In a large bowl, combine crushed cookies, pecans, 1 cup powdered sugar, and cinnamon until mixed.
Whisk together bourbon and maple syrup, then pour over dry ingredients. Mix well until evenly moistened. It should easily clump together but not be soggy. Add more powdered sugar or maple syrup as needed.
Pour the rest of the powdered sugar into a bowl. Shape the cookie mixture into 1-inch balls using your hands or a cookie scoop, then roll in powdered sugar to coat completely. Place on a tray and repeat until all is used.
Chill the bourbon balls for at least 30 minutes to set and bring out the bourbon flavor before enjoying.