Cinnamon Roll Cookies

5 from 3 votes

A simple sugar cookie base with a cinnamon filling and a sweet icing glaze. It is like your favorite cinnamon roll and cookie got married!

Prep Time10

Cook Time10

Chill Time1

Total Time1 20

Course: Dessert

Cuisine: American

Servings: cookies

Calories: 195kcal

Author: Jennifer Fishkind

Ingredients

Sugar Cookies

3 cups Flour
1½ tsp Baking Powder
1 tsp Fine Sea Salt
1 cup Unsalted Butter (room temperature is important)
4 ounces Cream Cheese softened
1½ cups Granulated Sugar
2 Eggs room temperature
2 tbsp Pure Vanilla Extract
¾ tsp Almond Extract

Cinnamon Filling

1 stick Melted Butter
4 tbsp Cinnamon
¾ cup Granulated Sugar
¾ cup Brown Sugar

Icing

2 cup + ½ cup Powdered Sugar
1 tsp Pure Vanilla Extract
4-5 tbsp Whole Milk
2 tbsp Melted Crisco (original or butter)
½ tsp Almond Extract Optional

Instructions

In a medium mixing bowl combine the flour, baking powder, and salt. Whisk together and set aside. (optional) Sift out any clumps.
Using a stand mixer with a paddle attachment, add the butter and beat on medium until soft and fluffy, for no less than 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 2 minutes, until fluffy. After scraping down sides with a rubber spatula of your mixer bowl, turn the 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 mixture while on low stir speed and allow the mixture to slowly incorporate. Again, be sure to scrape the sides down with a rubber spatula as needed. Do not over mix!
Divide the dough into two equal amounts (logs), placing each in a piece of plastic wrap. Wrap plastic wrap around each dough mixture and refrigerate for 1 hour before rolling out the 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 (silicon baking 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!
HELPFUL TIP: Flipping the dough over periodically and powdering your hands or roller, while rolling will prevent the dough from sticking to your silicone mat or surface.
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 1/4 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 degrees. 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.
HELPFUL TIP: These cookies need to be placed in the oven while still cold! This is what helps them to maintain their rolled shape!
a. Place each cookie on a silicone baking mat and place in the oven 2-inches apart from each other or about 10 on a sheet for space to spread out a bit.
b. Bake at 350 degrees for 8-10 minutes. Remove from the oven right as they start to just slightly brown on the edges. Do not overcook. They are best when they are taken out of the oven when they are still very light and golden. They may appear to be undercooked but will continue cooking inside after removing from the oven.
c. Leave on the baking mat for 3 minutes before gently removing to a cooling rack with a spatula
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 1/2 teaspoon at a time. Add powdered sugar 1 tsp at a time if it is too thin, until desired consistency is reached.Drizzle the icing over the cookies. Squeeze bottles work very efficiently to apply the icing very neatly and thinly so the adorable cinnamon roll spiral still peaks through the icing! Enjoy!

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