Caramel Stuffed Mexican Chocolate Cookies

A funny thing happens when I have conversations with other cooks and bakers (I will avoid the use of the word “foodie” even though I don’t really have much of a problem with it myself.)… No matter where the conversation starts (vacation plans, new jobs, etc.), we usually end up talking about food. More specifically, we often end up scheming a whole litany of ideas for new recipes.

This is typically the case every time I meet up with my good buddy Amber on Skype.  And for whatever reason, Amber and I rarely come up with healthy recipes when we put our minds together. Instead, we come up with evil ideas for food… You know, those horribly evil recipes that are no good for you but taste absolutely amazing? Yup, we’re’ pretty good at dreaming those up.

In a conversation a few weeks ago, we started out discussing perfectly innocent topics like our upcoming travel plans… But, the conversation quickly turned to junk food and cookies.  Unfortunately (or maybe fortunately?), pregnancy has kind of ruined my sweet tooth, and I haven’t been able to really eat any of the sweets that I’ve baked over the past 6 months. Of course, that doesn’t mean that I can’t dream them up and live vicariously through Amber, right?

Here’s the problem… A day or so after chatting with Amber, I still had cookies on the brain.  In fact, I had these particular Caramel Stuffed Sugar Cookies on the brain (since we had been discussing the intricacies of baking with Milk Duds).  Then it hit me… I had to make a new Mexican chocolate version of the cookies. So, I set out with my cinnamon and chipotle chili powder in hand and started mixing up some cookie dough.  I knew I wouldn’t be able to eat them, but there would be plenty of others who would enjoy sampling the cookies on my behalf.

In the end, they turned out better than I had expected.  My hubby instantly loved them, proclaiming that they were some of the best cookies I’ve ever made, and my parents also raved about them. I even tried one or two myself… And, I can attest to the fact that they are good. I think they are better than the sugar cookie version I made last year.

This recipe is definitely a keeper… The cookies are soft and chewy with a nice caramel layer tucked into the middle.  The chipotle adds just enough of a kick that you notice it, but doesn’t overpower the cookies with heat. Don’t believe me? Try them for yourself!

Caramel Stuffed Mexican Chocolate Cookies
Makes 3 1/2 dozen
(Adapted from my Caramel Stuffed Sugar Cookies)

• 1 cup (2 sticks) unsalted butter, at room temperature
• 3/4 cup granulated sugar
• 1/2 cup packed dark brown sugar
• 1/4 cup corn syrup
• 1 egg
• 1 teaspoon pure vanilla extract
• 2 1/2 cups all purpose flour
• 3/4 cup cocoa powder
• 1 1/2 teaspoons baking powder
• 1 teaspoon ground cinnamon
• 1/2 teaspoon baking soda
• 1/2 teaspoon salt
• 1/4 teaspoon chipotle chili powder
  (Use 1/2 teaspoon for a cookie with more of a kick!)
• 5 ounce box Milk Duds
• Additional granulated sugar (about 1/2 cup) for coating cookies

Preheat the oven to 375°F.  Line baking sheets with silicone mats or parchment paper and set aside.

In a large mixing bowl, combine the butter, granulated sugar, and dark brown sugar.  Beat well (with a hand mixer or a stand mixer) on medium-high speed for about 2-3 minutes, until the mixture is light and fluffy.  Add in the corn syrup, egg, and vanilla, and beat for an additional minute.

Meanwhile, whisk together the flour, cocoa powder, baking powder, cinnamon, baking soda, salt, and chipotle chili powder. Add the dry ingredients to the creamed mixture and mix on the lowest setting just until the dry ingredients are incorporated into the batter.

Scoop out rounded tablespoons (or use a medium cookie scoop) of dough.  Tuck one Milk Dud inside each ball of dough and roll the dough back into a ball to completely cover the candy.  Roll the cookie in the additional granulated sugar and place on the cookie sheet.

Bake the cookies for approximately 10 minutes, until they are just set and have a few cracks on the top.  Cool on the pan for 5 minutes before transferring to a wire rack to cool completely.