Soft and chewy Brown Sugar Pop Tart Cookies are filled with a gooey brown sugar-cinnamon center and topped with a vanilla glaze—just like the childhood favorite, reinvented as a bakery-style cookie.
Filling:
½ cup brown sugar
1 tsp cinnamon
1 tbsp all-purpose flour
2 tbsp melted butter
Cookie Dough:
¾ cup unsalted butter, softened
½ cup granulated sugar
¼ cup brown sugar
1 egg + 1 egg yolk
1 ½ tsp vanilla extract
2 ¼ cups all-purpose flour
½ tsp baking soda
¼ tsp baking powder
¼ tsp salt
Glaze:
1 cup powdered sugar
2 tbsp milk or cream
½ tsp vanilla extract
Mix filling ingredients into a paste. Set aside.
Cream butter and sugars until fluffy. Add egg, yolk, and vanilla.
Mix in dry ingredients until soft dough forms. Chill 30 minutes.
Scoop 2 tbsp dough, flatten, add filling, top with another disk, and seal.
Bake at 350°F for 10–12 minutes. Cool completely.
Drizzle with glaze and let set before storing.
Chill dough to prevent spreading.
Don’t overfill center.
Freeze dough balls for future baking.