Soft Cinnamon Roll Cookies with Brown Sugar Swirl
These cookies take everything you love about a cinnamon roll and tuck it into a tender, buttery swirl. A soft vanilla dough gets rolled up with a cinnamon sugar filling, sliced into rounds, and baked until the edges turn crisp and the centers stay soft. A quick vanilla glaze drizzled over the top makes them feel a little extra, even on a Tuesday night.
What Makes Them Taste Like a Cinnamon Roll
You get the same ribbon of cinnamon filling you would expect in a pan of rolls, except it runs through a cookie instead of yeast dough. The butter in the filling melts into the cookie as it bakes, leaving little caramelized pockets that crackle around the edges. Every bite lands somewhere between sugar cookie and cinnamon bun, with exactly the amount of icing you want.
It is a simple dough you can make in one bowl with a hand mixer, and the filling comes together in 30 seconds. I keep this recipe in my back pocket for bake sales and snow days because the dough freezes well and the cookies look way fancier than the effort they take.
Ingredients
- 1 cup unsalted butter, softened: take it out of the fridge about an hour before you start
- 1 cup granulated sugar: keeps the cookie crisp on the outside
- 1 large egg: cold is fine, it comes to room temp in the mixer
- 2 tsp vanilla extract: use the real stuff if you have it
- 2½ cups all-purpose flour: spooned and leveled, not scooped
- ½ tsp baking powder: just enough lift
- ½ tsp salt: fine sea salt or table salt
- 3 tbsp unsalted butter, melted and cooled slightly: for the filling
- ⅓ cup packed light brown sugar: for the cinnamon swirl
- 1 tbsp ground cinnamon
- 1 cup confectioners’ sugar: for the glaze
- 2 to 3 tbsp milk or cream: to thin the glaze
- ¼ tsp vanilla extract: for the glaze
Variations / Substitutions
- Dairy-free: swap the butter for a good vegan butter stick and use a plant-based milk for the glaze, the texture will be a little softer but still swirled.
- Brown butter filling: use browned butter for the melted butter in the filling for a nuttier, deeper flavor.
- Extra spice: add ¼ tsp nutmeg or cardamom to the cinnamon sugar for a warm spice cookie.
- No glaze: the cookies are still sweet without the icing, just sprinkle with a pinch of flaky salt when they come out of the oven.
If you like this swirled idea, try our Snickerdoodle Bread for another cinnamon sugar fix.
How to Make Soft Cinnamon Roll Cookies
Step 1: Cream the Butter and Sugar
In a large bowl, beat the 1 cup softened butter and 1 cup granulated sugar with a hand mixer on medium speed for about 2 minutes, until the mixture looks fluffy and pale. Scrape down the sides of the bowl, then beat in the egg and 2 tsp vanilla extract until they disappear into the dough.
Whisk together the 2½ cups flour, ½ tsp baking powder, and ½ tsp salt in a separate small bowl. With the mixer on low, add the flour mixture in two additions, beating just until you stop seeing dry streaks. The dough will be soft and thick like a stiff buttercream; stop mixing as soon as it comes together so the cookies stay tender.
Step 2: Whisk the Cinnamon Filling
In a small bowl, stir the 3 tbsp melted butter, ⅓ cup brown sugar, and 1 tbsp cinnamon together with a fork until it forms a wet, grainy paste. It should look like damp sand and be spreadable but not runny. If it feels too thick to spread, add half a teaspoon of melted butter to loosen it just a touch.
Step 3: Roll the Dough with Filling
Turn the dough out onto a piece of parchment paper and pat it into a rough rectangle about 9 by 12 inches. Spoon the cinnamon mixture over the surface and use an offset spatula or the back of a spoon to spread it into an even layer, leaving a ½-inch border around every edge. Starting from one long side, use the parchment to help you roll the dough into a tight log, peeling the paper back as you go.
