Cinnamon Roll Cookies with Soft and Chewy Snickerdoodle Swirls

The BEST Cinnamon Roll Cookies

Okay, you guys. I need to tell you about the cookies that made me forget there was laundry in the dryer for two hours. These Cinnamon Roll Cookies are soft, chewy, and they taste like the gooey middle of a cinnamon roll, which is the only part of a cinnamon roll that anybody actually fights over.

Here is how they work. You swirl a real cinnamon roll filling into a Snickerdoodle dough, then you dunk the whole dough ball in cinnamon sugar before it goes into the oven. That is it.

Two of my favorite cookies bumped into each other and somehow came out better than either one alone. I first published this recipe on September 25, 2021, and it has been on repeat in my kitchen ever since.

They are easy. Real talk, if you can cream butter and scoop dough, you can make these. The only part that needs patience is the filling, and even that is just a short trip to the freezer.

Now a quick tangent, because I know why you are really here. I ran into Target for parchment paper and one birthday card.

I walked out with a cardigan, a candle that smells like a library, and a pair of jeans that the internet swore were the perfect fit. The jeans were not the perfect fit. The cardigan, however, is now part of my personality.

I wore it while testing these cookies three times in one week, so in my head the two are permanently linked. If you spot me in a mustard cardigan with cinnamon sugar on the sleeve, mind your business.

Anyway. Cookies.

Cinnamon Roll Cookies = HEAVEN!

So I ate nothing but these cookies all day, my tongue went completely numb, and I have zero regrets.

Here is the thing about me. I have a mild cinnamon sensitivity. Too much of it and my tongue goes a little numb, like I licked a battery, except pleasant. Does that stop me? It does not. I am not giving up cinnamon rolls, snickerdoodles, or cinnamon toast over a tingling tongue. I just eat them and accept my fate.

These cookies started as an accident, honestly. I was chasing the perfect Snickerdoodle, one with even more cinnamon flavor than my usual recipe. Somewhere along the way I decided to swirl actual cinnamon roll filling into the dough, and that changed everything.

The filling does not just add cinnamon. It changes the whole flavor profile. These stopped tasting like snickerdoodles and started tasting like cinnamon rolls wearing a cookie costume.

If you have made my Perfectly Soft and Chewy Snickerdoodle Cookies before, you already know this dough. Same soft, chewy base. The filling is what sends it somewhere new.

They are easy to make too. The one part that needs a few minutes is the filling, because it has to freeze into little balls before you fold it into the dough. That is your only waiting period. Set a timer, pour a coffee, and scroll your phone for 20 minutes like a normal person.

Cinnamon Roll Cookie Recipe Ingredients

Nothing fancy here, you guys. This is a basic pantry list with one small hero ingredient at the end. Full amounts and the printable card live below the post, but here is the whole lineup.

A quick note on the cream of tartar. It is the secret to a soft and chewy cookie, because it works as a leavening agent alongside the baking soda. Please do not skip it. Also, spoon and level your flour. Scooping straight from the bag packs in extra flour, and extra flour means dry, sad cookies.

For the record, the recipe card lists about 189 calories per cookie, with 28 grams of carbohydrates, 8 grams of fat, 2 grams of protein, and 17 grams of sugar. Cookies with a nutrition label are basically salad, and that is the rule I live by.

How to make Cinnamon Cookies

Start with the filling, because it needs time in the freezer while you work on everything else.

