Whip together softened butter and ½ cup powdered sugar. Add vanilla extract and pecans.
Add in flour ½ cup at a time to help incorporate all the ingredients together.
Using your hands finish combining and smashing the cookie dough together. Place in bowl and put into refrigerator.
Meanwhile preheat oven to 350 °F. Prep baking sheets with parchment paper. Set up wire rack and bowl of powdered sugar for rolling cookies in later.
Take dough out of fridge and roll 1 tbsp. in a ball to make cookies.
Optional: flatten cookie out in hand and place one cherry in the center. Roll dough around cherry.
Place all cookies 1 inch apart on baking sheet and bake for 12 minutes. Remove promptly from oven and transfer to wire rack to cool.
Cool for 5-10 minutes and then roll cookies in bowl of powdered sugar. Place in refrigerator to finish cooling.