Preheat oven to 350°F and line three baking sheets with parchment paper.
Cream butter and granulated sugar on medium speed with a mixer until combined and fluffy. Add vanilla and eggs; mix until just combined.
Whisk together flour, powdered sugar, baking powder, cinnamon, and salt. Add half of flour mixture to the butter mixture. Mix on low speed until just combined, and then medium speed until completely combined. Repeat with second half of flour mixture. The dough will be a little soft.
For the cinnamon-sugar coating, stir together sugar and cinnamon in a shallow bowl. Using a cookie scoop (I used a 1 1/2-inch scoop), place one scoopful of dough into the coating mixture. Use a spoon to coat cookie dough with cinnamon-sugar, turning the dough over to make sure it's evenly coated. Transfer to the prepared baking sheet, arranging 2-inches apart. (I got 8 cookies on two baking sheets and 6 on the third.)
Bake cookies for 6-8 minutes, or until crisp around the edges. Let cookies cool on pans for a few minutes before transferring to a cooling rack.