1. Make the filling. In a large bowl or stand mixer, beat 6 tablespoons softened butter until creamy and smooth. Add 3/4 cup packed brown sugar and 1 and 1/2 tablespoons cinnamon. Beat well, scraping the sides, until completely smooth.
2. Freeze it into little balls. Line a baking sheet or a platter with parchment paper or a silicone mat, and clear some freezer space. Spoon the filling into small balls about the size of a marble and line them up on the pan. You will have quite a few. Freeze for 20 minutes until hardened. If you only have room in the fridge, plan on 1 to 2 hours.
3. Preheat. Heat the oven to 350 degrees F and line a couple more baking sheets with parchment paper or a silicone mat.
4. Make the dough. In the same bowl, no need to wash it, beat 1 cup softened butter for a couple of minutes until smooth, scraping the sides and bottom.
5. Add the sugar. Beat in 1 and 2/3 cups granulated sugar for 2 minutes. It should look light and fluffy with no chunks at all.
6. Add the eggs and vanilla. Beat in 2 eggs and 2 teaspoons vanilla until smooth and homogenous.
7. Add the dry ingredients the smart way. Add 3 and 1/2 cups flour but do not mix yet. Stir 1 teaspoon baking soda, 3/4 teaspoon kosher salt, and 1 and 1/2 teaspoons cream of tartar into the flour with a small spoon. Then gently beat the flour mixture into the butter mixture. Stop while you still see flour streaks, then beat just a few more seconds until they are gone. Overmixing means tough cookies.
8. Fold in the frozen filling. Use a wooden spoon or a spatula, not a mixer. You want those little frozen balls to stay mostly intact so they melt into big swirly cinnamon spots in the oven.
9. Scoop. Use a large cookie scoop or a spoon to shape dough balls about 2 inches across. The cinnamon will swirl into the dough a bit as you scoop, and that is exactly what you want.
10. Roll in cinnamon sugar. Stir together 1/3 cup granulated sugar and 1 and 1/2 tablespoons cinnamon, then roll each dough ball in it to coat.
11. Space them out. Place the balls on the prepared sheets about 2 inches apart. I can fit 12 on an 11 by 17 inch pan, but they do run into each other, so 8 per pan is the safe play.
12. Bake. Bake at 350 degrees F for 11 to 12 minutes, then head straight to the spoon trick below.

You can also freeze the shaped dough balls right away and bake them later. More on that in the storage section.

The spoon trick for Cinnamon Roll Cookies

Here is the part where I tell you the truth about these cookies. They spread. They run into each other. Left alone, they can collapse into flat, pancake looking cookies with crispy edges and no height in the middle. I told you the cinnamon filling was dramatic.

The fix takes about a minute, and it is called the spoon trick.

Immediately after you pull the cookies out of the oven, seriously, within 30 to 60 seconds before the edges crisp up, grab a couple of spoons and push the edges of each cookie toward its center.

Shape them back into the circles they were meant to be. Scrape up all that oozing cinnamon sugar goodness and pack it into the edge of the cookie, pushing the cookie in on itself.

This makes every cookie thicker and chewier, and it solves the whole spreading cinnamon filling problem in one move.

Now, how do you know when to pull them out? These cookies are not going to look done, because the cinnamon filling stays shiny. Look at the edges that do not have filling pooling out the side. They should be firm but not golden. The white part on top should be matte, at least around the outer edges.

Let them set up on the pan for at least 5 minutes, then move them to a wire rack. From start to hot and ready, you are looking at about 36 minutes. Most of that is just the filling chilling while you do everything else.

If you only remember one thing from this post, make it this: the spoons come out within 30 to 60 seconds of the oven door opening. Wait any longer and the edges set, and then you are just pushing around a crispy cookie.

Do I glaze this Cinnamon Roll Cookies Recipe?

Fair question, and I have a strong opinion.

These started life as a variation on my Snickerdoodles. I planned to tuck them into that post as a little bonus. Then I tasted one and realized they tasted so much like cinnamon rolls that they deserved their own post, so I named them Cinnamon Roll Cookies and gave them a home.

Somewhere in all that excitement, I forgot about a glaze. And honestly? I do not think these cookies need one. I like letting that dark cinnamon swirl do the talking. A glaze would cover up the prettiest part.

That said, if you are a glaze person, I get it. Use the glaze from my Cinnamon Roll Sugar Cookies recipe. That one rolls out sugar cookie dough and rolls it up with cinnamon filling, just like actual cinnamon rolls. Yes, there are now two Cinnamon Roll cookie recipes on this site. I have no regrets and neither should you.

How to store Cinnamon Cookies

Keep these on the counter in a covered container. Real talk, they will not last long, and not because they go stale. They last because somebody in your house keeps walking past the container. In my experience that somebody is me.

