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Brown Sugar “Pop-Tart” Cookies

Brown Sugar "Pop-Tart" Cookies

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Soft, chewy cookies filled with a gooey brown sugar cinnamon center and topped with a sweet glaze, just like your favorite breakfast pastry.

Ingredients

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  • 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
  • ¼ cup dark brown sugar
  • 2 tablespoons unsalted butter softened
  • 1 tablespoon ground cinnamon
  • 1 ½ cups powdered sugar
  • ½ teaspoon kosher salt
  • ½ teaspoon ground cinnamon
  • 3 tablespoons almond milk or sub whole milk

Instructions

  1. Line a sheet pan with parchment paper. Set it aside.
  2. In a medium mixing bowl, whisk together the flour, baking soda, baking powder, cinnamon, and salt. Set this dry mixture aside.
  3. In the bowl of a stand mixer fitted with the paddle attachment, add the softened butter, room temperature coconut oil, maple syrup, and 1 ½ cups dark brown sugar.
  4. Mix on medium speed until the mixture is pale tan and fluffy, about 2-3 minutes.
  5. Add in the vanilla extract, large egg, and egg yolk to the wet mixture. Mix until everything is just combined.
  6. Slowly add the dry ingredients into the wet ingredients in increments, mixing on low speed until just combined. Do not overmix.
  7. Remove the paddle attachment, cover the bowl with clingwrap, and set the dough aside.
  8. In a small bowl, combine ¼ cup dark brown sugar, 2 tablespoons softened butter, and 1 tablespoon ground cinnamon.
  9. Mix these ingredients together until completely combined and smooth.
  10. Using a cookie scoop, scoop out 20 tablespoon-sized portions of cookie dough onto the prepared sheet pan.
  11. Top each dough ball with a small, ½ teaspoon amount of the cinnamon filling in the middle of the ball.
  12. With the remaining cookie dough, scoop another 20 portions directly atop the existing cookies, creating a sandwich.
  13. Using your fingers, gently press down atop each cookie to flatten it slightly.
  14. Transfer the baking sheet to the freezer and chill for at least one hour, or preferably overnight.
  15. Preheat your oven to 350℉ (175°C).
  16. Line two baking sheets with fresh parchment paper.
  17. Divide your chilled dough between each tray, leaving ample space between them. You may need to bake in batches.
  18. Transfer the baking sheets to the preheated oven and bake for 12-14 minutes, rotating the trays halfway through baking.
  19. Remove the cookies from the oven.
  20. Immediately bang each sheet pan firmly on the counter to flatten the cookies slightly. This helps create crinkly edges.
  21. Transfer the baked cookies to a wire rack to cool completely. Repeat with any remaining cookie dough.
  22. While the cookies are cooling, prepare the icing glaze.
  23. In a medium mixing bowl, add the powdered sugar, ½ teaspoon cinnamon, ½ teaspoon kosher salt, and almond milk.
  24. Whisk all icing ingredients together until smooth and totally combined.
  25. Once the cookies are entirely cool, add about 2 teaspoons of icing to the top of each cookie.
  26. Use a spoon to gently smooth the icing out, leaving about a 1-centimeter border around the edges.
  27. Allow the icing to set before storing the cookies.

Notes

Ensure your butter and coconut oil are softened to room temperature for the best creamy dough texture.
Do not skip the chilling step; it’s crucial for preventing cookie spread and achieving thick, chewy cookies.
Bang the hot baking sheet on the counter right after baking to get those perfectly flat, crinkled tops.
Measure flour by spooning it into the measuring cup and leveling it off for accuracy.