Brown Sugar Pop Tart Cookies

Instructions

1. Beat the softened butter, granulated sugar, and 1/2 cup of the light brown sugar together in a large mixing bowl on medium-high speed for about 2 to 3 minutes until light and fluffy. Add the room-temperature egg and 1 teaspoon of the vanilla extract, and beat again until smooth. In a separate bowl, whisk together the flour, baking powder, baking soda, salt, and 1 teaspoon of the ground cinnamon. Turn mixer to low and gradually add the dry ingredients to the wet ingredients, mixing just until a soft dough forms.
2. Cover the mixing bowl tightly with plastic wrap and let the dough chill in the refrigerator for at least 30 to 45 minutes to prevent spreading. Prepare your baking sheets by lining them with parchment paper or silicone mats.
3. In a small bowl, combine the remaining 1 cup of light brown sugar and the remaining 2 teaspoons of ground cinnamon. Drizzle in 1 tablespoon of melted unsalted butter and stir with a fork until it resembles wet sand. Divide and roll the mixture into 8 to 10 equal filling balls.
4. Remove chilled dough from the refrigerator. Portion out 3-tablespoon-sized balls of dough and flatten each into a thick disc. Place a cinnamon-sugar filling ball into the center of each disc, fold the edges of the dough over, and pinch the seams tightly to seal. Roll the stuffed dough between your hands to smooth and place on the prepared baking sheets, leaving 2 inches of space between each.
5. Preheat your oven to 350°F (175°C). Bake the cookies for 10 to 12 minutes until the edges are lightly golden but the tops still look slightly soft. Let the cookies rest on the hot baking sheet for 5 minutes before transferring them to a wire rack to cool completely.
6. Whisk together the powdered sugar, whole milk, and the remaining 1 teaspoon of vanilla extract until smooth but thick. Drizzle or spread a generous spoonful of glaze over the top of each cooled cookie, then immediately sprinkle with coarse brown sugar pearls. Let the glaze set completely for about 15 minutes before serving.