Pop Tart Cookies
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If you love brown sugar cinnamon Pop-Tarts, you are going to LOVE these cookies! They take all those nostalgic cinnamon-sugar flavors and turn them into a soft, chewy, bakery-style cookie with a sweet filling in the middle.
They are a little more involved than some of my other recipes since you’re stuffing each one with the brown sugar cinnamon filling, but I promise the extra step is SO worth it. Once they’re baked and topped with that sweet cinnamon glaze, they really do taste like a homemade version of everyone’s favorite Pop-Tart!
These are such a fun cookie to make for fall, holidays, or anytime you’re craving that classic brown sugar cinnamon combination. And if you’re a Pop-Tart fan, I have a feeling these won’t last long!
And if you’re craving the real thing, be sure to try my Brown Sugar Pop Tarts or Homemade Strawberry Pop Tarts.
Table Talk with Tawnie
I am kind of a cookie queen at this point…dontcha think?! Every day my daughter comes home from school asking what cookies I made that day as if I just spend all my time making cookies 😆 But these cookies were so much fun to create. Brown sugar pop tarts are my favorite pop tart flavor so naturally I had to make them into a cookie version! They’re a great holiday cookie and something a little unique for your dessert spread this year! I know you’ll love these
- All-purpose flour: As always, it’s essential to make sure you’re using the spoon-and-level method to measure your flour when baking. Too much flour can result in drier, harder cookies, which you don’t want with these!
- Cornstarch: Cornstarch is key to giving these cookies that delectably soft center that’s just to die for. It also helps to keep the cookies thick and chewy.
- Brown sugar: Use dark brown sugar for the filling and light brown sugar for the cookie dough. The dark brown sugar gives the filling a deeper, richer flavor, while light brown sugar keeps the cookie dough balanced.
- Butter: For the filling, you’ll want partially melted butter so it mixes easily with the other ingredients. For the cookie dough, use softened butter that’s not quite room temperature. I usually let mine sit on the counter for just 10–15 minutes before mixing.
- Light corn syrup: Helps create a smooth, glossy icing. It also helps the icing set and harden properly, so the cookies can be stacked without sticking together. Don’t worry, light corn syrup is not the same as high fructose corn syrup!
Step by Step Directions
(For the full recipe, scroll down to the recipe card below)
Make the filling
Mix the brown sugar, cinnamon, flour, salt, melted butter, and vanilla until a thick paste forms. Scoop into little portions, flatten into discs, and freeze on a parchment-lined sheet until solid.
Cream the butter, brown sugar, and granulated sugar until creamy. Mix in the eggs and vanilla. In a separate bowl, whisk together the dry ingredients, then gradually add them to the wet mixture and mix just until a thick dough forms. Be careful not to overmix.
Portion the dough into ~2-tablespoon balls. Divide each ball in half and flatten into discs. Place a chilled filling disc in the center of one piece, top with the second, and pinch the dough completely around the filling to seal. Roll into a smooth ball with no filling exposed. Chill the stuffed dough balls for 30 minutes.
Bake
Bake for ~10-11 minutes. 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, then transfer to a wire rack and let cool completely.
Glaze & enjoy!
Whisk together the glaze ingredients. Spoon the glaze over the completely cooled cookies and allow the glaze to fully set. Serve and ENJOY!!
Expert Tips
- 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.
- Spoon and level flour: Spoon the flour into your measuring cup and be sure it’s leveled. Do not scoop the flour out of the container/bag with your measuring cup because you could end up with 50% more than you need. Spoon and level by using a spoon to scoop the flour into the measuring cup and use the back of a knife to level off the top of it.
- Don’t over-mix: Be careful not to over-mix. Mix the wet and dry ingredients just until no flour streaks remain.
- 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.
- Perfectly round cookies: Use any round object slightly larger than the cookies, like a large round cookie cutter, biscuit cutter, or even the open top of a wide glass or mug. Place the ring around the warm cookie and gently swirl or “scoot” the cookie in small circles. The edges will nudge into a perfect round shape. Be sure to do this while the cookies are still hot and pliable, usually within the first 30 seconds of coming out of the oven!
- Don’t overbake: Bake these cookies just until the edges are set, but the centers still look slightly soft and underbaked. The cookies will continue to set as they cool.
- 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.
How To Properly Cream Butter and Sugar
Learn How To Cream Butter and Sugar the right way with this easy step-by-step guide. Discover the best butter temperature, mixing tips, and common mistakes to avoid for perfect baking results every time.
Storage / Freezing
- 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.
- Freeze cookie dough: Once you make the cookie dough, roll it into balls and freeze for up to 2 months. Once you’re ready to bake them, allow them to reach room temperature, then bake according to the recipe directions and glaze as instructed.
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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
- 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
Last step! If you make this, please leave a review and rating letting us know how you liked this recipe! This helps our business thrive & continue providing free recipes.
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
- 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.
Nutrition Information
Nutritional information is provided as a courtesy and is automatically calculated. It should only be construed as an estimate rather than a guarantee. Ingredients can vary and Kroll’s Korner can’t make any guarantees to the accuracy of this information.
📸 Photos by Megan McKeehan of The Broke Girl Table
