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These Brown Sugar “Pop-Tart” Cookies are a decadent take on the breakfast pastry we all grew up loving! Perfectly buttery cookies with a cinnamon center, topped with a simple icing, these will take you right back to your childhood favorite.

Brown Sugar "Pop-Tart" Cookies on a sheet pan.

These are a decadent and festive take on an all-time holiday classic, Brown Sugar Cinnamon Pop-Tarts. With a brown sugar cookie base, warm and buttery cinnamon layer, and a spiced glaze, these are a labor of love but absolutely worthy of adding to your holiday cookie repertoire! And if you are looking for that classic Strawberry Pop-Tart taste, try my Pop-Tart Cookie Bars.

I know it’s hard to wait to bake a batch of cookies, but these Brown Sugar “Pop-Tart” Cookies really need a chill in the freezer to hold their shape. We ask for at least 1 hours in the freezer, but overnight is even better to get the flavors to really develop. You can also make these weeks in advance, store in a gallon zip-top bag, and bake them off when you please.

Brown Sugar “Pop-Tart” Cookies Ingredients:

  • Gluten-Free 1:1 Flour (Or All-Purpose Flour)
  • Baking Soda
  • Baking Powder
  • Cinnamon
  • Salt
  • Unsalted Butter
  • Coconut Oil
  • Maple Syrup
  • Dark Brown Sugar
  • Vanilla Extract
  • Egg
  • Powdered Sugar
  • Almond Milk or Whole Milk
Brown Sugar "Pop-Tart" Cookies stacked on a pan.

Brown Sugar “Pop-Tart” Cookies Recipe Step-by-Step:

Step One: mix the dry ingredients

After you line a sheet pan with parchment paper, start the dough. Whisk together the flour, baking soda, baking powder, cinnamon, and salt in a medium mixing bowl. Set aside.

Step Two: mix the wet ingredients then combine

Next, in the bowl of a stand mixer fitted with the paddle attachment, add the butter, coconut oil, maple syrup, and dark brown sugar. Mix until fluffy. Add in the vanilla, egg, and egg yolk. Mix until combined. Once combined, slowly add the dry ingredients into the wet, mixing on low until just combined. Remove the paddle attachment, cover the bowl with clingwrap, and set aside.

Brown Sugar "Pop-Tart" Cookie dough in mixing bowl.

Step Three: Make the Cinnamon Filling

In a small bowl, mix together the brown sugar, butter, and cinnamon until totally combined and smooth.

Cinnamon filling in a small bowl.

Step Four: Assemble the Cookies

Scoop out 20 tablespoon-sized cookies onto the prepared sheet pan. Top each of the dough balls with a small, ½ teaspoon of the cinnamon filling in the middle of the ball. Finally, with the remaining cookie dough, scoop another 20 directly atop the existing cookies, making a sandwich. Using your fingers, gently press down atop each cookie to flatten. The cinnamon layer may squeeze out the sides a bit, but it should mostly remain within the cookie.

Brown Sugar "Pop-Tart" Cookies being assembled on sheet pan.

Step Five: Chill the Cookies

Transfer the baking sheet to the freezer and chill for at least an hour, or overnight.

Step Six: Bake the Cookies

Preheat the oven to 350℉. Bake the cookies for 12 to 14 minutes, rotating the pans halfway through. Remove from oven and follow tips below for perfectly flattened and round cookies!

Step Seven: Make the Frosting

While the cookies cool completely, make the frosting. In a medium mixing bowl, add the powdered sugar, cinnamon, kosher salt, and almond milk. Whisk until smooth and totally combined.

Step Eight: Frost, Set, Enjoy!

Add about 2 teaspoons of icing to each cookie, using a spoon to smooth the icing out, leaving about a 1-centimeter border around the edges. Allow to set before storing!

Brown Sugar "Pop-Tart" Cookies on a sheet pan.

Brown Sugar “Pop-Tart” Cookies Recipe FAQs:

Can I use almond flour in this recipe?

