Make the Filling (2 minutes)
In a small bowl, mix brown sugar, cinnamon, melted butter, and flour until a thick paste forms.
Set aside.
Prepare the Cookie Dough (5 minutes)
Cream softened butter with brown sugar and granulated sugar until smooth and fluffy.
Add the egg and vanilla; mix until fully combined.
Add Dry Ingredients (2 minutes)
In a separate bowl, whisk flour, baking soda, cinnamon, and salt.
Slowly add the dry mixture to the butter mixture and mix until a soft dough forms.
Assemble the Cookies (5 minutes)
Scoop dough into balls, flatten slightly, and add ½–1 teaspoon of the filling in the center.
Fold the dough around the filling and roll into a smooth ball.
Bake (10–12 minutes)
Place cookie dough balls on a lined baking sheet and bake at 350°F (175°C) for 10–12 minutes, until edges are lightly golden and centers look soft.
Make the Glaze (1 minute)
Whisk powdered sugar, cinnamon, vanilla, and milk until smooth and pourable.
Glaze and Serve
Let cookies cool completely before drizzling or spreading the glaze on top—just like a Pop-Tart.