In a small bowl, combine the flour, brown sugar, cinnamon, and salt for the streusel.
Add melted butter and stir with a fork until coarse crumbs form. Set aside.
In a medium bowl, whisk together flour, baking soda, baking powder, salt, and cinnamon.
In a large bowl, beat softened butter, granulated sugar, and brown sugar for 2–3 minutes, until light and creamy.
Add the egg and vanilla extract and mix until combined.
Stir in the sour cream.
Gradually add the dry ingredients to the wet mixture.
Mix just until the flour disappears. Do not overmix.
Cover the dough and refrigerate for 30 minutes.
Preheat the oven to 350°F (175°C) and line two baking sheets with parchment paper.
Scoop approximately 1½ tablespoons of dough for each cookie and roll into balls.
Place the dough balls on the prepared baking sheets, leaving about 2 inches between each cookie.
Gently flatten each cookie and make a shallow indentation in the center.
Fill each indentation generously with the prepared cinnamon streusel.
Bake for 10–13 minutes, until the edges are lightly golden and the centers remain soft.
Cool the cookies on the baking sheet for 5 minutes, then transfer them to a wire rack.
Allow the cookies to cool completely.
To make the glaze, whisk powdered sugar, milk, and vanilla until smooth.
Drizzle the glaze over the cooled cookies.
Let the glaze set for several minutes before serving.