Description

These Cinnamon Roll Sugar Cookies combine the sweet, spicy flavors of classic cinnamon rolls with the crisp, buttery texture of sugar cookies. Soft, chewy, and generously swirled with cinnamon sugar filling, these cookies are perfect for a comforting treat or holiday baking. The dough is layered with cinnamon sugar, lightly folded to create pockets of melted cinnamon flavor, then baked to golden perfection.

Ingredients

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Cinnamon sugar filling:

4 tablespoons unsalted butter, softened
1/3 cup brown sugar, packed
1 1/2 tablespoons all-purpose flour
2 1/2 teaspoons ground cinnamon
Pinch salt

Cookies:

1 cup unsalted butter, softened but still cool to the touch
1 1/3 cups granulated sugar
1 3/4 teaspoons pure vanilla extract
1 large egg
1 large egg yolk
2 3/4 cups all-purpose flour
3/4 teaspoon baking powder
1 teaspoon cornstarch
1/4 teaspoon salt

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Instructions

Preheat oven and prepare baking sheets: Preheat your oven to 350°F (175°C) and place racks near the center. Line two baking sheets with parchment paper and set aside for baking later.
Make cinnamon sugar filling: Mix together softened butter, brown sugar, flour, ground cinnamon, and salt with a small rubber spatula or fork until fully combined. Place the mixture in the freezer for about 10 minutes to firm up while you prepare the cookie dough.
Prepare cookie dough base: Using a hand mixer or stand mixer fitted with the paddle attachment, beat the softened butter and granulated sugar until the mixture becomes light and creamy. Add vanilla extract, whole egg, and egg yolk, then beat again until everything is incorporated, scraping down the bowl sides as needed.
Combine dry ingredients: In a separate bowl, whisk together all-purpose flour, baking powder, cornstarch, and salt. Gradually add this dry mixture to the wet ingredients, beating just until combined to form your cookie dough.
Divide and layer dough: Remove half of the dough and set aside. Spread the remaining half evenly across the bottom of the mixing bowl. Take the cinnamon sugar filling from the freezer and using two spoons, scatter small teaspoon-sized pieces evenly over the dough layer in the bowl.
Add second dough layer and topping cinnamon: Spread the reserved half of the cookie dough as an even layer on top of the cinnamon sugar pieces. Then again distribute the remaining cinnamon sugar mixture over this dough layer in small pieces. Your bowl should now contain two cookie dough layers separated by cinnamon sugar.
Fold cinnamon sugar into dough: Gently fold and stir the dough just enough to create swirled pockets of cinnamon sugar—two folds followed by one or two manual stirs with a rubber spatula to keep some chunks intact. Avoid using an electric mixer here to prevent overmixing.
Scoop and chill dough: Using a two-tablespoon cookie scoop, portion the dough ensuring each scoop has cinnamon sugar mixed in. Place dough balls on a plate and freeze for 10 minutes to firm up the butter, which helps the cookies maintain their shape when baking.
Arrange and bake cookies: Space dough balls a couple inches apart on the prepared baking sheets. For thicker cookies, leave them as rounded mounds; for thinner cookies, gently pat the dough balls flatter. Bake in the preheated oven for 10-12 minutes until edges start to brown and centers remain slightly underbaked.
Cool and shape cookies: Some cookies may spread unevenly due to melted cinnamon sugar pockets. To achieve perfectly round cookies, you can reshape them slightly as soon as they come out of the oven while still soft (see notes). Transfer baking sheets to wire racks and allow cookies to cool completely, during which they will firm up.

Notes

You can shape cookies immediately after baking by gently pressing or reshaping the warm cookies to a round form using the back of a spoon or spatula.
When measuring flour, spoon it into your cup and level it off for accuracy; this helps prevent overly dense cookies.
If you have leftover dough, refrigerate it rather than freezing, and bake it once the baking sheets have cooled.
Chilling the dough before baking is key to controlling cookie spread and maintaining nice texture.
The layered folding technique creates spots of cinnamon sugar which melt and caramelize during baking for the signature cinnamon roll flavor.

Nutrition

Serving Size: 1 cookie
Calories: 180
Sugar: 14g
Sodium: 90mg
Fat: 9g
Saturated Fat: 5g
Unsaturated Fat: 3g
Trans Fat: 0g
Carbohydrates: 22g
Fiber: 1g
Protein: 2g
Cholesterol: 40mg