These brown sugar cinnamon pop tart cookies take all the nostalgic flavor of your favorite toaster pastry and transform it into a soft, buttery cookie. Each cookie is filled with chewy brown sugar cinnamon filling, topped with a sweet cinnamon glaze, and tastes like a brown sugar cinnamon pop tart!
With a chewy sugar cookie base, sweet and spiced filling, and smooth cinnamon icing, these cookies are cozy, sweet, and irresistible. They're perfect for fall baking, adding to your Christmas cookie box, or simply for when you're craving something extra special.
We love stuffed cookies here at The Cozy Plum, so try these baklava cookies, coffee cake cookies, PBJ cookies, or fluffernutter cookies for more surprises!
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Why You'll Love This Recipe
Pop-Tart nostalgia - it has the exact cinnamon brown sugar filling and icing flavor, just in cookie form!
Soft and chewy texture - these cookies stay ultra soft for days right on the countertop!
Bakery-style look - they're perfectly round with a ribbon of filling and topped with that signature cinnamon icing on every cookie.
Ingredients
- Unsalted butter. Used in both the cookie dough base and melted into the filling.
- Brown sugar. This gets mixed with loads of cinnamon and butter to create that classic chewy pop tart filling.
- Cornstarch. Gets added to the filling to keep it chewy and stabilized rather than melting in to the dough.
- Eggs. Three egg yolks are used in the cookie dough to keep it rich and chewy without adding extra moisture.
- Cinnamon. Loads of ground cinnamon is mixed into the filling and the icing
- Powdered sugar. The base of the cinnamon icing used to go on top of the cookies.
See recipe card for full ingredients list and quantities.
Substitutions and Variations
- Add a touch of nutmeg or cardamom to the filling or glaze for an extra kick of spice.
- Use maple syrup instead of water in the glaze for a cozy fall flavor.
- Add finely chopped nuts to the cinnamon filling for a crunch (like in these baklava cookies).
- Make them mini! Use 1.5 tablespoons of dough and ½ teaspoon of filling for tinier, bite-sized cookies. Reduce the bake time by roughly half.
How to Make This Recipe
One: Mix together the ingredients for the cinnamon brown sugar filling until combined.
Two: Measure out 1 teaspoon pieces and roll them into balls.
Three: Cream together the butter and sugars until smooth.
Four: Add in the egg yolks and mix to combine. Scrape down the sides.
Five: Gently beat in the dry ingredients and finish bringing it together with a rubber spatula.
Six: Measure out 3 tablespoon pieces of dough, and flatten them out using your palm.
Seven: Add a dollop of the cinnamon sugar filling to the center of the dough.
Eight: Gently close the dough around the filling and seal.
Hot tip! If the cinnamon sugar balls get hard, re-squeeze them in your hands to soften, then form them into a ball again before adding to the dough.
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Nine: Roll the dough between your hands until smooth.
Ten: Gently press down on the cookie dough balls with your hand or the bottom of a cup until about 1cm thick. Bake and cool.
Eleven: Mix together the ingredients for the cinnamon icing.
Twelve: Spoon on top of the cooled cookies. Let the icing set before enjoying.
Expert Tips
- Measure the flour using a digital scale. Adding too much flour to the dough will cause it to be crumbly and crack during baking.
- If the cinnamon sugar filling balls feel very firm, squeeze them in your palm to soften, then re-roll. Hard balls won't flatten properly in the cookie when pressed before baking.
- Don't overbake! There isn't much cookie dough around the filling, so it doesn't need a ton of bake time. Overbaking will dry them out.
- Bake one sheet of cookies at a time to ensure even baking.
- Scoot the cookies as soon as they come out of the oven to sure up the sides. This helps to make sure the icing doesn't fall off, too!
- Make sure the icing isn't too thin or it won't set up nicely.
Testing Notes
- This is a foolproof sugar cookie dough used in my other stuffed cookie recipes. It easily holds a variety of fillings and is nice and pliable (so long as you measure the flour correctly).
- Adding cornstarch to the filling keeps it chewy and stabilized. No cornstarch had the filling melting into the dough. Flour made the filling hard and crumbly. Cornstarch kept it just right.
- I found that the butter in the filling hardened up since I've been testing during cold months while my house is pretty chilly. This hadn't happened with my other stuffed cookies (tested during summer months), so was a good realization that I needed to reshape the balls to ensure they flattened nicely when pressed down.
- Without scooting the cookies, the center filling wasn't as prominent when you bit in, and the icing fell off the sides. I'd highly recommend reshaping them quickly as soon as they come out of the oven so they have a nice "shelf" to hold the icing.
