In the bowl of your stand mixer with the paddle attachment cream, the butter and sugars together for about 1-2 minutes.
Add in the eggs, egg yolks, and vanilla extract mixing until combined. Scrape down the sides before adding the dry ingredients. Mix until just incorporated
Add icing sugar, cinnamon, milk, and vanilla extract to a bowl. Whisk until all of the sugar is incorporated. Add additional milk as needed to thin but the glaze should be on the thicker side. Spoon glaze over cookies. Allow the glaze to dry before enjoying.