These soft Cinnamon Roll Cookies are a cinnamon-lover’s dream come true! Take some cinnamon roll filling, swirl it into some Snickerdoodle dough, dunk it in more cinnamon-sugar, then die and go to heaven. This Cinnamon Cookie recipe is easy and so delicious! Originally published September 25, 2021.  

soft cinnamon roll cookies with cinnamon swirl on parchment paper.

You guys, have you been to the women’s clothing section at Target lately?

I don’t know WHAT is going on, but it’s like walking into the past. The DISTANT past. The past that none of us were a part of. The past where people wore petticoats and chopped their own wood.

soft cinnamon roll cookie with cinnamon swirls with a bite taken out of one.

What is this, pioneer chic?? The name of one of the dresses I saw actually has “Balloon Sleeve” in the title. It looks like it’s straight out of Little House on the Prairie! (Or do you remember Anne’s puffed sleeves from Anne of Green Gables?)

My girlfriends and I have a group text and every time one of us goes shopping, we send each other more evidence. It’s quite horrifying to think that if this trend keeps up, I will be wearing these ugly dresses in 3-5 years.

cinnamon roll cookies with cinnamon swirl on a baking sheet

At least that’s what happened with skinny jeans. Remember those? I resisted that trend for YEARS back in the early 2010s. I rocked those boot cut pants and slightly flared jeans much longer than I should have, because I was so resistant to the idea. These days? I LOVE my skinny jeans and am horrified that all these millennials are telling us they are out of style. (And now pioneer dresses are in? What is WITH YOU GUYS??)

hand picking up cinnamon snickerdoodle cookies

But if we don’t resist as a society, this is my fate. Balloon sleeved pastel pioneer dresses with tiny floral print. I am beholden to the whims of Target fashion. We must resist!! WHO’S WITH ME??

Cinnamon Roll Cookies = HEAVEN!

In other news, my tongue is completely numb and has been for hours. It’s because I’ve eaten literally nothing but Cinnamon Roll Cookies all day today.

soft cinnamon roll cookies stacked up with bites taken out

Does this happen to anyone else?? Or am I the only one with a mild cinnamon allergy. It’s never enough to stop me. We are not talking anaphylactic shock over here, just a weird numb feeling. I will eat Cinnamon Rolls, Snickerdoodles, and cinnamon toast all day long…and eventually just lose feeling in my tongue.

It’s all been worth it though. I bring you…the world’s most cinnamon-sugar-glorious cookie! (Can you tell I had a hard time picking a title, ha.)

cinnamon roll cookies recipe stacked on a baking sheet

This recipe all started when I went to create the perfect Snickerdoodle. I tried all kind of things to incorporate even MORE cinnamon flavor into the cookies (I’m a glutton for punishment, what can I say. Look at all this tongue numbing I’ve endured for you!)

Cinnamon Rolls are everyone’s favorite, so I whipped up some of the filling and swirled it into a Snickerdoodle to cookie-ify it. The result is FANTASTIC.

cinnamon snickerdoodles with cinnamon swirl with a bite taken out

I love them so much that I made a whole different post for them, even though they are very similar to these Perfectly Soft and Chewy Snickerdoodle Cookies that I just posted.

Because the truth is that the cinnamon roll filling changes the whole flavor profile of the cookie. They don’t taste like Snickerdoodles anymore, they taste like glorious cinnamon rolls.

They are super easy to make, you just need a few minutes to freeze the cinnamon roll filling. Let’s jump in!

cinnamon roll cookies on a pan layered together from overhead

Cinnamon Roll Cookie Recipe Ingredients

Basic pantry ingredients! Full recipe instructions are in the card below, as always.

  • salted butter, softened
  • brown sugar, packed
  • cinnamon
  • granulated sugar
  • large eggs
  • vanilla extract
  • all-purpose flour
  • baking soda
  • kosher salt
  • cream of tartar

Tips to make this Cinnamon Roll Cookie recipe

First we’re going to start by mixing up the cinnamon roll filling. Take some softened butter and beat it with cinnamon and brown sugar.

soft butter, cinnamon roll filling in a bowl with spatula

Then use a spoon to make little balls of filling, about the size of a marble. Line them up on a pan or a plate that will fit inside your freezer. It’s kind of like we’re making our own chocolate chips! Except they are cinnamon roll chips. YUM.

small marble size balls of cinnamon roll filling on a baking sheet

Once your dough is mixed together (see my Snickerdoodles recipe for more step-by-step photos on making the dough!), fold in the frozen cinnamon roll filling. Don’t use the mixer, it will beat them up too much. Use a wooden spoon or spatula to gently fold them in, trying to keep the cinnamon roll filling intact in little balls. We want those big swirly spots of cinnamon in our cookies.

snickerdoodle dough in a stand mixer bowl with cinnamon roll filling balls mixed in

After that, shape them using a cookie scoop or ice cream scoop. I like to make them about 2 inches across. When you scoop the dough, your cinnamon will swirl into the dough a bit, that’s okay.

cinnamon roll cookie dough being rolled in cinnamon sugar in a white bowl

Roll the balls of dough in cinnamon sugar, just like a Snickerdoodle.

raw dough balls lined up on a baking sheet, shot from overhead

If you don’t stop to eat some now, are you even human? Real talk. By the way, you can take these balls of dough and toss them right in the freezer to bake later. See recipe notes.

