In large bowl, mix together flour, powdered sugar, cinnamon and salt.
Cut in butter, using pastry blender or fork, until mixture looks like coarse crumbs.
Stir in chocolate chips and vanilla (mixture will be crumbly).
Using hands, shape dough into 1-inch balls. On ungreased cookie sheets, place balls 1 inch apart.
Bake 6 to 8 minutes or until set but not brown. Immediately remove from cookie sheets to cooling racks. Cool slightly, about 20 minutes.
In small bowl, stir together powdered sugar and 1 teaspoon cinnamon. Roll cookies in sugar mixture, shaking off excess back into bowl. Cool completely, about 30 minutes.
Notes
When the recipe says the dough will be crumbly, I'm not kidding. We found it better to work as a tag team—one person scooped the dough in the mini-scoop and the other person did the rolling of the dough balls. We had to kind of squeeze the dough to get it to combine enough to roll it. They balls did kind of flatten out during baking so don’t expect them to stay totally round. Still tasty though!