If you somehow still have cookies after 2 to 3 days, freeze them in a ziplock bag. They keep for about a month. They are good straight from the freezer, though I like to warm one for a few seconds in the microwave, because that brings back the fresh from the oven feeling.

Can you freeze this Cinnamon Roll Cookie recipe?

Yes, in two ways.

Baked cookies go into a well sealed ziplock bag and thaw at room temperature. They keep for 3 to 4 weeks. The dough freezes beautifully too. Shape it into balls, roll each one in cinnamon sugar, and store them in a ziplock bag, where they keep for up to 3 months.

Here is the important part. Do not thaw the dough before baking. Bake straight from frozen and add a couple of minutes to the bake time. That is it. Warm cookies on a random Tuesday with almost no effort.

More cookies to craze over!

If these Cinnamon Roll Cookies wrecked your self control, welcome to the club. Here are the other cookies I keep in rotation, and yes, I have tested every single one on people who swore they were not hungry.

• Perfectly Soft and Chewy Snickerdoodles. The base of today’s cookie, and the reason this whole thing exists.
• Cinnamon Roll Sugar Cookies. Sugar cookie dough rolled up with cinnamon filling, just like a cinnamon roll.
• The Best Cinnamon Rolls. For the days when you want the full project.
• Mexican Hot Chocolate Cookies. Basically chocolate snickerdoodles with a little kick.
• Easy Old Fashioned Sugar Cookies. Crisp, classic, and no glaze required.
• Texas Cowboy Cookies. Big, loaded, and built for a crowd.
• Britta’s White Chocolate Chip Cookies. A hint of cinnamon hides in there, which is very on brand for me.
• Soft and Chewy Molasses Cookies. I make these by the dozen every Christmas.
• The Softest Peanut Butter Cookies. Heavy on the peanut butter, exactly as it should be.
• Levain Bakery Chocolate Chip Cookies from Oh Sweet Basil, thick and bakery style.
• Easy Sugar Cookies from BellyFull, for when you need something simple and quick.
• Shortbread Cookies from Love and Lemons, buttery with just a few ingredients.

Pick one, or bake them all and blame me later.

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The BEST Cinnamon Cookie Recipe

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The BEST Cinnamon Roll Cookies Okay, you guys. I need to tell you about the cookies that made me forget there was laundry in the dryer for two hours.

• Total Time: 36 min
• Yield: 33 cookies 1x

Ingredients

Scale 1x2x3x

For the filling
6 tablespoons salted butter, softened
3/4 cup brown sugar, packed
1 & 1/2 tablespoons cinnamon

For the dough
1 cup salted butter, 2 sticks, softened
1 and 2/3 cup granulated sugar
2 large eggs
2 teaspoons vanilla extract
3 and 1/2 cups all-purpose flour, spooned and leveled
1 teaspoon baking soda
3/4 teaspoon kosher salt
1 and 1/2 teaspoons cream of tartar

