Chocolate Caramel-Filled Cookies. White Chocolate Drizzle Optional.

OH SNAP. It’s on. It’s Christmas season, we had a little CrossFit get together for the holidays and you bet your last protein shake that I was in charge of dessert. Faileo tiiiime. I consider these well worth it. These are the cookies that won the ESPN Travel cookie contest in 2007 and 2008. Even though it means nothing to any of you, to me it meant a free cooking class at Sur La Table and bragging rights for a year. My ego likes stuff like that.



Chocolate Caramel-Filled Cookies
(White Chocolate Drizzle Optional. I recommend it for aesthetics.)

Ingredients are as follows:

  • 1 bag Rolo Candies
  • 2 1/4 cups Flour
  • 3/4 cup Baking Cocoa
  • 1 tsp Baking Soda
  • 1 cup Sugar
  • 1 cup Brown Sugar
  • 1 cup (2 sticks) Butter, softened
  • 2 Eggs
  • 2 tsp Vanilla Extract

Step 1) The recipe I got from Mom says to grab a bowl that isn’t your mixer, combine the following ingredients: Flour, Cocoa, Baking Soda. I did not listen to this. I skipped to step 2 first, then doubled back and just tossed it all in. End result looks the same. So HAH.

Step 2) In your mixer (gahhh I love my Kitchen-Aid so much), beat both sugars and your butter until it’s a fluffy consistency. Then add in the eggs and vanilla. I was so excited I saved the dough from a broken egg yolk as I was separating the egg white into the mixer. I then realized I was unnecessarily separating the egg out of habit of making omelets all the flipping time. Broken yolk, you go into the cookies too.

Step 3) Now you’re supposed to add the Step 2 mixture to the Step 1 mixture. See… this was kind of a moot step for me. Moving on.

Cookie Collage 1

Step 4) Chill the dough for at least an hour. It will make it much easier to work with when it comes time for the magic caramel filling.

Step 5) While that’s in the fridge and you’re done having your 1990’s pop music dance party, unwrap the Rolo candies. Totally tedious, but a necessary evil. Watch some TV. Do the dishes. Do whatever it is that you people do to make the next hour or two pass by.

Step 6) Time to get ROLLIN’ ROLLIN’ ROLLIN’ – sorry, 2001 Fred Durst moment. This is a great time to get your kids or sucker of a significant other to get in the kitchen to help you out, especially if you’re into the whole assembly line idea. My Mom used to make me help her with these all the time. You’re going to have few things going on here:

  • Get your cookie sheets set up. This recipe is a fantastic opportunity for you to appreciate the virtues of parchment paper. If you want to proceed with an ungreased cookie sheet, go for it. Just don’t come complaining to me if there’s some caramel ooze that makes things all messy.
  • You’ll need a separate bowl/dish of white sugar to roll each cookie in. Make like Tonto and jump on that.
  • Hopefully you didn’t eat too many of those Rolo candies during the chill break. You’re going to need them all. I ate two. I ended up ONE short at the end of this batch. Bah humbug.

Take approximately a tablespoon of dough and a Rolo. Press it into the dough to get it going, and then use your hands to roll it into a ball until the Rolo has magically disappeared. From there, roll each ball around in the white sugar until it’s fully coated.

Camera Roll2

Park each ball on the cookie sheet, leaving at least 2in of space between each cookie. Bake at 375 degrees for 7-10 minutes. Reason the time range is so large, is because some people’s eyeballed tablespoons are a lot larger than others. You want the cookies to end up slightly cracked around the edges. Just like my sense of humor.

OPTIONAL: White Chocolate Drizzle. It’s so easy and makes these babies look that much cooler.

Get some white chocolate chips. Melt them. Microwave, double boiler, whatever tickles your fancy. Grab a fork, cover it in chocolate and kind of wave it back and forth over the cookies like you’re casting a magic spell on them. A magic spell of MMMTHESECOOKIESAREDELICIOUS! Shazam. This should go without saying, but I’ll say it to cover my butt anyway. Don’t be stupid and try to stack the cookies until the chocolate has hardened.

Then… be a doofus like me and instagram the you-know-what out of these. They were a labor of lurrrve.


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