The Spoon Trick

Now it’s time to bake. Here they are just out of the oven.

cookies just out of the oven on a baking sheet

Oh no! Failure cookies! They have spread out too much and are running into each other and will collapse into pancake cookies with too-crispy-edges and no textured height in the middle! You should be shedding actual tears at this point.

cookies on a baking sheet being pushed into themselves with a spoon

But wait! A couple of spoons save the day. Just use your spoon when the cookie is still HOT, like within 30-60 seconds of removing it from the oven, and smoosh the cookies together a little bit. See my Snickerdoodles recipe for lots of details on this technique!

smooshing a cookie in on itself with fingers, to make the cookie chewy

Basically, we are smooshing to get more height and chewiness in our cookies (read: SOFT cookies), and to solve the problem of the spreading cinnamon filling. It only takes a minute to do and the results are pretty amazing! Almost every cookie that comes out of my kitchen these days gets spooned.

cinnamon roll cookies recipe on a baking sheet shot from overhead

That’s it! Only about 35 minutes from zero to hot, gorgeous Cinnamon Roll Cookies in your mouth! I know I say this every time, but I really do think these are my new favorite cookie. Am I crying wolf? Cinnamon is just the best, okay? (Even with the numb tongue. That’s how you know it’s true love guys.) One last thing, for all you cookie newbies:

cinnamon roll cookies with bite taken out on a pan with cinnamon sprinkle

What about a glaze??

What’s a cinnamon roll without a little glaze, right? Well when I shot this recipe, I was making it as a variation of these Snickerdoodles and originally was just going to throw this idea into that post, like here’s what they look like with a little cinnamon filling. But they tasted SO good, and SO much like cinnamon rolls, that I decided to create an entire other post and call them Cinnamon Roll Cookies. I completely forgot about a glaze and to be honest, don’t feel that they need it. I love letting that dark cinnamon swirl shine. BUT! If you want a glaze, use the one on this Cinnamon Roll Sugar Cookies recipe. For that recipe you roll out sugar cookie dough and roll it up with cinnamon filling, just like cinnamon rolls. Yes, I now have TWO Cinnamon Roll cookie recipes on my site. I told you, I love cinnamon 😉 No regrets!!

cinnamon roll cookies on parchment paper shot from overhead

Cinnamon Cookies FAQ

Can you freeze this Cinnamon Roll Cookie recipe?

Yes definitely! Just toss them in a ziplock bag and seal completely. Let them thaw at room temperature. They will keep for 3-4 weeks!

You can also 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!

What makes your cookie soft and chewy?

The secret to a soft and chewy cinnamon roll cookies is actually the cream of tartar. It acts as a leavening agent which makes the texture of the cookies so soft! Don’t skip it!

Why do my cookies get hard after they cool?

The cookies are naturally going to set up more as they cool off. That is precisely why we take them out while they are still slightly underdone! If you bake them too long, you’ll end up with crunchy cookies once they cool. 

I also recommend pulling the cookies off of the baking sheet pretty quickly after they’re done. Otherwise, they’ll continue to cook on the hot pan. I let them sit for 5 minutes so they don’t completely fall apart, then I transfer them to a wire cooling rack to cool completely.

More cookies to craze over!

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The BEST Cinnamon Cookie Recipe

4.80 from 125 votes
Prep: 25 mins
Cook: 11 mins
Total: 36 mins
Servings: 33 cookies
These soft Cinnamon Rolls Cookies are a cinnamon-lovers dream come true! Take some cinnamon roll filling, swirl it into some Snickerdoodle dough, dunk it in more cinnamon-sugar, then die and go to heaven. This recipe is easy and so delicious!

Ingredients

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
  • 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

Instructions

  • 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.
  • 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)
  • 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.
  • 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.
  • 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.
  • Add 3 and 1/2 cups flour but don't mix it in yet (make sure you spoon and level your flour).
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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:
  • 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.
  • 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!
  • 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!

Nutrition

Calories: 189kcal | Carbohydrates: 28g | Protein: 2g | Fat: 8g | Saturated Fat: 5g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 2g | Trans Fat: 1g | Cholesterol: 32mg | Sodium: 160mg | Potassium: 54mg | Fiber: 1g | Sugar: 17g | Vitamin A: 254IU | Vitamin C: 1mg | Calcium: 18mg | Iron: 1mg
Course: Dessert
Cuisine: American
Calories: 189
Keyword: 30 Minute Recipes, Cinnamon, Cookies, snickerdoodle
Did you make this? I’d love to see it!Mention @thefoodcharlatan or tag #thefoodcharlatan!

