Preheat the oven to 350 degrees and line 2 baking sheets with parchment paper. Set aside.
Ensure your Hershey Kisses are unwrapped and placed in the freezer.
In a small to medium-sized bowl, combine the flour, cocoa powder, corn starch, cinnamon, baking powder, baking soda, and salt. Whisk with a fork. Set aside.
In the bowl of a stand mixer fitted with the paddle attachment, cream the butter and brown sugar on medium-high speed until light and fluffy, about 2-3 minutes.
Scrape down the sides and bottom of the bowl. Add the whole egg and egg yolk, mixing on medium speed for 30 seconds each.
On low speed, add the vanilla extract and mix just until combined.
Gradually add the mixed dry ingredients on low speed, mixing just until incorporated and no flour streaks remain.
Use a 1 or 2 tablespoon cookie scoop to form 12 dough balls per cookie sheet.
Roll each ball in granulated sugar until coated, then arrange on the baking sheets about 2-3 inches apart. You will use one pan twice.
Bake the cookies for 7-8 minutes, checking at the 7-minute mark as they bake quickly.
As soon as the cookies are done baking, press a frozen Candy Cane Kiss into the center of each cookie.
Let the cookies cool completely on the baking sheets until the Kiss is set, then transfer them to a cooling rack.