolos are one of my favorite candies that I don’t eat nearly enough as I should. I wouldn’t mind a little snow! It has been in the 80’s and the air conditioner is running again. Usually I don’t mind the warmer weather but in December around the holidays I expect a little chill.

    • Oh my, I can’t imagine running the AC this time of year. but I have to say, I’m definitely jealous. I’d love to have some warmer weather. :)

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