Cinnamon Roll Sugar Cookies

Close-up top view of Cinnamon Roll Cookies on a wire cooling rack.

These dreamy Cinnamon Roll Sugar Cookies feature a soft vanilla sugar cookie base, layered with a buttery brown sugar and cinnamon topping, all topped off with a decadent swirl of the best cream cheese frosting!

Author Amber Brady

Prep Time 30

Cook Time 10

Total Time 40

Yields cookies

Ingredients

Sugar Cookies

2 ¾ cups (330 g) all-purpose flour, (stir, spoon & level)
¼ tsp baking soda
¼ tsp cream of tartar
½ tsp salt
½ cup (113 g) unsalted butter, (1 stick) room temperature
10 Tbsp (125 g) granulated sugar, (½ cup plus 2 Tbsp)
6 Tbsp (45 g) powdered sugar
6 Tbsp (90 ml) oil, (canola/vegetable)
1 Tbsp water
1 large egg
½ tsp vanilla extract
2 Tbsp (25 g) *extra granulated sugar, (for flattening the cookies)

Cinnamon Brown Sugar Topping

6 Tbsp (85 g) unsalted butter, room temperature/softened
½ cup (100 g) light brown sugar, gently packed
¼ cup (30 g) all-purpose flour, (stir, spoon & level)
2 Tbsp ground cinnamon

Cream Cheese Frosting

4 oz (113 g) block-style cream cheese, COLD
4 Tbsp (57 g) unsalted butter, room temperature
½ cup (60 g) powdered sugar
½ tsp vanilla extract

Instructions

Preheat oven to 350 degrees Fahrenheit. Line two half sheet pans with silicone baking mats or parchment paper. Set aside.
SUGAR COOKIES: In a medium bowl, combine the flour, baking soda, cream of tartar, and salt. Set aside.
In the bowl of a stand mixer with the paddle attachment, cream the butter, granulated sugar, and powdered sugar until smooth. Then add the oil, water, egg, and vanilla. Mix well, scraping the bowl as needed.
Add the dry ingredients all at once to the wet ingredients, and mix until everything comes together.
Use a #30 cookie scoop (about 2 Tbsp of cookie dough) to scoop dough balls onto the prepared baking sheets about 2-3 inches apart (no more than 9 per tray). You should get 18 cookies on two trays. Roll dough balls with hands until smooth and round.
Put 2 Tbsp granulated sugar in a small bowl. Dip the bottom of a cup into the bowl of sugar, and press it into the center of each dough ball until about ½-inch thick, creating a well in the center of the dough. (You may find it helpful to rock the cup in a circular motion.) Set cookies aside.
CINNAMON BROWN SUGAR TOPPING: Stir together the butter, brown sugar, flour, and cinnamon in a medium bowl with a spoon until combined well. (TIP: It helps to have fairly soft butter, and to cut the butter into smaller pieces first.)
Divide the cinnamon topping between the 18 cookies. (I used a heaping teaspoon; about 1 ½ tsp per cookie.) Use your finger to spread the cinnamon topping towards the edge of the cookies, but still inside the well. (So the topping doesn't melt over the edges.)
Bake the cinnamon roll sugar cookies at 350˚F for 9-10 minutes. Do not over-bake. The cookies will not brown at all on the edges, but will look matte instead of shiny. Allow the cookies to cool on the tray completely.
CREAM CHEESE FROSTING: While cookies cool, prepare the frosting by beating the cream cheese and butter together in a large bowl with an electric hand mixer until smooth. Add the powdered sugar and vanilla and mix until combined.
Place cream cheese frosting in a pastry bag fitted with a Wilton #12 round tip. Pipe a thin layer of frosting into a swirl on top of each cookie starting from the middle and working your way towards the edges. Make sure to leave a little space in-between to show the layer of cinnamon underneath. Enjoy immediately, or cover and refrigerate for later.

Notes

Do not leave cookies out at room temperature for more than 2 hours.
STORAGE: Store cookies in an airtight container or on a plate covered tightly with plastic wrap. Keep refrigerated for up to 5 days.
TO FREEZE: Place cookies onto a baking sheet in a single layer and freeze until frosting is frozen solid (about 1-2 hours). Once firm, transfer cookies to a freezer-safe container with parchment paper separating any layers and freeze for up to 3 months. Thaw in fridge overnight before enjoying.

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