Roll it slowly and evenly, pressing gently so the filling stays tucked inside and does not ooze out the ends. When you reach the other side, pinch the seam closed and roll the log back and forth on the counter once or twice to seal it.
Step 4: Slice the Dough Log
Wrap the log in the same parchment, twist the ends shut, and refrigerate it for at least 1 hour until it is firm enough to cut cleanly. Chilling solidifies the butter in the dough and keeps the cookies from spreading into puddles in the oven. When you are ready to bake, preheat the oven to 350°F (175°C) and line two baking sheets with parchment.
Unwrap the log and slice it into rounds just under ½ inch thick, you should get about 24 cookies. Use a thin, sharp serrated knife and a light sawing motion so the spiral stays crisp instead of squishing flat.
Step 5: Bake and Drizzle with Glaze
Arrange the slices on the prepared sheets about 2 inches apart and bake one sheet at a time on the middle rack for 10 to 12 minutes, until the edges are set and lightly golden. The centers will look a little underdone but will firm up as the cookies cool. Let them rest on the sheet for 5 minutes, then transfer them to a wire rack to finish cooling completely.
While they cool, whisk the 1 cup confectioners’ sugar, 2 tbsp of the milk, and ¼ tsp vanilla extract in a small bowl until smooth. Add the remaining milk a little at a time if you like a thinner drizzle. Spoon the glaze over the cooled cookies in zigzag lines and let it set for about 10 minutes before serving.
A Few Notes Before You Start
- The dough needs that full hour in the fridge. If you try to slice it warm the spiral will flatten and the filling will smear.
- For the cleanest cut, roll the log back and forth a few times after shaping to round it out, then freeze it for 10 minutes before slicing if you have the time.
- Keep a close eye on the oven at the 10-minute mark. These cookies go from soft and pale to overbaked quickly, and a crisp edge is all you want.
Bake times by slice thickness:
| Slice Thickness | Bake Time at 350°F |
|---|---|
| ¼ inch | 8 to 10 mins |
| just under ½ inch (standard) | 10 to 12 mins |
| ½ inch | 12 to 14 mins |
Storing Leftovers
- Refrigerate: keep the baked cookies in an airtight container at room temp for up to 4 days, or in the fridge for up to a week. The glaze stays slightly soft.
- Freeze the dough log: wrap the unsliced log tightly and freeze for up to 2 months. Defrost in the fridge overnight, then slice and bake as written. You can also freeze the unglazed baked cookies in a single layer until solid, then stack them in a freezer bag for up to a month.
Frequently Asked Questions
Can I use premade sugar cookie dough?
You can. Roll a 16-ounce log of prepared sugar cookie dough into a rectangle, spread the filling, and roll it up. The texture will be a little softer and the bake time will stay about the same.
Do I have to add the glaze?
No, the cookies are sweet enough on their own. A light dusting of confectioners’ sugar before serving looks pretty and skips the extra step.
Why did my cookies spread too much?
The dough was likely too warm. Make sure the log chills for the full hour and that your baking sheets are cool between batches. A hot sheet starts melting the butter as soon as the dough hits it.
Can I double the recipe?
Yes, split the dough in half and make two logs. Keep the second log wrapped in the fridge while you slice and bake the first one so nothing gets too soft.
Cinnamon Roll Cookies Recipe
Ingredients
Method
- Cream 1 cup butter and 1 cup granulated sugar until fluffy, then beat in the egg and 2 tsp vanilla. Stir in the flour, baking powder, and salt to form a soft dough.
- Mix 3 tbsp melted butter, brown sugar, and cinnamon into a spreadable paste.
- Pat the dough into a 9×12-inch rectangle on parchment, spread the filling evenly, and roll tightly into a log from the long side.
- Wrap and chill the log for at least 1 hour. Preheat oven to 350°F. Slice into just under ½-inch rounds and place on lined baking sheets.
- Bake 10 to 12 minutes until edges are golden. Cool completely, then whisk confectioners’ sugar, milk, and ¼ tsp vanilla and drizzle over cookies.
