Preheat the oven to 350°F.
Line two cookie sheets with parchment paper.
In a stand mixer add the butter, 1/2 cup powdered sugar, and vanilla. Mix on medium speed until light and fluffy.
Carefully add flour mixture, 1 cup at a time, to the butter mixture. Mix until the dough comes together.
Using a small ice cream scoop, scoop balls of dough. Take 1 dough ball at a time and flatten it out with your hand. Place a Hershey Kiss chocolate in the center. Roll the dough back into a ball.
Place the rolled Hershey Kiss cookies on the baking sheet, about 2 inches apart.
Bake cookies for 8-10 minutes until the bottoms start to become golden brown.
Remove from the oven and cool for just 5-10 minutes.
In a small bowl add your powdered sugar, then roll each cookie in the sugar until coated.