Add the butter and both types of sugar to the bowl of a stand mixer and cream together. (You can also use a hand mixer.)
Once combined add the eggs one at time and mix to until incorporated.
Mix in vanilla extract and the peppermint extract, if using.
Add the salt and baking soda to the flour and slowly add the flour to the butter mixture.
Add espresso powder, if using to the cocoa powder and add in small increments to the mixture. Beat on low speed until just combined being careful to not over mix the cookie dough.
Chill for 1 hour or up to 24 hours before baking cookies.
Once the dough has chilled preheat oven to 350° F and line a cookie sheet with parchment paper.
Using a #60 cookie scoop or tablespoon, portion the cookie dough and roll into a ball. Next, roll the dough ball in the sugar and place on the cookie sheet 2 inches apart.
Repeat with remaining dough and bake cookies in batches. Make sure to use a cool cookie sheet so the cookies do not spread.
Bake the cookies for 7-8 minutes. Have your Hershey candies ready to place on top of the cookies.
Place the unwrapped candies gently on top of the cookies, pressing down gently. Let the cookies cool on the cookie sheet so the Hershey Kiss keeps its shape.