Combine flour, salt, and ½ cup powdered sugar (reserve the other half) into a large bowl and cut in butter. Add 1 tablespoon of cinnamon and vanilla extract. Use an electric mixer (dough hook attachment) to knead the dough until well combined. Mix in chocolate chips and dried cherries.
Use a tablespoon (or a retractable ice cream scoop) to measure 1-inch balls. Shape dough balls until smooth and place onto an ungreased baking sheet.
Bake for 7-8 minutes. Transfer cookies onto a wire cooling rack. Cool for 10 minutes.
Sift the remaining ½ cup of powdered sugar into a shallow bowl and combine with the remaining 1 tablespoon of cinnamon.
Roll lightly cooled cookie balls in the cinnamon sugar until well coated. Return to the wire rack and let cool completely.