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+ servings

Cinnamon Roll Cookies

You'll love this fun twist on classic cinnamon rolls -- full of buttery sugar cookie dough, plus a cinnamon sugar filling, and drizzled with homemade icing on top.
Prep Time 10 mins
Cook Time 10 mins
Chill Time 4 hrs
Total Time 4 hrs 20 mins
Course Dessert
Cuisine American
Servings 40
Calories 201 kcal

Ingredients
  

Sugar Cookies

  • 3 cups flour
  • teaspoons baking powder
  • 1 teaspoon fine sea salt
  • 1 cup unsalted butter room temperature
  • 4 ounces cream cheese softened
  • cups granulated sugar
  • 2 eggs room temperature
  • 2 tablespoons pure vanilla extract
  • ¾ teaspoon almond extract

Cinnamon Filling

  • 8 tablespoons butter melted
  • 4 tablespoons cinnamon
  • ¾ cup granulated sugar
  • ¾ cup brown sugar

Icing

  • 2 cups powdered sugar
  • ½ cup powdered sugar
  • 1 teaspoon pure vanilla extract
  • 4 to 5 tablespoons whole milk
  • 2 tablespoons melted Crisco original or butter
  • ½ teaspoon almond extract (optional)

Instructions
 

  • In a medium mixing bowl combine the flour, baking powder, and salt. Whisk together and set aside.
  • Using a stand mixer with a paddle attachment, add the butter and beat on medium until soft and fluffy, about two minutes. Add the cream cheese and continue to beat together until creamy and no lumps remain, about two minutes. Add the sugar and continue beating for another 1 to 2 minutes, or until fluffy. After stopping the mixer, scrape down sides with a rubber spatula. Turn mixer on medium speed and add the eggs, pure vanilla extract, and almond extract. Allow to mix until fluffy, about two minutes.
  • Slowly add the flour mixture to the butter mixer while on low speed and allow the mixture to slowly incorporate. Again, you'll want to be sure to scrape the sides down with a rubber spatula as needed. Do not over mix!
  • Divide the dough into two equal amounts, placing each in a piece of plastic wrap. Wrap plastic wrap around dough and refrigerate for 1 to 2 hours before rolling dough.
  • While your dough is chilling in the refrigerator, make your cinnamon filling. Combine all ingredients for the cinnamon filling in a small mixing bowl, stir together and then divide it in half and leave sitting out until chilling time for the dough is complete. Do not refrigerate the cinnamon filling so it stays soft and spreadable.
  • After chilling, remove dough from the fridge. Dust powdered sugar on your whole area (Silpat mat works best or a clean counter), dust the log and dust your hands. You can use a rolling pin but it’s easier to get your measurements quicker if you press it out by hand. Roll out one log at a time to roughly 8x9 inches. You want the rolled dough to be about ¼-inch thick. You don't want it to be too thick or it will lose the cinnamon roll shape while baking in the oven!
  • One log at a time, evenly spread ½ of the cinnamon mixture over the dough and get ready to roll! It’s important that whatever end you choose to be the inside of the roll has cinnamon all the way to the edge.
  • The opposite end (which will be the largest end part of the spiral within the roll, you want to leave a ¼-inch of area along the whole edge that does not have cinnamon filling on it. Leaving a bit of plain dough helps the dough glue to itself, completing the perfect spiral without having to deal with the butter in the cinnamon filling that could make it unstick in the baking process leaving you with a loose sloppy spiral. Tightly roll the dough into a 9-inch log. The center of the cookie is the start of the rolling process so go slowly, if it starts to crack or bunch, hold your hand over that area for a few seconds so the warmth from your hands warms the dough. By warming the dough it makes it more elastic so you can easily patch a little crack or hole with your fingers and continue rolling.
  • Once logs are tightly rolled, wrap in plastic wrap and chill for 2 hours.
  • Remove your cinnamon roll cookie logs and place them on a large cutting board. Preheat your oven now to 350°F. Serrated knives can work to cut the cookies but dental floss works best. Put a long piece of dental floss underneath the log in place to make a cut for a ½-inch cookie. Pull each piece of floss to the opposite side of the log, slicing gently through the dough. The gentleness of the floss cutting from one side to the other helps the log not to be squished down by the knife. If you do use a knife, be very gentle while pressing down to cut through the log. You want to work quick to ensure the logs are still chilled when you cut them. Cut each cookie to a thickness of about ½ -inch slice. Again, you don't want it to be thicker than that so it doesn't lose its shape.
  • Place each cookie on a silicone baking mat and place in the oven 2-inches apart from each other or about 12 on a sheet.
  • Bake for 8 to 11 minutes. Remove from the oven right as they start to brown on the edges. Do not overcook these cookies. They are best when they are taken out of the oven when they are still light and golden. They may appear to be undercooked but will continue cooking inside after removing from the oven.
  • Leave on the baking mat for 3 minutes before removing to a cooling rack.

For the Icing

  • While the cookies are cooling, make your icing. Whisk all icing ingredients together in a bowl. If the mixture is too thick for your liking, add additional milk ½ teaspoon at a time. Add powdered sugar 1 teaspoon at a time if it is too thin until desired consistency is reached.
  • Drizzle the icing over the cookies

Notes

TIP: Flipping the cinnamon roll cookie dough over while rolling will prevent the dough from sticking to your silicone mat. I also rolled out the dough on a floured surface to help keep it from sticking.
TIP: These cookies need to be placed in the oven while still cold. This is what helps them to maintain their rolled shape.
TIP: Leave the cookies on the wire rack while drizzling the icing so that it doesn't pool around the cookies.

Nutrition

Sodium: 94mgCalcium: 27mgVitamin C: 1mgVitamin A: 267IUSugar: 21gFiber: 1gPotassium: 47mgCholesterol: 30mgCalories: 201kcalTrans Fat: 1gMonounsaturated Fat: 2gPolyunsaturated Fat: 1gSaturated Fat: 5gFat: 9gProtein: 2gCarbohydrates: 29gIron: 1mg