Chipotle chile powder, made purely from ground chipotle peppers, gives a smokey heat to these crinkle cookies. Don't confuse it with regular "chili" powder, which includes additional spices like garlic and cumin.
Add the chocolate chips and butter to a small saucepan set over low heat. Cook, stirring frequently, until melted and smooth. Stir in the vanilla and set aside.
Beat the sugar and eggs until thick and smooth. Add the melted chocolate; mix to combine.
Sift in the flour, cocoa powder, cinnamon, chipotle powder, baking powder, and salt. Mix until combined. Cover with plastic and refrigerate until firm – about 1 hour.
Heat oven to 350ºF. Line your cookie sheets with parchment or a silicon mat. Pour the powdered sugar into a shallow dish.
Roll the dough into 1-inch balls, then roll the balls in the powdered sugar, coating them completely. Arrange the balls on the prepared cookie sheets. Bake 8-10 minutes, or until just set.