For rolling
1/3 cup granulated sugar
1 and 1/2 tablespoons cinnamon

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Instructions

1-Make the filling first: Make the filling first. In a large bowl or stand mixer, add 6 tablespoons softened butter. Beat well until it is creamy and smooth. Add 3/4 cup packed brown sugar and 1 and 1/2 tablespoons cinnamon. Beat well, scraping sides down, until completely smooth. Line a baking sheet or large platter with parchment paper or a silicone mat. Clear out space in your freezer, if possible. Use a spoon to create small balls of filling, about the size of a marble. Line them up on the prepared pan, you should have quite a few (see photos). Place in the freezer if you can fit it in. Freeze for 20 minutes until hardened. If you only have room in the fridge, you will have to wait about an hour or two until they are firm.
2-Preheat the oven to 350 degrees and: Preheat the oven to 350 degrees and prepare a couple more baking sheets with parchment paper, or line with a silicone mat. (You can use the pan in the freezer to bake later, too)
3-Make the dough: Make the dough. In the same large bowl or stand mixer (no need to wash it), beat 1 cup butter for a couple minutes until smooth, scraping the sides and bottom a few times in between.
4-Add 1 and 2/3 cup white sugar: Add 1 and 2/3 cup white sugar. Beat for 2 minutes, taking the time to scrape the bottom and sides of the bowl in between. Your butter and sugar should be light and fluffy with no chunks at all.
5-Add 2 eggs and 2 teaspoons vanilla: Add 2 eggs and 2 teaspoons vanilla. Beat well, scraping the sides and bottom of the bowl. Make sure you beat it long enough that it becomes smooth and homogenous.
6-Add 3 and 1/2 cups flour but: Add 3 and 1/2 cups flour but don’t mix it in yet (make sure you spoon and level your flour).
7-Use a small spoon (I use my: Use a small spoon (I use my teaspoon) to stir in 1 teaspoon baking soda, 3/4 teaspoon kosher salt, and 1 and 1/2 teaspoons cream of tartar into the flour. Gently beat the flour mixture into the butter mixture. Don’t overdo it. There should still be flour streaks when you stop your mixer. Use a spatula to scrape down the edges of the bowl.
8-Continue beating just a few more seconds: Continue beating just a few more seconds until all the flour streaks are gone. Do not over mix! You want to make sure all the ingredients are combined, but once that is done, stop mixing. Over mixing dough = tough cookies.
9-Mix in: Mix in. Once your small balls of cinnamon filling are frozen and firm, you can add them to the dough. Do not use a stand mixer or hand mixer. Instead, fold them in with a wooden spoon or a spatula.
10-Use a large cookie scoop or a: Use a large cookie scoop or a spoon to shape the dough. You want dough balls that are about 2 inches across. I used this cookie scoop. and overfilled it slightly for each scoop. See photos.
11-Roll the cookies: Roll the cookies. In a small or medium bowl, add 1/3 cup sugar and 1 and 1/2 tablespoons cinnamon. Stir together. Roll the shaped cookies in the cinnamon-sugar to coat.
12-Place cookie dough balls on the prepared: Place cookie dough balls on the prepared baking sheet with about 2 inches in between them. I can fit 12 cookies on an 11×17 baking sheet. But as you can see from the photos, they kind of run into each other. You can fix this with the spooning technique, but if you want to play it safe add 8 cookies to a pan.
13-Bake the cookies at 350 for about: Bake the cookies at 350 for about 11-12 minutes. These cookies are not going to look done when you take them out of the oven because the cinnamon filling will stay shiny. The edges of the cookies that DON’T have cinnamon filling pooling out the side should be firm but not golden. The top (white) part of the cookies should be matte (not shiny), at least on the outer edges. The cinnamon filling will be shiny and may or may not be spreading quite a bit. You might think these cookies are going to flatten out and crisp up and fail, but never fear, we have a plan:
14-Shape the cookies: Shape the cookies. Immediately after taking the cookies out of the oven (like seriously, within 30-60 seconds before the edges crisp), use a couple spoons to push the edges of the cookies toward their centers. Shape them back into the circle that they were meant to be. See photos! Scrape up all that oozing cinnamon sugar goodness and pack it into the edge of the cookies, pushing the cookies in on themselves. This makes the cookies thicker, chewier, and solves the problem of the cinnamon filling spreading everywhere.
15-Let the cookies set up on the: Let the cookies set up on the pan for at least 5 minutes. Remove the cookies to a wire rack. Then eat one as fast as you can with a glass of milk! Cinnamon roll blissss!! Don’t forget to try out my regular Snickerdoodle recipe sometime, it’s almost the same recipe but instead of the cinnamon filling, it gets double dipped in cinnamon-sugar before and after baking. They are perfectly soft and chewy!
16-Freezer instructions: Freezer instructions: You can freeze this dough and bake later! I like to shape the dough into balls, roll them in cinnamon sugar, and store them in a ziplock bag. They will keep in the freezer for up to 3 months. I never thaw cookie dough before baking. Just bake straight from frozen and add a couple minutes to the bake time. Voila!

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• Prep Time: 25 min
• Cook Time: 11 min
• Method: bake

Nutrition

• Calories: 189
• Sugar: 17g
• Fat: 8g
• Saturated Fat: 5g
• Carbohydrates: 28g
• Fiber: 1g
• Protein: 2g
• Cholesterol: 32mg