Gluten-free 1:1 flour or all-purpose flour is needed in this recipe!

Do I really need to let the dough chill for an hour?

YES! You absolutley need to let the dough rest for atleast 1 hour. This helps the dough keep its shape and ensures that the cinnamon filling will not pour out once baked. You also need to let them cool completely before frosting them!

Could I make the dough in advance?

Absolutely! Because you need to let the dough chill, you can make the dough up to a week in advance and bake once you are ready. Once the dough is frozen on the sheet pan, you can transfer the dough to a gallon zip-top bag for easier storage.

hOW DO YOU MAKE A PERFECTLY ROUND COOKIE?

Place a ramekin or cup over the still-warm cookies while on the sheet pan. Swirl the ramekin (or cup) around and you will be left with a perfectly round cookie.

I cannot wait for y’all to make these Brown Sugar “Pop-Tart” Cookies! Comment below once you try them!

Looking for more baking ideas?

Lofthouse Cookie Bars

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Brown Sugar "Pop-Tart" Cookies on a sheet pan.
4.95 from 17 votes

Brown Sugar “Pop-Tart” Cookies

Gluten-Free

Ingredients 

For the Dough:

  • 2 ½ cups gluten free 1:1 flour sub All Purpose flour if needed
  • ¾ teaspoons baking soda
  • 1 teaspoon baking powder
  • ½ teaspoon ground cinnamon
  • ¾ teaspoon kosher salt
  • 1 ½ sticks unsalted butter softened
  • ¼ cup coconut oil room temperature (regular coconut oil, not liquid)
  • 1 tablespoon maple syrup
  • 1 ½ cups dark brown sugar
  • 2 teaspoons vanilla extract
  • 1 large egg plus 1 egg yolk room temperature

For the Cinnamon Filling:

  • ¼ cup dark brown sugar
  • 2 tablespoons unsalted butter softened
  • 1 tablespoon ground cinnamon

For the Icing Glaze:

  • 1 ½ cups powdered sugar
  • ½ teaspoon kosher salt
  • ½ teaspoon ground cinnamon
  • 3 tablespoons almond milk or sub whole milk

Instructions 

  • Line a sheet pan with parchment paper. Set aside.

Make the Dough:

  • In a medium mixing bowl, whisk together the flour, baking soda, baking powder, cinnamon, and salt. Set aside.
  • In the bowl of a stand mixer fitted with the paddle attachment, add the butter, coconut oil, maple syrup, and dark brown sugar. Mixing on medium, cream together until pale tan and fluffy, 2-3 minutes. Add in the vanilla, egg, and egg yolk. Mix until combined.
  • Working in increments, slowly add the dry ingredients into the wet, mixing on low until just combined. Remove the paddle attachment, cover the bowl with clingwrap, and set aside.

Make the the Cinnamon Filling:

  • In a small bowl, mix together the brown sugar, butter, and cinnamon until totally combined and smooth.

Assemble and Chill:

  • Using a cookie scoop, scoop out 20 tablespoon-sized cookies onto the prepared sheet pan. Don’t worry if the sheet looks crowded, this is only to chill them, not to bake. Top each of the dough balls with a small, ½ teaspoon of the cinnamon filling in the middle of the ball. Finally, with the remaining cookie dough, scoop another 20 directly atop the existing cookies, making a sandwich.
  • Using your fingers, gently press down atop each cookie to flatten. The cinnamon layer may squeeze out the sides a bit, but it should mostly remain within the cookie.
  • Transfer the baking sheet to the freezer and chill for at least an hour, or overnight.

Bake the Cookies:

  • Preheat the oven to 350℉. Line two baking sheets with parchment paper.
  • Divide your dough between each tray, leaving ample space between them. You may need to bake in batches! Transfer to the oven and bake for 12-14 minutes, rotating the trays halfway through.
  • Remove from the oven, and bang the sheet pan on the counter to flatten the cookies slightly. See note for an extra tip for perfectly shaped cookies! Transfer the cookies to a wire rack and repeat with the remaining cookies.

