Cinnamon Roll Sugar Cookies
The softest, most delicious sugar cookies topped with a cinnamon sugar filling, then rolled and cut into slices, and baked to perfection.
Ingredients
Sugar Cookie Dough:
- 1 cup (2 sticks) butter room temperature
- 1 cup (7.5 ounces) granulated sugar
- 3 large eggs
- 2 teaspoons pure vanilla extract
- 3 ½ cups (17.5 ounces) all-purpose flour see note
- 1 tablespoon baking powder
Filling:
- 6 tablespoons butter
- ⅔ cup granulated sugar
- 3 tablespoons ground cinnamon
Icing:
- 1 ½ cup powdered sugar
- ¾ teaspoon pure vanilla extract
- 2 to 2 ½ tablespoons milk
Instructions
For Sugar Cookie Dough:
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In a large mixing bowl or the bowl of a stand mixer, cream the butter and sugar together for about 3 to 4 minutes until the mixture is light and fluffy. Add eggs one at a time and mix well after each addition. Stir in the vanilla extract and mix.
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In a medium bowl combine the flour and baking powder. Add the dry ingredients slowly to the wet ingredients, mixing well until completely mixed in.
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Cover cookie dough completely with plastic wrap and chill in the refrigerator for 2 hours or up to a week in advance (see note).
Assembling the Cookies:
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Flour the counter and rolling pin well. Divide the dough into half and roll each half into a ¼-inch thick rectangle (about 14-inches by 9-inches). Dough should be close to an even thickness everywhere.
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In a small microwavable bowl, add filling ingredients: butter, granulated sugar, and cinnamon. Melt in 30-second ingredients in the microwave stirring in between until butter has completely melted. Stir well and pour half of filling over sugar cookie dough. Spread filling evenly over cookie dough, using your hands, if needed to spread evenly.
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Starting with one long end, roll up dough tightly like a cinnamon roll. Moisten the lower ½-inch border of dough using your fingers dipped in a little water and press to seal into a log. Wrap in plastic wrap and chill in the refrigerator for 2 hours. Repeat with other half of dough.
Baking the Cookies:
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Preheat oven to 375 degrees F. Line 2 cookie sheets with parchment paper and set aside.
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Using a sharp knife (I use a serrated knife), slice the dough into 1/4-inch slices, making about 24 cookies per log.
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Place cookies 2 inches apart on prepared baking sheets and bake for 8-9 minutes or until cookies are barely set but not brown. If you wait until they brown, they will be overbaked.
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Let the cookies cool for 1-2 minutes on the baking sheet before transferring to a wire rack to cool completely.
For the Icing:
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Prepare the icing by whisking together the powdered sugar, the vanilla, and the milk until smooth. The icing should be thick, but still pourable. Add more powdered sugar or milk if necessary to reach thick, pourable consistency. Using the whisk or a fork, drip icing over cooled cookies. Let icing set for about 10 to 15 minutes to harden.
Recipe Notes
1. How you measure the flour will make a huge difference in the taste and texture of these cookies. Too much flour and they will be thick and crumbly and not spread out properly. Just the right amount of flour and they will be perfect - thin and chewy and delicious. If you don’t have a scale (and I recommend you get one because they are a lot more accurate) just use a super light hand in the flour measuring. Don’t pack it in. Fluff it first then scoop it with a spoon into the measuring cup.
2. To speed up the chilling process I sometimes stick the cookie dough in the freezer. Since every freeze is different, you will have to experiment for how long. My older freezer took around 30 minutes, but I'm finding that is too long for my newer freezer. Probably around 15 to 20 minutes is better.
2. I like to ice the cookies on the cooling rack with something underneath to catch the drips.
3. Cookies can be stored at room temperature for up to 3 days. They also freeze well for up to a month.