For the cinnamon roll and cookie lovers! These cookies feature a melt in your mouth sugar cookie dough swirled with a buttery cinnamon sugar filling and drizzled with a simple 2 ingredient icing. They're the perfect mix of soft & chewy and crisp & snappy and are so so warm and cozy!

iced cinnamon roll cookies on parchment lined board

These cookies are exactly what they sound like: they're all the goodness of a cinnamon roll in cookie form! Cinnamon rolls meet cookies. Cookies meet cinnamon rolls.

To make these cookies, we're using a sugar cookie inspired dough that's rolled out and filled with butter, sugar, and cinnamon. They're delicious as is or topped with a simple powdered sugar icing for some added sweetness.

The cookie dough bakes up into the perfect mix of crisp yet chewy. It's almost like a mix between chewy sugar cookies and melt in your mouth shortbread. Coupled with the warm and spicy cinnamon swirl, it's an elevated version of a classic vanilla cookie.

cinnamon roll cookie dough

The recipe starts with the cookie dough. It takes inspiration from sugar cookie dough and shortbread which creates a cookie that's soft but still buttery and melt in your mouth.

Making the dough is a lot like making a classic sugar cookie. It involves creaming together butter and sugar, adding in the remaining wet ingredients, and finishing off with the dry ingredients. Very low fuss, very easy to whip up, but now for the worst part: waiting!

The cookie dough needs some time in the fridge because it will be way too soft to roll out when it's first made. So once the dough is complete, it's divided in half and each half is shaped into a rough disk shape, wrapped with plastic wrap, and popped into the fridge.

Shaping the dough into 2 disks helps it chill faster and more evenly because there's more surface area exposed to the cold. This also makes it easier to roll out the dough later on because it's already been divided in two.

cinnamon roll cookie dough divided into 2 disks and wrapped in plastic wrap

rolling out the cookie dough

Once the dough is chilled and feels firm to the touch, it can be rolled, filled, and shaped. There's not much to consider when rolling out the dough, but here are a few tips that'll make for a much easier and smoother process:

Keep the second dough in the fridge when working on the first: This will ensure it stays nice and cool - making it easier to work with when the time comes.
For crack-free rolling: If you try to roll out a buttery dough when it's super cold, it will usually crack and tear. To prevent this, you have 2 options. 1) You can take the disk of dough out of the fridge about 10-15 minutes early. This will allow it to slightly soften to room temperature so the butter isn't too hard and the dough rolls more smoothly. Just be careful not to let it sit for too long or it'll be too soft. Or 2) you can lightly knead the dough with your hands to (again) slightly warm the butter to make it more malleable.
Roll on a floured surface: The cold dough will be significantly less sticky than when it was first whipped up, but it can still stick to your work surface and rolling pin. So make sure to sprinkle some flour as needed - but use it sparingly. Too much flour will dry out the dough.
Keep the dough moving: As you roll, regularly lift and slide the dough around to make sure the bottom isn't sticking.
And when in doubt... If the dough starts softening up while you're working on it, pop it back into the fridge to allow it to cool back down before continuing. The dough will soften slightly as you work on it but it shouldn't be excessive and it should still be easy to work with.

filled, rolled, and sliced cinnamon roll cookie dough on wooden cutting board

sliced cinnamon roll cookies arranged on parchment lined baking sheet before baking

shaping cinnamon roll cookies

Once the dough is rolled out, it can then be brushed with the melted butter and topped with cinnamon sugar. When filling the dough, make sure to leave a little bit of the dough on one of the long sides without any filling on it. You can see what I mean in the photos above - the right side of the dough has a little sliver without any butter or sugar.

This little border will allow you to stick the seam to the rest of the dough which will keep the cookies from unraveling in the oven. Lightly wet the exposed dough with water (to help the seam stick and seal up) then roll the dough up tightly (starting from the long end that has filling).

The dough will have softened quite a bit at this point so the log needs to be wrapped up and chilled again until it feels firm to the touch. This helps prevent overspreading and will allow you to slice the cookies easily without squishing them.

While the log chills, you can roll and shape the other half of the dough. Once the logs have chilled, all that's left is to slice and bake the cookies. You can serve the cookies plain or whisk together powdered sugar and milk for a simple icing to drizzle on top.

baked cinnamon roll cookies on wire rack

more tips

Measure flour correctly: No brainer, right? But you'd be surprised how easy it is to accidentally mismeasure flour and it can completely alter the texture of the cookies. Whenever possible, a food scale is the best way to measure flour because weight will always be the more accurate route. But if you are using cups, never scoop the measuring cup directly into the bag of flour. This will cause the flour to pack into the cup and results in more weight. Use a spoon to lightly scoop the flour into your cup then use a flat utensil to level off any excess.
Use room temperature ingredients: Room temperature ingredients are simply easier to work with and will combine much better. Using cold ingredients runs the risk of leaving behind clumps of undissolved ingredients which can cause the cookies to under / over spread, bake up greasy, bake up flat, and more.
Chilling the dough: It's an important step to make the dough easier to work with and to ensure the cookies spread just the right amount. So don't try to rush this by placing the dough into the freezer - it won't chill evenly and the flour will not get a chance to hydrate and soak up the additional moisture in the dough.
Storing the cookies: Allow the cookies to cool completely to room temperature then keep any leftovers tightly covered with plastic wrap or in an airtight container. These will keep for up to 1 week at room temperature.

iced cinnamon roll cookies stacked on serving board with one cookie split in half

check out these other cinnamon roll inspired recipes!

