Brown Sugar Pop Tart Cookies

Cookies:

1 cup unsalted butter, room temperature

1/2 cup granulated sugar

1 cup light brown sugar, packed

2 eggs, room temperature

1 teaspoon vanilla extract

3 3/4 cups cake flour

2 tablespoons cornstarch

1 teaspoon baking soda

1 1/2 teaspoons baking powder

1 teaspoon kosher salt

Brown Sugar Filling:

5 tablespoons unsalted butter, softened

3/4 cup light brown sugar, packed

1 teaspoon cinnamon

2 tablespoons cake flour

Brown Sugar Glaze:

1 cup powdered sugar

1/2 teaspoon cinnamon

3 tablespoons unsalted butter, melted and cooled

2 1/2 tablespoons milk

Prepare the Filling: In a bowl, mix softened butter, brown sugar, cinnamon, and cake flour until well combined. Set aside.

Make the Cookies: Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.

In a large bowl, cream together butter, granulated sugar, and brown sugar until light and fluffy.

Add eggs one at a time, mixing well after each addition. Stir in vanilla extract.

In a separate bowl, whisk together cake flour, cornstarch, baking soda, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, stirring until just combined.

Scoop dough into balls, flatten slightly, and add a small amount of the brown sugar filling in the center. Fold the dough around the filling and roll back into a ball.

Place cookies on the prepared baking sheet and bake for 10-12 minutes, or until the edges are set. Let cool on the baking sheet for a few minutes before transferring to a wire rack.

Make the Glaze: In a small bowl, whisk together powdered sugar, cinnamon, melted butter, and milk until smooth.