Gooey Caramel-Filled Chocolate Cookies

TGIF, friends! This has seriously felt like the longest week ever, probably because I’m so excited about the weekend. If you’re a longtime reader, you’ll know I’m kind of a sports fanatic, and this weekend is big. Tomorrow night is the first game of the season for the Bruins (and it should be a good one against the Rangers!), and then on Sunday, the Pats are playing in the AFC Championship. Keeping my fingers crossed for another trip to the Super Bowl! :)

I’ve been pinning “game day” recipes all week. Although we’re not hosting a get-together until the Super Bowl, I can’t help myself – I will definitely be putting together a few fun treats for just the two of us to munch on while watching the games this weekend. And rest assured that if any of the recipes are a hit, I’ll be sharing them with you soon!

Gooey Caramel-Filled Chocolate Cookies

I won’t lie, these cookies have been sitting in my archives waiting to be shared since early last fall. I made them for a football weekend way back in October, and then they got buried in my drafts folder. I’m not even sure how I let that happen but it’s time to remedy the situation.

These cookies utilize one of my favorite candies of all time – Rolos. Every time I’m in line at the grocery store and see them in the candy display I’m so, so tempted to throw a roll (or two or three) in my cart. Here the Rolos are stuffed inside a rich chocolatey dough and baked so you wind up with a soft, chewy cookie with a gooey caramel center. They’re easy to make (though unwrapping the Rolos is kind of tedious) and completely irresistible! As I often do, I microwaved the leftover cookies for a few seconds to recreate that warm from the oven texture. It was the perfect treat to satisfy a chocolate craving, and dare I say my love of the chocolate/caramel combo is right up there with chocolate/peanut butter these days?!

Gooey Caramel-Filled Chocolate Cookies

Gooey Caramel-Filled Chocolate Cookies
from Iowa Girl Eats

1 1/4 cups all-purpose flour
1/4 cup plus 2 tablespoons unsweetened cocoa powder
1/2 teaspoon baking soda
1/4 teaspoon salt
1/2 cup (1 stick) unsalted butter, at room temperature
3/4 cup granulated sugar, divided
1/2 cup packed light brown sugar
1 large egg
1 teaspoon vanilla extract
24 rolos

Preheat oven to 375 F. Line two baking sheets with parchment paper.

In a medium bowl, whisk together the flour, cocoa powder, baking soda, and salt. In the bowl of a stand mixer fitted with the paddle attachment, cream the butter, 1/2 cup of the granulated sugar, and the brown sugar together on medium speed until light and fluffy, about 3-4 minutes. Mix in the egg and vanilla extract. With the mixer on low, gradually add the dry ingredients, beating just until combined. Refrigerate the dough for 1 hour.

Place the remaining 1/4 cup granulated sugar in a wide shallow bowl. Portion the dough into about 1 tablespoon balls. Working with one ball of dough at a time, press one rolo into the center and then enclose the rolo completely with the dough. Reform the dough into a ball. Roll in the granulated sugar and transfer to the prepared baking sheet. Repeat with all the dough, spacing the cookies about 2 inches apart on the baking sheets.

Bake for 7-9 minutes, or until the edges are just barely set. Transfer the baking sheet to a wire rack and allow the cookies to cool for a few minutes then remove them to the racks. I liked these best slightly warm from the oven, so I popped leftovers into the microwave for a few seconds to recreate the same texture.

Makes about 2 dozen cookies