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Comments

  1. 5 stars
    When you said “a cinnamon lover’s dream come true” you were not kidding! I am a cinnamon lover for sure and these were amazing. The pockets of cinnamon sugar filling are intensely delicious. My son (who doesn’t love rich chocolate things) absolutely adored these. It’s nice for a non-chocolate cookie to pack such a punch! I will definitely be making these again.

  2. 5 stars
    Holy buckets are these cookies amazing! I just made them for the first time and sighed out loud after the first bite. Slightly more labor intensive then standard drop cookies but not complicated and 1000 times worth the extra effort! Thank you for sharing!

    1. It’s always a good sign when dreamy sighs are involved, right Ingrid? haha! So happy you loved them, thank you for commenting!

  3. 5 stars
    Holy WOW! These are some of the best cookies I have EVER had!!!! They are SO good! I sandwiched them with cannoli filling and they are a treasure! I’m making a second batch because I love them that much! Thanks for the recipe!

  4. These look amazing! Would you by chance have the grams conversion for the 3 1/2 cups of flour? I appreciate your recipes!

    1. Hi Heather! 3 1/2 cups of flour is about 440 grams. I always search Google for these types of conversions whenever I need them in a hurry! Enjoy baking :-)

      1. Hi Sarah,
        I put in 3 1/2 cups of all purpose flour in different converters as well as Google and it states 438 grams everywhere. How did you get to the conclusion of 507 grams? This is a big discrepancy for a baking recipe?

        1. Hi Mel! Thanks for catching my mistake; the first Google result was off by quite a lot! I’ve cross referenced it with other sources and you’re right, 3.5 cups of flour is about 438 grams. I’ve updated my comment.

  5. 5 stars
    Hey, delicious recipe! Snickerdoodles and cinnamon rolls are two of my most favorite carbs, so why not meld them together? I used another commenter’s method for the cinnamon filling; I spread it flattish and froze it then broke it into little chunks. My mistake was adding them to the dough before I double checked to make sure all the dry ingredients had been incorporated so they ended up getting mixed into the snicker dough more than I intended. Still turned out nice, with some variation in color as intended. I used a 1.5 Tbsp cookie scoop and they still spread until they touched, perhaps bc the filling was mixed in too much? Anyway the spoon technique worked fine on them and they split the difference between crispy and chewy. They are a bit greasy from all the butter but hey, I’m not complaining. 8.5/10, would scarf again

  6. 5 stars
    These turned out great. I tweaked the recipe a little by mixing the dry ingredients in another bowl before adding in 3 stages. I also made the cinnamon balls the day before and out them in the freezer. Pulled the cinnamon balls to the fridge when I started the dough. I did cut each ball in half when placing into the dough. I put the mixing bowl back into the fridge between each batch, and the cookies maintained a beautiful puffed appearance. I didn’t have enough for a full batch on the last go round, so I tried a wacky idea and made mini cookies. About 1/3 apiece. So cute! Much more work though. Yummy recipe, thank you!

    1. I’m so happy you loved it Brittany! Mini cookies sounds fun. Thanks for providing all these details, it’s always fun to hear other people’s processes. Thanks for chiming in!

  7. Before I try these, one question: when you bake cookies from frozen, does that change the texture in any way or solve the issue of needing to shape the cookies after they are baked? These look amazing and I think will adapt well to gluten-free for my Cookie Monster husband!

    1. Hi Marina! great question. It does not change the texture, in my opinion. I bake cookies from frozen all the time. Sometimes baking from frozen does make cookies stay puffier, but because these ones have the cinnamon swirl (which tends to ooze) you will probably need to use a spoon or shape them somehow after baking. Enjoy!!

  8. 5 stars
    These turned out absolutely amazing and satisfied the cinnamon roll craving I was having. To save time, I rolled out the filling between parchment to about 1/8 inch sheet, froze until firm, cut it into strips and then cut again to get squares or “chips”. Quick, easy and delicious, my new fave!

  9. 5 stars
    First of all, I want to thank you, Karen, because these cookies are seriously AMAZING!!! I brought them to a party and they were the talk of the night! Thank you for such a great recipe!

    Second, I want to share a tip. I love the result of the double-spoon-cookie-shaping technique but found it a bit difficult. I may have a method that’s a bit easier and faster. Take something circular a little larger than the cookie (e.g., water glass, circular cookie cutter, small bowl). Place it around the cookie and swirl the cookie around inside it. I found it a little less awkward than using the spoons and the results were more even for me. I hope this helps someone! The problem with this technique is it is a bit harder on a crowded cookie sheet. I ended up baking them six at a time to leave room to swirl.

    Finally, FWIW, I was considering making a glaze. After all, what’s a cinnamon roll without frosting? But I can report you really don’t need it. ;)

    1. Hey Kyle! So happy to hear you enjoyed these cookies! I have tried the circular method and am not a fan. I usually end up destroying my cookie in the process 😂 and I like to be a little more forceful with my spoon pushes :) But I know it works really well for some people! Thanks so much for sharing this tip!

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