Make the Icing Glaze and Frost:

  • Allow the cookies to cool entirely. While the cookies are cooling, mix together the icing. In a medium mixing bowl, add the powdered sugar, cinnamon, kosher salt, and almond milk. Whisk until smooth and totally combined.
  • Add about 2 teaspoons of icing to each cookie, using a spoon to smooth the icing out, leaving about a 1-centimeter border around the edges. Allow to set before storing.

Notes

For Perfectly Shaped Cookies:  If you’d like to be a perfectionist with your cookies, try this trick! Place a ramekin or cup over the still-warm cookies while on the sheet pan. Swirl the ramekin (or cup) around and you will be left with a perfectly round cookie.

Nutrition information is automatically calculated, so should only be used as an approximation.

Additional Info

Photography and styling by Eat Love Eats.



Welcome! I’m Alex.

I’m a food lover sharing healthy, simple, delicious, recipes from my kitchen to yours. Here you’ll find lots of Whole30, lots of healthy, and a little indulgence here and there because…it’s all about balance y’all!


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Recipe Rating




36 Comments

  1. 5 stars
    DELICIOUS! I finally made these this week and they are perfect. Followed the recipe to a T and didn’t have any issues. They definitely do get larger, but I left plenty of space between them and didn’t have any issues – and they almost all came out perfectly round. I brought some to work and everybody loved them too. I think they were even better the next day – so soft and chewy!

  2. 4 stars
    A Christmas hit! I trust Alex so much that i chose to make these for the first time to take to a Christmas Eve event with boyfriend’s family. And they received rave reviews, notably, “The dough is so soft!”.

    I subbed lactaid whole milk in the icing, and it didn’t harden, so I kept them in the fridge. Transporting wasn’t easy because of this so I’d like to keep experimenting here or i’ll try some without frosting (this is actually how I prefer the original pop-tarts).

    My first batch also spread significantly but this was okay because i was afraid the cookies would be small. The only thing i can think of is the first pan with fresh out of the freezer, whereas the second had come closer to room temp while waiting to go in.

    I easily made 2 dozen. Used all-purpose flour.

    Happy Dinner Tonight Day!

  3. 5 stars
    You have restored my Christmas baking spirit! I had a couple of things not turn out, but decided to try these anyway. They turned out perfect and delicious! The directions were awesome and the tips spot on. Every recipe I have tried of yours turns out this way. Thank you!

  4. 5 stars
    I swear I measured my cookie balls and this made 35 complete cookies 🙈 Perhaps I beat the wet ingredients too long. Not complaining because these are delicious and perfect in every way. Found I had to add more powdered sugar to get the frosting the consistency it needed to be. Will definitely be making again!

  5. 5 stars
    These are amazing! I’ve already made them twice for Christmas gatherings! All my non GF/DF friends and family have raved about them! I have been gluten free for almost 11 years, and I cook or bake something from Defined Dish weekly (or daily) ❤️😂 thanks for all the wonderful recipes!

  6. 5 stars
    these are AMAZING and they were a huge hit with my family for our annual holiday bake afternoon. I’ll definitely be adding these to my annual round up!

  7. I’m absolutely in love with these!!!! As a late 90s baby I never had pop tarts so I can’t compare but these are delicious!! I’m making them for a second time, however my store didn’t have dark brown sugar. Would light brown sugar still yield the same outcome?

  8. Hi! What is the best flour to use for these cookies? I know you said 1:1 all purpose flour. But idk what that would be. Cassava? Almond?

  9. Hi, Alex! I’m a huge fan and love all of your recipes that I’ve made (which is a lot!) I just made these cookies and while they are DELICIOUS, they spread like crazy. Like, I put 6 on a large baking sheet and they all merged. Do you have any thoughts on what caused this? I’d love to make them again without them spreading. I’m confident I measured all ingredients correctly and didn’t make any substitutions.

    1. Kaitlin, I had the same experience! The first round all merged, then I put even fewer on the cookie sheet and baked them in 4 total batches.