This cinnamon roll cookie recipe makes soft vanilla cookies filled with sweet cinnamon swirls and topped with icing. They're a delicious cinnamon-roll-inspired cookie perfect for any cookie plate.
Make the cinnamon roll filling: Add butter, brown sugar, flour, and cinnamon to a medium bowl. Use a hand mixer to cream everything together until it becomes light and fluffy, about 3-5 minutes or until the sugar is almost dissolved.
3 tablespoons unsalted butter, 6 tablespoons light brown sugar, 1 tablespoon all purpose flour, 1 tablespoon ground cinnamon
Scoop ½ teaspoon sized portions of the filling onto the prepared baking sheet. Place in the freezer.
To make the cookie dough: To the bowl of your stand mixer, fitted with the paddle attachment, add butter and sugar. Beat until light and fluffy.
½ cup unsalted butter, ¾ cup granulated sugar
Add in eggs and vanilla. Beat again until combined.
2 large eggs, ½ teaspoon vanilla extract
Add flour, cream of tartar, baking soda, and salt. Mix until just combined.
1 ⅔ cups all purpose flour, ½ teaspoon cream of tartar, ½ teaspoon baking soda, ¼ teaspoon kosher salt
Sprinkle ⅓ of the frozen filling on top of the dough. Lightly fold it into the dough, careful not to overmix or blend the filling too much. (You still want pockets of cinnamon sugar instead of swirls).
Continue with the remaining ⅔ of filling in 2 more rounds of mixing.
Cover dough with plastic wrap and refrigerate for at least 1 hour.
Preheat oven to 375 F. Line baking sheets with parchment paper.
In a shallow dish, stir together the cinnamon and sugar for rolling.
½ cup granulated sugar, 1 teaspoon ground cinnamon
Using a 1 ½ tablespoon cookie scoop, scoop balls of cookie dough. Roll into a ball, then roll in the cinnamon sugar mixture.
Place about 2 inches apart on the prepared baking sheets. Leave plenty of space between each cookie to allow them to spread.
Bake for about 8-9 minutes, until cookies are lightly set but look a little doughy in the center. The filling might seep out a little bit, but if you use an upside down glass or a round cookie cutter around the perimeter of the cookie, you can swirl the cookies back into a round shape. Let cool completely on the baking sheet.
To make the icing: In a small bowl, whisk together the powdered sugar and milk.
½ cup powdered sugar, 1 tablespoon milk
Drizzle over the cooled cookies. Let icing set before serving.
Notes
Butter: You can substitute salted butter and omit the salt.
Salt: If you prefer to use table salt, use half the amount.
Flour: To properly measure the flour, weight it (click "metric" immediately above the ingredients for the weights) or sift/stir it to break it up, lightly spoon into a measuring cup, and level without packing.