• Cinnamon Roll Cheesecake
• Cinnamon Roll Gooey Butter Cake
• Mini No Bake Cinnamon Roll Cheesecakes
• Mini Pie Crust Cinnamon Rolls
• Small Batch Cinnamon Rolls

Lastly, if you made this or any of my recipes, be sure to leave a comment and review below! I love hearing your thoughts! Also tag me on Instagram @eatsdelightfulblog so I can see what you're making.

Cinnamon Roll Cookies

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Author: Mimi
Total Time: 50 minutes + 3 hours chill
Yield: 24 cookies

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Description

Ingredients

For the cookie dough:

3 cups (390g) all-purpose flour + more for rolling
1 teaspoon baking powder
¼ teaspoon salt
1 cup (225g) unsalted butter, softened to room temperature
¾ cup (150g) granulated sugar
2 large eggs, at room temperature
2 teaspoons pure vanilla extract

For the cinnamon filling:

½ cup (100g) granulated sugar
2 teaspoons ground cinnamon
¼ cup (60g) unsalted butter, melted and cooled

For the icing (optional):

½ cup (65g) powdered sugar
½ tablespoon milk or water

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Instructions

Cookie Dough:

In a medium bowl, whisk together flour, baking powder, and salt to combine. Set aside.
In a large bowl, combine butter and sugar. Using an electric mixer fitted with the paddle attachment, cream together until light and fluffy (about 1-2 minutes on medium speed).
Whisk the eggs into the butter mixture, one at a time, followed by the vanilla.
Add the dry ingredients and mix everything together until you have a soft, streak free cookie dough. It will be quite sticky at this point.
Divide the dough in half and place each one on a sheet of plastic wrap. Use the plastic wrap to roughly shape each half of dough into a rough disk shape and wrap tightly.
Place the 2 cookie dough disks into the fridge to chill for about 1 hour or until firmed up.

Cinnamon Filling:

In a medium bowl, whisk together sugar and cinnamon. Set aside.
Take one of the chilled cookie dough disks out of the fridge. Unwrap and place onto a lightly floured work surface.
To make it easier to roll the dough out with minimal cracking, let it sit at room temperature for 10-15 minutes to soften slightly or you can lightly knead the dough with your hands to warm it up slightly. This will make it more malleable.
Roll the dough out, lightly dusting with flour as needed to keep it from sticking, until it's a rough rectangle shape measuring about 7x10 inches large and about ¼ of an inch thick. You can use your hands to push in the edges of the dough to even out the shape but it doesn't have to be perfect.
Brush half of the melted butter over the surface of the dough. Along one of the long sides, leave a small ¼" strip of the dough clear of any butter - this will be where the seam is once the dough is rolled up, so leaving it clear will allow the seam to stick more easily. (See above post for visual)
Sprinkle half of the cinnamon sugar evenly over the butter.
Lightly wet the exposed end of the dough with water (to help the seam stick). Working on the opposite long side of the dough (the side with filling), roll the cookie dough up into a log. The log should end where that clear strip of dough is.
Pinch the seam to seal then wrap the log of dough with plastic wrap. Repeat the process with the second dough.
Chill both logs in the fridge for at least 2 hours or up to overnight to allow them to firm up.
Line 2 large baking sheets with parchment paper and set aside.
Unwrap the chilled log of dough and place onto a cutting board. Cut off the ends then slice the dough into ½" thick cookies. You should get about 12 cookies out of each log - for a total of 24.
Arrange the cookies on your parchment lined baking sheets leaving about 2 inches of space between each cookie.
Place the cookies into the fridge to chill while you preheat the oven.
Preheat your oven to 350°F. Bake the cookies, one baking sheet at a time, in the center of your preheated oven for 15-20 minutes or until golden brown around the edges.
Cool the baked cookies for about 5 minutes on the baking sheet then transfer onto a wire rack and set aside to cool completely before icing.

Icing (Optional):

In a medium bowl, combine powdered sugar and ½ tablespoon of milk or water. Whisk together until you have a smooth icing. If the icing is too thick, whisk in a splash more milk / water.
Pipe or drizzle the icing over the cooled cookies and serve!

Equipment

KitchenAid Stand Mixer

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2 Baking Sheets