Pop Tart Cookies

These Brown Sugar Pop Tart Cookies are the ultimate nostalgic treat! Soft, chewy cookies are stuffed with brown sugar cinnamon filling and finished with a sweet cinnamon glaze for a cookie that tastes just like your favorite childhood snack!

Course Dessert

Cuisine American

Keyword pop tart cookies

Prep Time 30

Cook Time 10

Chill Time 30

Total Time 1 10

Servings -20 cookies

Calories 281kcal

Author Tawnie Graham of Kroll's Korner

Ingredients

Brown Sugar Cinnamon Filling

3/4 cup dark brown sugar, packed
1½ Tbsp. ground cinnamon
2 Tbsp. all-purpose flour
Pinch of kosher salt
4 Tbsp. unsalted butter, partially melted
1/2 tsp. vanilla extract

Cookies

1 cup unsalted butter, not quite room temperature (I usually have mine out on the counter just 10-15 minutes before mixing, no longer)
1 cup light brown sugar, packed
1/2 cup granulated sugar
2 large eggs, room temperature
2 tsp. vanilla extract
3 cups all-purpose flour
1½ Tbsp. cornstarch
1½ tsp. baking powder
1 tsp. baking soda
1 tsp. ground cinnamon
3/4 tsp. salt

Glaze

1½ cups powdered sugar
1/2 tsp ground cinnamon
1/2 tsp vanilla extract
1 Tbsp. light corn syrup
2-3 Tbsp. whole milk
Pinch kosher salt

US Customary - Metric

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Instructions

Make the filling: In a small bowl, stir together the brown sugar, cinnamon, flour, and salt. Add the melted butter and vanilla and stir until a thick, paste-like filling forms.
3/4 cup dark brown sugar, 1½ Tbsp. ground cinnamon, 2 Tbsp. all-purpose flour, Pinch of kosher salt, 4 Tbsp. unsalted butter, 1/2 tsp. vanilla extract
Portion and freeze: Scoop the filling into small portions, about 1/2 tablespoon each (you should have about ~18-20 little mounds). Place on a parchment-lined plate or baking sheet and gently flatten each into a small disc. Freeze for 15-20 minutes or just until frozen solid while you make the cookie dough. Start Timer
Make the cookie dough: Add the butter, brown sugar, and granulated sugar to the bowl of a stand mixer fitted with the paddle attachment. Cream on medium speed for 3-4 minutes Start Timer, scraping down the sides of the bowl as needed, until creamy. Add the eggs and vanilla and mix until combined.
1 cup unsalted butter, 1 cup light brown sugar, 1/2 cup granulated sugar, 2 large eggs, 2 tsp. vanilla extract

Check out my step-by-step for How To Cream Butter and Sugar for perfect baking results every time.

Add the dry ingredients: In a separate bowl, whisk together the flour, cornstarch, baking soda, baking powder, salt, and cinnamon.
3 cups all-purpose flour, 1½ Tbsp. cornstarch, 1½ tsp. baking powder, 1 tsp. baking soda, 1 tsp. ground cinnamon, 3/4 tsp. salt
Combine ingredients: Gradually add the dry ingredients to the wet ingredients and mix just until a thick cookie dough forms. Do not overmix.
Stuff the cookies: Portion the dough into ~2 tbsp. Scoop cookies. You need a slightly large dough ball so you can stuff with the filling. Working with one dough ball at a time, divide it roughly in half and flatten both pieces into discs. Use lightly floured hands if cookie dough is sticky. Place one chilled brown sugar filling disc in the center of one piece of dough. Top with the second piece and pinch the dough completely around the filling to seal. Roll gently into a ball, making sure no filling is exposed. Repeat with the remaining cookies. You should have ~18-20 cookies.
Chill: Place the stuffed cookie dough balls on a parchment-lined baking sheet and refrigerate for 30 minutes. Start Timer Meanwhile, preheat the oven to 350°F and line baking sheets with parchment paper or silicone baking mats.
Bake: Arrange the cookies several inches apart on the prepared baking sheets. I usually don’t bake more than 6 at a time. Use your fingers to shape the dough so it’s nice and tall, almost like a cylindrical shape. I like to do this to keep the cookie thicker. Bake for ~10-11 minutes Start Timer, or until the edges are set and lightly golden but the centers still look soft and slightly underbaked. Keep other cookies refrigerated between batches. Immediately after removing them from the oven, use a large round cookie cutter to "cookie scoot" the cookies into perfectly round shapes. Cool on the baking sheet for 10 minutes before transferring to a wire rack. Cool completely before glazing.
Make the glaze: Whisk together the powdered sugar, cinnamon, vanilla, corn syrup, 2 tablespoons milk, and salt until smooth. Add additional milk as needed until the glaze is thick but spreadable.
1½ cups powdered sugar, 1/2 tsp ground cinnamon, 1/2 tsp vanilla extract, 1 Tbsp. light corn syrup, 2-3 Tbsp. whole milk, Pinch kosher salt
Decorate: Spoon or spread the glaze over the completely cooled cookies, leaving a small border around the edges. Allow the glaze to set before serving. BEST COOKIES EVER! enjoy!

Notes

Freeze the filling: Make sure the brown sugar filling is completely frozen solid before stuffing the cookies. This makes it much easier to work with and helps keep the filling from leaking out while baking.
Shape the cookies before baking: Right before baking, use your fingers to gently shape the stuffed dough balls into a tall, slightly cylindrical shape. This helps the cookies stay thicker as they bake.
Keep the dough chilled: Keep the unbaked cookies refrigerated between batches so the dough stays cold and the cookies don't spread too much in the oven.
Let cookies cool before adding glaze: Make sure to let the cookies cool completely before drizzling with the glaze! If they’re still warm, the glaze will melt right off.
To store: Store in a sealed container at room temperature for up to 5 days.
Freeze baked cookies: Allow to cool completely and place in freeze safe baggie for up to 3 months.

Recipe is inspired by Sugar Spun Run & What Molly Made.

Nutrition