These soft and chewy sugar cookies are swirled with brown sugar cinnamon filling and topped with heavenly cream cheese frosting! A cinnamon roll in cookie form!
If there’s any breakfast pastry that I absolutely CANNOT get enough of, it HAS to be cinnamon rolls. As a cinnamon-sugar-a-holic, I’m obsessed with that combination of fluffy yeasty dough, maple-y brown sugar, and warm cinnamon.
Seeing as I’ve already made my fair share of cinnamon rolls on this blog, I decided to try something a little different…so why not incorporate the heavenly flavors of a cinnamon roll into a soft and chewy cookie?
These Cinnamon Roll Cookies taste exactly like a cinnamon roll, but in sugar cookie form! Each and every delectable cookie contains that same brown sugar cinnamon swirl we all swoon over as well as that dreamy cream cheese frosting we just can’t get enough of.
Although you can never replace the deliciously doughy experience of a good ol’ cinnamon roll, I must say that I ADORE the soft and buttery sugar cookie dough in these cookies. It’s perfectly chewy around the edges and supremely soft in the center. Not to toot my big fat horn or anything, but these cookies are an 11 out of 10 in my book!
When it comes to making these cookies, they really aren’t that different from cinnamon rolls. In fact, the only difference is that the dough rise normally called for in cinnamon rolls is replaced with dough chilling.
The first thing you’ll do is make up the cookie dough. Start by combining the dry ingredients–all-purpose flour, baking soda, and salt–in a bowl. Then, in a separate bowl (or stand mixer), beat some butter and sugar together until nice and creamy. Add the eggs, one at a time, followed by a little vanilla and some instant vanilla pudding mix. Not only does the pudding mix keep these cookies soft and THICC, but it also adds that delicious vanilla sweetness, reminiscent of bakery sugar cookies.
Now it’s time to add the dry ingredients. Just dump them into the wet mixture, and mix until a nice dough forms. Since the dough is pretty soft and sticky at this point, it’s best to wrap it up and chill it in the refrigerator for at least an hour before rolling it out.
While the dough is chilling, make up the filling. Just place some softened butter, brown sugar, and cinnamon into a bowl and stir everything together until smooth.
After the dough has chilled, place it onto a lightly-floured surface, and use a rolling pin to roll it out to roughly 9 by 13. Don’t get too caught up in the measurement. Just make sure that you’ve rolled it out into a rectangle, and the dough is thin enough to roll up.
Drop dollops of the brown sugar filling evenly over the dough, then use an offset spatula or the back of a spoon to evenly spread the filling across the entire surface of the dough. Now you’re ready to roll it up! Starting from the long side, gently lift the dough with your fingers and roll it up into a log. If the dough is sticking to the table, use a thin metal spatula to scrape/separate the dough from the surface as you roll it up.
Now that you’ve got your dough log, wrap it up, and chill it in the refrigerator for another hour. Please do NOT skip this step. Chilling the dough is absolutely essential for these cookies if you don’t want to end up with odd-looking pancakes. I mean, they’d still taste amazing, but they wouldn’t quite LOOK amazing…
After some beauty rest in the refrigerator, it’s time to bake the cookies! Just take the dough log out of the refrigerator, place it onto a cutting board, and cut the log into about 1/2-inch to 3/4-inch slices. Space them 2 inches apart on a parchment-lined baking sheet, and bake in the oven for 8-9 minutes. The cookies should look set and slightly golden along the bottom edges, but the centers will still look underdone.
Oh, and another thing! Make sure to return the dough that isn’t being baked BACK into the refrigerator. You want the dough to be COLD before placing it into the oven so that you don’t end up with flat edges and puffy middles.
While the cookies are baking you can make the cinnamon-sugar and cream cheese frosting. To make the cinnamon-sugar, just combine a couple of tablespoons of granulated sugar with a teaspoon of cinnamon in a small bowl. As for the cream cheese frosting, simply beat some softened butter, cream cheese, powdered sugar, vanilla, and a little bit of almond extract together until nice and fluffy.
Although cinnamon rolls are best when served warm, I prefer to let my cookies cool completely before icing them. This prevents the frosting from melting all over the place (not necessarily a bad thing), and they just look so much prettier! For these cinnamon sweeties, I used a small round tip and piped the frosting from the center out, using a spiral motion.
Once frosted, these cookies get their second helping of cinnamon sweetness with a dusting of cinnamon-sugar!
And BY THE WAY, these cookies were a TREMENDOUS hit at my Christmas gathering. People (especially my boyfriend) went absolutely bonkers for these Cinnamon Roll Cookies, so I highly HIGHLY recommend you try them out!
Cinnamon Roll Cookies
Ingredients
For the Cookie Dough:
- 2 ¼ cup all-purpose flour
- 1 teaspoon baking soda
- ½ teaspoon salt
- ¾ cup unsalted butter, softened
- 1 cup granulated sugar
- 2 eggs
- 1 teaspoon vanilla
- 1 (3.4 oz) package instant vanilla pudding mix (dry)
Cinnamon Brown Sugar Filling:
- 4 Tablespoons unsalted butter, softened
- ½ cup brown sugar
- 2 teaspoons cinnamon
Cream Cheese Frosting
- ½ cup butter, softened
- 6 ounces cream cheese, softened
- 1 teaspoon vanilla
- ¼ teaspoon almond extract
- 2 ½ cup powdered sugar
Cinnamon-Sugar
- 2 Tablespoons granulated sugar
- 1 teaspoon cinnamon
Instructions
Make the Dough:
- In a medium bowl, whisk the flour, baking soda, and salt together until combined; set aside.
- In the bowl of an electric stand mixer fitted with a paddle attachment, cream the butter until smooth. Add the sugar and mix on high for 3 minutes until light and fluffy. Add the eggs one at a time, mixing after each addition until combined. Add the vanilla, then stir in the pudding mix.
- With mixer set on low speed, slowly add the flour mixture into the wet mixture until everything has been incorporated. Cover bowl with plastic wrap and chill in the refrigerator for at least 2 hours, or up to 3 days.
Make the Filling:
- In a medium bowl combine the butter, brown sugar and cinnamon until smooth.
To Assemble:
- On a lightly-floured surface, roll the cookie dough out into a rectangle that's roughly 9x13-inches. Spread the filling evenly over the entire surface of the dough with an offset spatula or the back of a spoon.
- Starting from the long end, roll the dough up into a log. Wrap log in plastic wrap and place in the refrigerator for at least 1 hour.
- Preheat the oven to 350ºF, and line a baking sheet with parchment paper.
- Remove cookie log from refrigerator and cut 1/2" to 3/4" slices. Place cookie slices face up onto lined baking sheet and bake for 8-9 minutes.* While cookies are baking, make sure to keep the rest of the cookie log in the refrigerator until ready to slice and bake.
Make the Cinnamon Sugar:
- In a small bowl, combine the sugar and cinnamon; set aside.
Make the Cream Cheese Frosting:
- In the bowl of a stand mixer fitted with the paddle attachment, beat the cream cheese, butter, vanilla and almond extract together until combined. Add the powdered sugar and continue mixing until smooth and creamy. Transfer frosting to a pastry bag fitted with a small round tip.
- Using a spiral motion, pipe frosting onto cooled cookies. Sprinkle with cinnamon-sugar. Serve and enjoy!