Cinnamon Roll Cookies Recipe | Cookies and Cups

Cinnamon Roll Cookies are thick, soft, buttery cookies, swirled with cinnamon sugar and topped with sweet icing. All the flavors of a cinnamon roll in a EPIC cookie recipe!

Cinnamon Roll Cookies Are Going to Be Your New Favorite Cookie Recipe!

Oh friends, you are in for a real treat today, a real treat indeed. I have been thinking about the idea for these Cinnamon Roll Cookies for quite a while. And I will tell you there was some trial and error to get them how I imagined. Let me explain.

We LOVE Cinnamon Sugar desserts. From the Best Snickerdoodle Cookies ever to exist, to Cinnamon Roll Cake to Churro Bars and literally everything in between, I have so many cinnamon sweet treats here on my site. But these cookies, OH these cookies…they might be my best creation in a while. I know I say that a lot, but these are just truly epic cookies. You guys are going to LOVE them.

What Makes These Cinnamon Roll Cookies SO Great?

Like I’ve said, I have had the idea for this cookie recipe in my brain for a bit of time. And getting them exactly right took some trial and error. I knew I didn’t want a Cinnamon Roll Cookie that looked like mini cinnamon rolls. I’ve seen those all around the internet and they are so cute, but it wasn’t what I was going for. I didn’t want a fussy looking cookie, AND I wanted to make sure that my recipe made THICK, ultra-soft cookies with a slightly crisp edge, and melty, buttery centers, with ribbons of cinnamon sugar in every bite.

After 7 different batches, that were *almost* right, I nailed it on the 8th try. And then I tried them again 2 more times to makes sure. It’s been a cookie filled week, but I wouldn’t have it any other way.

These Cinnamon Roll Cookies were worth every.last.calorie.

Let’s Talk About How To Make Cinnamon Roll Cookies

There are a few easy tricks to make these cookies. They aren’t fussy or difficult, just a few instructions to ensure success!

Make the cinnamon sugar filling first (as per the instructions). The recipe calls for melted butter, so it’s easy to mix, but as it sits for a few minutes while you make your cookie dough, it thickens back up as the butter cools making it easier to spread than when the butter is completely melted.
Don’t worry about making things perfect. The beauty of these cookies is that they are rustic and non-fussy looking. When the cookie dough is made, spread it out into a large rectangle. I gave the measurements 10×15, but don’t get too hung up on this. This is a guideline, you don’t have to get out your tape measure. You just want the dough to be thin enough to roll up, and give you enough space to spread out the cinnamon sugar.
Also I just used my hands to press the dough into the rectangle shape. You CAN use a rolling pin, but it’s just as easy to press it into shape. It’s a pretty sticky dough, but you don’t want to add too much flour rolling it out, as that will change the texture of the cookie.
When you roll the dough up into a log, cut the pieces into 10 equal slices. You can absolutely make more than 10 cookies if you don’t want large cookies, just adjust your bake time down a few minutes.
Once you make the slices, pick up the slice and roll it into a ball! You want the ribbons of cinnamon sugar filling to swirl throughout the cookie in all directions. This also helps seal in the cinnamon sugar mixture, which contains a healthy amount of butter, and it can potentially leak out a little bit (which is fine) but rolling it into a ball helps seal it!
Place the dough balls into the freezer for 20 minutes before baking and while your oven is preheating. This helps keep the cookies on the thicker side. BUT while the first batch is baking place the remaining dough in the fridge. You don’t want the dough to be completely frozen, just cold.

Tips on How To Make Cinnamon Roll Cookies Pretty!

I feel like these are a stunner of a cookie…especially when you break one in half and see all those cinnamon sugar swirls! But I get asked a LOT how I make my cookies look so pretty, and here are a few tips for not only these cookies, but most cookie recipes!

Make sure all the cookies are the same size. Using a cookie scoop, a scale, or in this case, cutting the slices into equal portions ensures that the cookies are all the same size, which makes them bake evenly. If you have a small cookie and a larger cookie on the same baking sheet, clearly the smaller cookie will bake quicker than the larger.
As soon as the cookies come out of the oven grab a spatula and form them into the perfect circle. Sometimes cookies can spread in strange ways. This could be because of an oven that doesn’t heat evenly, ingredients that are different temperatures, dough that wasn’t mixed thoroughly, or in this case, the cinnamon sugar mixture is inside (and by design, isn’t completely uniform) which could cause it to spread more on one side than the other making non-symmetrical cookies. Using a spatula is a simple fix to form the cookie back into shape. This only works as soon as they come out of the oven when they are hot. As they cool they become less malleable.
The icing in this recipe is an easy way to make these cookies pretty. You can either dip the entire top into the icing to coat the surface, or drizzle it on top. I did it both ways, and it’s completely a personal preference. If you do dunk the entire top of the cookie into icing, you might want to make it a little thinner, adding an extra tablespoon of milk into the mixture. If you prefer to drizzle the icing in stripes, make it a little thicker. Don’t get too hung up on this step. If you on accident make it too thin, just add a little more powdered sugar. If it’s too thick, add more milk. You really can’t mess it up!

I have a STRONG suspicion that you guys are gonna go nuts for these cookies. Like they are pretty amazing. I love it when I have an idea that comes together in the way I imagine!

If you love Cinnamon Sugar Desserts I have tons more! Try these:

Description

These thick, buttery cookies have all the flavors of cinnamon rolls in cookie form!

Ingredients

Filling

1/4 cup butter, melted
1/3 cup dark brown sugar
1 1/2 teaspoons ground cinnamon

Cookie Dough

3/4 cup butter, room temperature
3/4 cup granulated sugar
1 large egg
2 teaspoons vanilla
3 tablespoons heavy cream
1 teaspoon baking powder
1/2 teaspoon kosher salt
2 1/4 cups all purpose flour

Icing

1 cup powdered sugar
2 tablespoons butter, melted
1–2 tablespoons milk

Instructions

For the filling, in a medium bowl combine the butter, brown sugar, and cinnamon. Set aside.
In the bowl of your stand mixer fitted with the paddle attachment combine the butter and the granulated sugar, mixing on medium speed for 2 minutes. Add the egg, vanilla, cream, baking powder, and salt. Mix for 1 minute, scraping the sides of the bowl as necessary. Turn the mixer to low and add in the flour, mixing until just combined.
On a lightly floured piece of wax or parchment paper, press the dough out into a 15×10 rectangle. This doesn’t have to be exact or neat.
Spread the filling mixture on top of the dough, leaving about an inch at the edges. Roll the dough up tightly from the long edge.
Cut the dough into 10 equal slices. Roll each slice into a ball and place on a lightly floured plate or baking sheet. Place into the freezer for 20 minutes.
Preheat the oven to 350°F. Line a large baking sheet with parchment paper.
Place 5 of the dough balls onto the prepared pan, leaving space for them to spread. Place the remaining dough in the refrigerator while the first batch bakes.
Bake for 15-17 minutes, until the edges are lightly golden.
Allow the cookies to cool on the pan for 5 minutes, and then transfer to a wire rack to continue cooling.
For the icing, in a medium bowl combine the powdered sugar, butter and 1 tablespoon milk. Whisk until no lumps remain. Add more milk if a thinner icing is desired.
Dip the tops of the cooled cookies into the icing, or drizzle on top. Allow the icing to set.