Description

These chewy, gooey cookies capture the nostalgic flavor of brown sugar cinnamon pop tarts with a homemade twist. Soft, buttery dough is filled with a sweet cinnamon-brown sugar center and finished with a classic glaze—perfect for sharing or satisfying a sweet snack craving.

Ingredients

Scale

2 1/4 cups all-purpose flour
1/2 teaspoon baking soda
1/2 teaspoon salt
3/4 cup unsalted butter, softened
1 cup packed light brown sugar
1/4 cup granulated sugar
1 large egg, room temperature
2 teaspoons pure vanilla extract
1/3 cup packed dark brown sugar
2 tablespoons ground cinnamon
2 tablespoons unsalted butter, melted
Pinch of salt
1 cup powdered sugar
2–3 tablespoons milk (any variety)
1/2 teaspoon vanilla extract

Instructions

Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
In a medium bowl, whisk together flour, baking soda, and salt. Set aside.
In a large bowl, beat softened butter, brown sugar, and granulated sugar with a mixer on medium speed until light and fluffy (2-3 minutes).
Beat in egg and vanilla extract until fully combined.
Gradually add the flour mixture to the butter mixture, mixing just until the dough comes together. Do not overmix.
If dough feels too sticky, chill for 20 minutes.
In a small bowl, stir together dark brown sugar, cinnamon, melted butter, and a pinch of salt to make the filling.
Scoop about 2 tablespoons of dough and flatten into a disk. Add 1/2 teaspoon of the brown sugar filling to the center, then fold the dough around it to seal. Roll gently to form a ball.
Place cookie balls 2 inches apart on the prepared sheet. If dough is soft, chill tray for 10 minutes.
Bake for 10-12 minutes, until edges are golden and centers look just set.
Let cookies sit on the sheet for 5 minutes, then transfer to a wire rack to cool completely.
In a bowl, whisk powdered sugar, milk, and vanilla until smooth to make the glaze. If too thick, add a splash more milk.
Drizzle or spread glaze over cooled cookies. Let glaze set for 15 minutes before serving.

Notes

Chill dough for thicker cookies and to prevent spreading. Seal the filling well to avoid leaks. Use gluten-free flour for a GF version, or coconut oil for dairy-free. Glaze consistency should be thick enough to drizzle but not runny. Store cookies in an airtight container for up to 4 days or freeze for up to 2 months.

Prep Time: 20 minutes
Cook Time: 12 minutes
Category: Dessert
Cuisine: American

Nutrition

Serving Size: 1 cookie (about 40g)
Calories: 185
Sugar: 16
Sodium: 90
Fat: 8
Saturated Fat: 5
Carbohydrates: 28
Fiber: 1
Protein: 2

Keywords: brown sugar, pop tart cookies, cinnamon, homemade cookies, sweet snack, dessert, easy cookie recipe, nostalgic, glaze, chewy cookies