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Brown Sugar Cinnamon Pop Tart Cookies

Remember that warm, cozy smell of brown sugar cinnamon Pop-Tarts popping out of the toaster? That sweet mix of cinnamon and sugar that filled the kitchen and made you forget you were running late for the bus? These Brown Sugar Cinnamon Pop Tart Cookies bring all that nostalgic goodness back—only this time, in soft, chewy cookie form. With a buttery dough, gooey cinnamon filling, and a drizzle of icing on top, they’re like a warm hug from your childhood—straight from the oven.

I found this recipe at whatmollymade.com (thanks Molly!) and made just a couple of adjustments to the recipe. I love these cookies and you will too! They really do taste just like Pop-Tarts (without any preservatives). Enjoy!

Brown Sugar Cinnamon Pop Tart Cookies on a cutting board.

Brown Sugar Cinnamon Pop Tart Cookies

Imagine everything you love about these classic toaster treats—warm cinnamon, rich brown sugar, and a sweet glaze—all wrapped up in a soft, buttery cookie. These Brown Sugar Cinnamon Pop Tart Cookies are a gourmet version of your childhood favorite!
Prep Time 20 minutes
Cook Time 24 minutes
Chilling Time 15 minutes
Total Time 59 minutes
Course Dessert

Ingredients
  

Cookies

  • 3 3/4 cups cake flour (see notes for substitute)
  • 2 Tbsp corn starch
  • 2 Tbsp bread flour
  • 1 tsp baking soda
  • 1 1/2 tsp baking powder
  • 1 cup salted butter, softened (2 sticks)
  • 1 cup light brown sugar (packed)
  • 1/2 cup granulated sugar
  • 2 eggs (room temp)
  • 1 tsp vanilla extract

Brown Sugar Filling

  • 5 Tbsp butter (melted)
  • 3/4 cup light brown sugar (packed)
  • 2 Tbsp cake flour
  • 1 tsp cinnamon

Brown Sugar Cinnamon Glaze

  • 1 cup powdered sugar
  • 1 Tbsp milk
  • 1 Tbsp corn syrup
  • 1 tsp vanilla extract
  • 1/2 tsp cinnamon

Instructions
 

  • Line 2 cookie sheets with parchment paper and set aside.

Make the Dough

  • Add dry ingredients to a medium size bowl and whisk gently until thoroughly combined.
  • Add the butter, sugar, and brown sugar to the bowl of a stand mixer fitted with the paddle attachment. Beat on medium speed until well combined. Add eggs, one at a time, mixing just until combined. Add vanilla and mix until combined.
  • Add dry ingredients to the wet ingredients in 3 parts. Mix on low speed until combined. Stop to scrape sides of bowl as needed.

Make the Filling

  • Add the melted butter, brown sugar, cake flour, and cinnamon to a medium bowl and stir until combined.

Assemble the Cookies

  • Scoop the dough with a medium-sized ice cream scoop and place on cookie sheet (8 cookies per sheet).
  • Break each dough ball in half and create a well in the middle of one half to hold the filling.
  • Add a heaping teaspoon of filling to the well and cover with the other half of the dough.
  • Pinch all the way around the edges to seal.
  • Shape into a ball and place back on the cookie sheet. Repeat for remaining cookies.
  • Preheat oven to 350° F. Refrigerate cookies while oven in preheating.
  • Bake for 12 minutes until the top is set and the edges are golden brown. Turn the tray half way through.
  • Cool on the baking sheet for about 10 minutes, then transfer to a wire rack to cool completely.

Make the Icing

  • Whisk together the powdered sugar, cinnamon, corn syrup, milk, and vanilla. Stir until smooth.
  • Spoon the icing on cooled cookies, spreading it to the edges. Allow icing to set until firm.

Notes

If you don’t have cake flour, you can use all-purpose flour and corn starch. Replace 2 Tbsp flour with 2 Tbsp corn starch per cup of flour. For this recipe, remove 7 1/2 Tbsp flour (from the 3 3/4 cups all-purpose flour) and add equal amount of corn starch. This doesn’t include the corn starch called for in the recipe ingredients.
I use salted butter in all my recipes. If you choose to use unsalted butter, add 1 tsp salt to dry ingredients.
Many recipes say to beat butter and sugar until light and fluffy. I’ve found that doing that encourages cookies to spread while baking, and I don’t want wide, flat cookies. I only mix the butter and sugar until it’s combined.
Baking time will vary by oven. Watch your first batch carefully and adjust time as necessary.
Refrigerating the cookies before baking will help reduce spread.
The scoop I use holds about 2.7 oz. of dough.
Keyword cinnamon, cookies, pop tart, brown sugar