1. Make the filling
In a bowl, mix brown sugar, cinnamon, flour, and melted butter until it resembles a thick paste. Set aside.
2. Make the cookie dough
Beat softened butter, brown sugar, and granulated sugar until creamy.
Mix in eggs and vanilla.
In a separate bowl, whisk together flour, baking soda, baking powder, and salt.
Gradually add dry ingredients to wet mixture until dough forms. Chill for 30 minutes.
3. Assemble cookies
Preheat oven to 350°F (175°C) and line baking sheets with parchment paper.
Scoop about 2 tablespoons of dough, flatten into a disc.
Place 1–2 teaspoons of cinnamon filling in the center.
Top with another disc of dough and seal the edges. Flatten slightly.
Repeat with remaining dough.
4. Bake
Bake 10–12 minutes, until edges are golden but centers are still soft.
Let cool completely before glazing.
5. Glaze
Whisk together powdered sugar, cinnamon, milk, and vanilla until smooth and spreadable.
Spread glaze over cooled cookies. Allow to set before serving.
✨ These taste just like the classic Brown Sugar Cinnamon Pop Tarts but in soft, gooey cookie form!