Recipe FAQs
Yes, the dough can be refrigerated (tightly covered) for 24 hours. Just let it come to temperature for 15-30 minutes before scooping and shaping.
Yes! Freeze the baked cookies (with the glaze) in a sealed container for up to 2 months. Thaw at room temperature before enjoying.
That's ok! Try to roll the dough evenly around the center, but some of them may get a bit wonky. If anything leaks out, it will just caramlize and add a bit of extra flavor.
Sure, but the glaze is what really gives it that true "pop tart" finish, so I highly recommend it!
Storage
Room temperature: store the cookies in an airtight container for 4 days.
Refrigerator: keep for up to a week. Bring to room temperature before serving.
Freezer: freeze glazed or unglazed cookies in an airtight container for up to two months. Layer with parchment paper to prevent sticking.
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What to Know When Cooking with The Cozy Plum
- All recipes are created with Diamond Crystal kosher salt, the least salty variety of kosher salt. If using Morton's, you'll need to cut the amount of salt in half as it's 2x as salty. This will be the same for sea salt. Please do not use table salt.
- Switch between Cups vs Metric using the toggle on the recipe card. Baking by weight using a digital scale will always produce the most accurate results.
- Scale the recipe using the '1X' '2X' '3X' buttons on the recipe card. Note that this does not make an adjustment for baking times, only quantities.
📖Recipe
Brown Sugar Cinnamon Pop Tart Cookies
Equipment
- Stand mixer with paddle attachment, or handheld mixer
Ingredients
Cinnamon Filling
- ¼ cup unsalted butter melted
- 5 tablespoons light brown sugar packed
- 3 teaspoons ground cinnamon
- ⅓ cup cornstarch
- ¼ teaspoon kosher salt
Cookie Dough
- ½ cup unsalted butter room temperature
- ½ cup light brown sugar
- ¼ cup granulated sugar
- 2 teaspoons vanilla paste or extract
- 3 large egg yolks room temperature
- 2 cups all-purpose flour
- ½ teaspoon baking powder
- ½ teaspoon baking soda
- ½ teaspoon kosher salt
Glaze
- 1 cup powdered sugar
- 1 teaspoon ground cinnamon
- ¼ teaspoon vanilla extract
- 1-2 tablespoons water
Instructions
Cinnamon Filling
- In a bowl, mash together the melted butter, brown sugar, cinnamon, cornstarch and salt until completely combined. Measure out the mixture into ½ tablespoon pieces, roll into a ball, then add to a parchment-lined plate, and set aside.¼ cup unsalted butter, 5 tablespoons light brown sugar, 3 teaspoons ground cinnamon, ⅓ cup cornstarch, ¼ teaspoon kosher salt
- Note: keep it in a relatively warm place so the butter doesn’t harden.
Cookie Dough
- In the bowl of a stand mixer fitted with the paddle attachment (or with a hand mixer), cream together the butter, sugars, and vanilla on medium-high speed for 5 minutes until light and fluffy. Scrape down the sides.½ cup unsalted butter room temperature, ½ cup light brown sugar, ¼ cup granulated sugar, 2 teaspoons vanilla paste or extract
- Add the egg yolks and beat on medium speed for another two minutes. Scrape down the sides again.3 large egg yolks
- Whisk together the flour, baking powder, baking soda, and salt, and add to the creamed ingredients. Mix on low until just combined. Use a rubber spatula to scrape down the sides and mix in any leftover dry ingredients by hand.2 cups all-purpose flour, ½ teaspoon baking powder, ½ teaspoon baking soda, ½ teaspoon kosher salt
Assembly
- Preheat the oven to 350℉ and line two large cookie sheets with parchment paper.
- Using a 3 tablespoon cookie scoop, scoop the cookies and place six onto each cookie sheet. Flatten out each piece of cookie dough with your hands, then add a dollop of the cinnamon sugar filling.
- Note: if the cinnamon sugar balls become hard, squish them in between your fingers a few times to re-soften, then re-roll and add to the cookie dough.
- Fold the dough around the filling and roll in between your hands to smooth. Repeat with all cookies.
- Press each cookie down gently with your hand until 1cm thick.
- Bake one pan at a time for 8-10 minutes until the edges are set.
- Scoot the cookies immediately after they come out of the oven to sure up the sides, then cool completely on the pan.
- Whisk together the glaze, then spoon completely over the fully cooled cookies so it covers the top entirely.1 cup powdered sugar, 1 teaspoon ground cinnamon, ¼ teaspoon vanilla extract, 1-2 tablespoons water
- Let the glaze fully set before enjoying.
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