Line 2 large baking sheets with parchment paper. Set aside.
In a medium bowl, whisk the flour, unsweetened cocoa powder, cornstarch, and salt together. Set aside for now.
1¼ cups all-purpose flour, ⅓ cup unsweetened cocoa powder, 1 teaspoon cornstarch, ¼ teaspoon kosher salt
In a large bowl, using a hand mixer, beat the butter, brown sugar, and granulated sugar together on high until light and fluffy, about 2 minutes.
½ cup unsalted butter, ½ cup brown sugar, ¼ cup granulated sugar
Beat in the egg and vanilla extract until fully combined, about 30 seconds.
1 large egg, 2 teaspoons pure vanilla extract
Beat the dry ingredients into the wet ingredients on low just until combined. Do not overmix.
Fold in the mini chocolate chips with a rubber spatula – don’t use the electric mixer for this step. Over mixing the dough can lead to dry cookies.
½ cup mini semisweet chocolate chips
Cover the bowl with plastic wrap and place it in the refrigerator for 30 minutes to chill before rolling out.
When ready to roll out cookies, lightly dust a clean work surface with flour.
Place about ⅓ of the dough on the work surface and start to roll it out. Lightly dust the top of the dough with flour if the dough is sticking to the rolling pin. To keep these cookies thick and chewy, they should be rolled out to ⅜-inch thickness.
Using a crinkle cutter or sharp knife, cut the cookie fries about ½-¾ inch in width and between 4 and 5 inches long. You’ll want to vary the length a bit between 4 and 5 inches long so they aren’t all the exact same length – just like regular French fries.
Place the raw cookie dough fries about 1½ inches apart on the prepared baking sheets. The cookies shouldn’t spread much during baking but leave a little bit of space between fries for growth.
Place the cookie fries into the freezer to chill for 20 minutes.
While the cookies chill, preheat the oven to 350°F.
Place one tray of cookie fries into the oven on the center rack to bake for 12-13 minutes. The cookies will still look soft and slightly underbaked. This is good! This results in chewy – not crunchy – cookie fries. They’ll continue baking on the hot tray after they’ve been removed from the oven.
Bake the second sheet of cookie fries following the same steps above.
For the caramel dip, place the brown sugar, heavy cream, butter, and vanilla extract in a small saucepan. Bring to a boil over medium heat, stirring constantly. Reduce heat to low and simmer for 10 minutes, stirring often. Serve the cookies with the caramel sauce.
½ cup brown sugar, ¼ cup heavy cream, 2 tablespoons unsalted butter, 1 teaspoon pure vanilla extract