Before I dive into these delicious little cinnamon roll cookies, I want to tell you a story. I went to a very small rural elementary school that was one of the oldest elementary schools in the state of Oregon, and at the time it was actually its own school district due to some very old legislation that was accidentally still in place. Because of this, the nutritional cafeteria requirements that applied to the rest of the schools in Oregon didn’t apply to us, which resulted in some very decadent childhood lunches. Did you know that a “hot” lunch for a 7-year old could be comprised of a single homemade cinnamon roll the size of a child’s head? We also had homemade “wiener dogs”, which were hot dog wieners wrapped in a ton of bread dough, and “pizza” which was a tray of thick focaccia-like bread covered with tomato sauce and cheese and baked in the oven until bubbly and delicious.

Cinnamon Roll Cookies

My mom always packed our lunches because it was healthier and more cost-effective (she was feeding three little mouths on a daily basis), and I was happy with that for the most part. However, when cafeteria posted the hot lunch schedule on the wall and I saw that it was going to be a cinnamon roll day, I’d BEG my mother to let me get a hot lunch instead. However many rooms I could vacuum or bathroom mirrors I could clean, I would barter anything to get my tiny hands on one of those giant, fluffy, glaze-soaked cinnamon rolls. It would usually work, and I’d stuff myself with the giant cinnamon roll at lunch, surge into a sugar high, and ride it until the afternoon when I suddenly felt like it was time for a nap. Eventually the Hillsboro school district incorporated our school, and the food changed a lot. They brought in a salad bar, which was good, but gone were the days of epic cinnamon rolls and wiener dogs. The cafeteria was never quite the same after that, but my love of cinnamon rolls remained unchanged.

Cinnamon Roll CookiesAs such, I was brainstorming delicious and adorable cookies to make for the holidays, and suddenly was struck by the idea of cinnamon roll cookies (I think my mental pathway went sliceable cookie -> swirly log cookie -> cinnamon roll cookies -> GLAZE!) The vanilla cookie dough is a simple sugar cookie base but with light brown sugar instead of regular granulated sugar for a warmer, more chocolate-chip-cookie-like taste. For the cinnamon swirl, I pureed together chopped dates, pecans, vanilla extract, butter, and a LOT of cinnamon, and then stirred in some flour to keep it nice and firm. The assembly is really easy, and you can watch the video above the recipe to see how to make these little swirly guys. Once they’re baked and cooled, just drizzle them with a bit of vanilla glaze and you’re well on your way to riding a cinnamon roll rocket straight into the sky. They’re seriously *that* good. I hope you guys enjoy them + have a wonderful holiday and a very merry Christmas, and if you need more cookie inspiration I have some almond-y Greek butter cookies on the blog, too!

P.S.

My 2019 creative mastermind is open for registration, and I’d love to have you join! You can read all about it here, but the jist of it is that you’ll enjoy a 6-month intensive getting your creative business roaring + learning from the experiences of fellow amazing creative women. And I once more wanted to gently suggest that if you’re looking for a last-minute gift, you might consider my cookbook First We Eat 🙂 And if you’re *really* behind on holiday shopping, you can check out my gift guide for some last-minute recommendations. You got this!!

Cinnamon Roll Cookies

Cinnamon Roll Cookies

These delicious cinnamon roll cookies are made from a vanilla sugar cookie dough and filled with a date, pecan, vanilla bean, butter, and cinnamon filling. Make sure to watch the video above for instructions on assembling the cookie log. I also recommend using a sandwich-sized ziplock bag with a very small hole cut off one of the corner to drizzle the glaze over the cookies with precision.

Course Dessert
Keyword cookies
Servings 36 cookies
Calories 123 kcal

Ingredients

Vanilla Dough

  • 3/4 cup light brown sugar
  • 1/4 cup powdered sugar
  • 1/3 cup plus 1 tablespoon unsalted butter room temperature
  • 1 egg
  • 1 tablespoon whole milk
  • 2 teaspoons vanilla extract
  • 2 cups flour
  • 3/4 teaspoon flake sea salt
  • 1/4 teaspoon baking soda

Cinnamon Filling

  • 1 cup chopped pitted dates
  • 1/2 cup chopped pecans
  • 1/4 cup plus 1 tablespoon unsalted butter room temperature
  • 1/4 cup light brown sugar
  • 1 tablespoon cinnamon
  • 1 teaspoon vanilla extract
  • 1/4 teaspoon flake kosher sea salt
  • 1/2 cup flour

Glaze

  • 1 cup confectioners sugar sifted
  • 2 teaspoons milk
  • 1 teaspoon honey
  • 1/2 teaspoon vanilla extract

Instructions

Vanilla Dough

  1. In the bowl of a stand mixer fitted with the paddle attachment, beat together the light brown sugar, powdered sugar, and butter at medium speed until smooth and fluffy. Add the egg, milk, and vanilla and continue mixing until combined.

  2. In a small bowl, whisk together the flour, salt, and baking soda to combine. Empty the flour mixture into the butter mixture and reduce the speed to low, mixing until they are *just* combined. Form the dough into a ball and then pat it out into a rough rectangle, cover it, and refrigerate it for 1 hour.

Cinnamon Filling

  1. In food processor or blender, blend together all the ingredients except the flour until smooth. Transfer the mixture to a bowl or stand mixer and stir in flour by hand or at low speed until *just* combined. Set aside at room temperature.

Assembly

  1. Roll out the vanilla dough into a 12 x 9-inch rectangle on a lightly floured piece of parchment paper. Spread the surface with cinnamon filling, going all the way to the edges of the rectangle. Roll the dough up from the long edge into a log, using the paper to help you, and using a metal spatula if needed to keep the dough from sticking to paper.

  2. Once rolled, discard the paper and roll the log a little more on clean work surface to make it 16 inches long and a uniform cylinder. Cover and refrigerate for 90 minutes.

  3. Preheat the oven to 400 degrees and line 3 baking sheets with parchment paper. Slice the log into 1/4-inch thick slices and place each cookie slice on a baking sheet with about 2 inches of space between the cookies. Once all the sheets are filled with cookies, place the baking sheets in the oven and bake until the cookies *just* start to turn a very faint gold around the edges, about 10 minutes.

  4. Remove the pan from the oven and allow the cookies to cool for 10 minutes before transferring them to a wire rack to cool completely.

Glaze

  1. Whisk together all ingredients until smooth. To drizzle the glaze with precision, empty into a sandwich-sized ziplock bag and seal it. Cut off a VERY small tip of the corner of the bag (it's better to be too small than too big, you can always cut a bigger hole if you need to). Squeeze the bag to get the icing to drizzle out in a consistent stream. You can also drizzle it by hand with a spoon for a less precise appearance.

  2. Drizzle a zig-zag pattern over each cookie and allow the cookies to rest for 15 minutes to set and harden the icing before touching and serving. These will keep in an airtight container in the refrigerator for up to 1 week.

Nutrition Facts
Cinnamon Roll Cookies
Amount Per Serving
Calories 123 Calories from Fat 36
% Daily Value*
Fat 4g6%
Saturated Fat 2g13%
Cholesterol 12mg4%
Sodium 76mg3%
Potassium 52mg1%
Carbohydrates 20g7%
Sugar 12g13%
Protein 1g2%
Vitamin A 100IU2%
Calcium 13mg1%
Iron 0.6mg3%
* Percent Daily Values are based on a 2000 calorie diet.

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