These brown sugar cinnamon Pop Tart cookies combine soft sugar cookies with a gooey cinnamon brown sugar filling and sweet cinnamon icing.

A close up of brown sugar cinnamon pop tart cookies on a cooling rack.

If you love brown sugar cinnamon Pop-Tarts, these cookies are about to become a new favorite. They take everything you love about the classic breakfast treat and turn it into a chewy, bakery-style cookie.

The cookies start with a tender sugar cookie dough that’s wrapped around a rich brown sugar cinnamon filling. Once baked, they’re finished with a simple cinnamon icing that sets into a sweet glaze on top. The combination of buttery cookie, warm cinnamon, and brown sugar makes these especially cozy for fall and the holiday season.

They’re a little more involved than your average cookie, but the extra step of adding the filling is completely worth it. Serve them with a cup of coffee, hot chocolate, or a cold glass of milk for the ultimate nostalgic treat.

Ingredients

For the Sugar Cookies

All-purpose flour: Ensure you measure your flour using the spoon and level method to avoid adding too much flour.
Baking powder and baking soda: Helps the cookies puff slightly while keeping them soft and tender.
Salt: Balances the sweetness and enhances the buttery flavor.
Unsalted butter: Use softened butter so it creams easily with the sugar. Unsalted butter gives you better control over the overall saltiness.
Granulated sugar: Gives the cookie base its classic sugar cookie flavor and helps create lightly crisp edges.
Egg: Adds moisture and helps bind the dough together.
Vanilla extract: Adds depth of flavor.

For the Brown Sugar Cinnamon Filling

Brown sugar: The key to that classic Pop-Tart-inspired filling. Light or dark brown sugar can be used; dark brown sugar will give you a deeper molasses flavor.
Ground cinnamon: Adds the warm cinnamon flavor that makes these cookies taste like the classic breakfast pastry.
Unsalted butter: Helps turn the brown sugar and cinnamon into a rich, spreadable filling.
All-purpose flour: Helps thicken the filling.
Milk: Adds moisture to the filling so it isn’t gritty.

For the Cinnamon Icing

Powdered sugar: Creates a smooth, sweet glaze that sets nicely on the cooled cookies.
Melted butter: adds richness and helps the icing firm up.
Milk: Thins the icing to the right consistency. Add it gradually so the icing doesn’t become too runny.
Ground cinnamon: Gives the glaze an extra pop of cinnamon flavor, similar to Pop Tarts.

Equipment

Stand mixer or hand mixer
Mixing bowls
Baking sheets
Measuring cups and spoons
Rubber spatula
Cookie scoop

An iced brown sugar cinnamon pop tart cookies.

Instructions

1. Make the cookie dough

Whisk together the flour, baking powder, baking soda, corn starch and salt in a medium bowl.

In the bowl of a stand mixer fitted with the paddle attachment, beat the softened butter and granulated sugar until light and fluffy, about 2–3 minutes. Add the egg and vanilla extract and mix until well combined.

Gradually add the dry ingredients to the wet ingredients, mixing just until a soft dough forms. Be careful not to overmix the dough.

Cover the dough and refrigerate for at least 1 hour.

2. Make the brown sugar cinnamon filling

While the dough chills, combine the brown sugar, cinnamon, softened butter, flour and milk in a small bowl. Mix until you have a thick, cohesive filling.

The filling should be soft enough to spread but firm enough to scoop and handle. If it feels too soft, refrigerate it for a few minutes.

3. Assemble the cookies

Preheat the oven to 350°F and line a baking sheet with parchment paper.

Using a one ounce cookie scoop (2 tablespoons), scoop a portion of cookie dough and flatten it into a small disc. Place a 1-2 teaspoons of the brown sugar cinnamon filling in the center, then cover with another 1/2 scoop of flattened dough.

Pinch the edges together to completely seal the filling inside, then gently roll the cookie between your hands to smooth the edges. Flatten slightly and place on the prepared baking sheet, leaving space between each cookie.

Repeat with the remaining dough and filling.

4. Bake

Bake the cookies for approximately 12-13 minutes, or until the edges are set and the centers still look slightly soft. The cookies will continue to set as they cool.

Allow the cookies to cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely.

5. Make the cinnamon icing

Whisk together the powdered sugar, cinnamon, butter, and milk until smooth. Start with a small amount of milk and add more as needed until you reach a thick but spreadable consistency.

Once the cookies are completely cooled, drizzle or spread the cinnamon icing over the tops. Allow the icing to set before serving.

A collage of six photos dipicting the filling, the cookie dough, adding the filling to a disc of cookie dough, covering with another piece of cookie dough, rolling into a flatten ball and placing on a baking sheet.

Tips

Don’t overbake the cookies. The centers should look slightly soft when you take them out of the oven. Over baking can result in a crispy cookie instead of a soft and chewy one.
Make sure the filling is completely enclosed. Any exposed filling can leak out while the cookies bake. Pinch the edges together well before rolling the dough smooth.
Chill the dough if it gets too soft. If the dough becomes difficult to work with while assembling the cookies, place it back in the refrigerator for 10–15 minutes.
Don’t make the filling too thick. A generous amount of filling is delicious, but using too much can make it difficult to properly seal the cookies.
Let the cookies cool before icing. If they’re still warm, the icing will melt and become too thin instead of creating a sweet glaze on top.

Substitutions

Dark brown sugar: Use dark brown sugar in the filling for a richer, more molasses-forward flavor.
Salted butter: Salted butter can be used in place of unsalted butter. If using salted butter, reduce or omit the additional salt in the cookie dough.
Extra cinnamon: Add a pinch of cinnamon to the cookie dough itself for even more cinnamon flavor.

An overhead shot of a cooling rack full of brown sugar cinnamon pop tart cookies.

More Cookie Recipes

If you make these Brown Sugar Cinnamon Pop Tart Cookies, be sure to leave a comment below and rate this recipe! If you snap a pic, be sure to tag me on Instagram @thechowdown! I love seeing your creations!

A close up of the cross section of a brown sugar cinnamon pop tart cookie.

Print Recipe