Preheat your oven to 350°F (175°C). Gather all your ingredients and ensure your butter is at the right temperature—some cold and some softened.
In a small bowl, whisk together 6 tablespoons of all-purpose flour, 2 tablespoons of granulated sugar, 2 tablespoons of packed brown sugar, 1 teaspoon of ground cinnamon, and 1/2 teaspoon of salt. Cut in 3 tablespoons of cold unsalted butter until the mixture resembles coarse crumbs. Set aside.
In a large mixing bowl, combine 1/2 cup of room temperature unsalted butter, 1/2 cup of packed brown sugar, and 1/2 cup of granulated sugar. Using an electric mixer, cream them together until the mixture is light and fluffy.
Beat in 1 large egg and 1 teaspoon of vanilla extract until fully incorporated.
In another bowl, whisk together 2 cups of all-purpose flour, 2 tablespoons of cornstarch, 1 teaspoon of baking powder, 1/2 teaspoon of baking soda, 1/2 teaspoon of ground cinnamon, and 1/2 teaspoon of salt.
Gradually add the dry mixture to the wet mixture, mixing until just combined. Be careful not to overmix.
Scoop tablespoon-sized portions of the dough onto a baking sheet lined with parchment paper. Use a spoon to create a small well in the center of each cookie. Spoon a small amount of the cinnamon sugar mixture into the well.
Bake in the preheated oven for about 10-12 minutes, or until the edges are lightly golden. Remove from the oven and let cool on the baking sheet for a few minutes before transferring them to a wire rack.
In a small bowl, whisk together 1 cup of powdered sugar, 2 tablespoons of milk, and 1/2 teaspoon of vanilla extract (if using) until smooth. Drizzle over the cooled cookies.