These cinnamon roll cookies are what happens when a soft, chewy snickerdoodle meets the gooey, cinnamon-swirled center of a classic cinnamon roll—a delicious soft and chewy cookie base with a gorgeous cinnamon brown sugar ribbon throughout. After six rounds of testing (yes, six), I finally landed on the exact texture I wanted: lightly crisp edges, a tender and soft center, and ribbons of cinnamon sugar running through every bite. They’re rolled in cinnamon sugar for extra aroma and baked just until soft, making them dangerously easy to eat straight off the pan. They also make for INSANE ice cream cookie sandwiches – you heard it here first folks.
If you want a fun addition to your cookie box, these are for you! Keep a stash in the freezer, I promise you’ll want to be making these all month long!
Cookie Pro Tips
I tested this recipe enough times to learn exactly what makes or breaks these cookies. These tips are the difference between gorgeously soft cookies and flat, disappointing ones (or hockey pucks – we don’t want either of those).
- Measure your flour correctly.
Fluff the flour first, then spoon it into your measuring cup and level it off. Scooping directly from the bag packs in too much flour, which leads to dry, tough cookies. A kitchen scale is even better—use 225g total flour. - Use properly softened butter.
Creaming butter and sugar creates air, which gives these cookies lift and structure. Your butter should be room temperature—soft enough to leave an indent when pressed, but still cool and matte, not greasy or shiny. - Don’t overmix the dough.
You’ll fold in the cinnamon swirl while there are still a few streaks of flour left. This keeps the gluten from overdeveloping and ensures a soft, tender cookie. - Slightly underbake on purpose.
Pull the cookies when the edges look set but the centers still look puffed up and soft. They’ll finish cooking as they cool, giving you that gooey, chewy middle. - Chill the dough.
Chilling for at least 30 minutes (ideally 1–2 hours) lets the flour hydrate, deepens flavor, and prevents overspreading. Skip this and you’ll end up with thinner cookies. - For bakery-style round cookies.
Right after baking, use a cookie cutter or mason jar lid to gently scoot the cookies into perfect circles.
What Makes These Cookies Special
These cookies are inspired by snickerdoodles, but upgraded with cinnamon roll energy. Instead of mixing cinnamon sugar directly into the dough, the cinnamon swirl is frozen into a thin sheet, chopped, and folded in—this creates distinct ribbons and pockets of cinnamon sugar throughout the cookie.
They’re also rolled in cinnamon sugar before baking, which adds that unmistakable cinnamon roll aroma as they bake and gives the outside an extra layer of flavor.
After testing a version with a powdered sugar glaze, I ultimately skipped it. While it looked cute, it pushed the cookies into overly sweet territory, and required to wait until the cookies fully cooled to add. Without glaze, the balance of cinnamon, vanilla, butter, and salt really shines.
Speaking of salt and vanilla: don’t skip them. Think of them as seasoning, not optional extras. The vanilla rounds out the sweetness, and the salt keeps everything from tasting flat.
Cookie Storing Tips
If you want to make these ahead, store the unbaked cookie dough balls in an airtight container or ziplock in the fridge for up to 2 weeks, or in the freezer for up to 3 months.
Baked cookies will last for up to 1 week at room temperature in an airtight container.
Cinnamon Roll Cookies
- Total Time: 70 minutes
- Yield: 16 cookies
Description
Soft and chewy snickerdoodle-style cookies swirled with buttery brown sugar cinnamon filling and rolled in cinnamon sugar for a cookie that tastes like a classic cinnamon roll and a snickerdoodle had a baby.
Ingredients
For the Cinnamon Swirl:
- 5 tbsps unsalted butter, softened (71g)
- ½ cup lightly packed brown sugar (94g)
- 1 tbsp all purpose flour
- 1 tbsp cinnamon
For the Cinnamon Roll Cookies:
- ½ cup unsalted butter, room temperature (113g)
- ¾ cup packed brown sugar (150g)
- 2 tbsps granulated sugar (25g)
- 1 large egg, room temperature
- 1 large egg yolk, room temperature
- 1 tablespoon pure vanilla extract
- 1¾ cups all-purpose flour, scooped and leveled* (225 g)
- ¾ tsp salt
- ½ tsp baking soda
- ½ tsp baking powder
For the Cinnamon Sugar Coating:
- ¼ cup granulated sugar
- 1 tsp ground cinnamon
Instructions
For the Cinnamon Roll Cookies:
- Start by making the cinnamon swirl. Mix the softened butter, brown sugar, flour, and cinnamon in a small bowl until smooth. Line a small plate or baking sheet with parchment, spread the mixture on one half, then fold the paper over it. Press it flat into a thin layer—almost like making a quick cinnamon “bark.” Pop it in the freezer for 10 minutes (or fridge for 20) while you make the cookie dough.
- Now make your cookie dough. In a large bowl, add the butter, brown sugar, and white sugar, and beat on low with a hand or stand mixer until combined, then increase the speed to medium and beat until light and fluffy, about 2 minutes. Use a silicone spatula to scrape down the sides.
- Add the egg, egg yolk, and vanilla, and beat on medium high speed until lightened in color, about 1-2 minutes.
- In a separate bowl, whisk together the flour, salt, baking soda, and baking powder.
- Gently fold the dry ingredients into the wet until just a few streaks of flour remain. Remove the cinnamon swirl from the freezer or fridge and remove the parchment paper. Chop into small bite sized pieces and add to the cookie dough. Gently fold until combined. You want to have some cinnamon swirls and some chunks.
- Using a 2 tbsp cookie scoop, scoop the dough into balls and add to a parchment paper lined baking sheet. Cover the dough with plastic wrap and refrigerate at least 30 minutes, ideally 1 hour. This helps improve the flavor of the cookies and keeps them from spreading too much.
- Preheat the oven to 350°F.
- Make the cinnamon sugar coating. In a small bowl, mix together the sugar and cinnamon until combined.
- Line another baking sheet with parchment paper and roll the cookie dough into smooth balls and toss in the cinnamon sugar to coat. Place on a baking sheet 2-3” apart, baking in batches to not overcrowd the pan.
- Bake in a 350°F oven for 8–10 minutes, until the edges look set but the centers still appear soft. You want to pull these when they are slightly underbaked as they will continue cooking as they rest. While cookies are still warm, use the top of a mason jar or cup to round the cookies into a perfect circle.
- Let the cookies cool on the baking sheet for 5 minutes—they’ll be very soft—then transfer to a wire rack to cool for another 5–10 minutes.
- Store baked cookies in an airtight container at room temperature for up to 1 week, or freeze the unbaked dough balls for up to 3 months.
Notes
*Fluff the flour first, then spoon it into your measuring cup and level it off. Scooping directly from the bag packs in too much flour, which leads to dry, tough cookies. A kitchen scale is even better—use 225g total flour.
- Prep Time: 30
- Cook Time: 8-10
- Category: Dessert