Preheat the oven to 350°F. Line a baking sheet with parchment paper.
In a large mixing bowl or the bowl of a stand mixer, beat the softened butter, powdered sugar, and vanilla extract on medium speed until light and smooth, about 3-5 minutes.
In another bowl, whisk together the flour, cinnamon, and salt.
With the mixer running on low, gradually add the flour mixture to the butter mixture. Mix just until a soft dough forms and no dry streaks remain. If the dough feels very sticky and does not hold its shape, sprinkle in 1 to 2 additional tablespoons of flour and mix briefly to combine.
In a shallow bowl or rimmed plate, stir together the powdered sugar and cinnamon for rolling.
Using a small cookie scoop (about 1 tablespoon) or a measuring spoon, portion the dough into 24 equal pieces. Roll each portion between your palms into a smooth ball, about 1 to 1 1/2 inches in diameter. Roll each ball in the cinnamon-sugar mixture to coat, then arrange on the prepared baking sheet, spacing them about 2 inches apart.
Bake for 15-18 minutes, until the cookies are set, the bottoms are lightly golden, and the tops look dry and slightly cracked.
Let the cookies cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely, about 30-45 minutes.
Serve right away or store in an airtight container.