Can't decide between a cookie and a cinnamon roll? No need to choose with these Cinnamon Roll Cookies! Sweet cinnamon filling rolled into buttery sugar cookie dough, baked and topped with a drizzle a vanilla icing.


  • 3/4 cup unsalted butter (softened)
  • 3/4 cup granulated sugar
  • 1 egg
  • 1 teaspoon vanilla extract
  • 2 1/4 cups all purpose flour
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 6 tablespoons light brown sugar (packed)
  • 1 tablespoon ground cinnamon
  • 1/8 teaspoon salt
  • 2 tablespoons unsalted butter (melted)
  • 2/3 cup powdered sugar (sifted)
  • 1 pinch salt
  • 1/2 teaspoon vanilla extract
  • 4 teaspoons milk


  1. While the cookie dough chills, prepare the cinnamon sugar filling. In a medium bowl, whisk together the brown sugar, cinnamon, salt, and melted butter until thoroughly combined. Set aside.
  2. Remove the chilled cookie dough from the refrigerator. Generously dust a clean work surface with flour.
  3. Unwrap the cookie dough and place on the work surface. Using a rolling pin, roll the dough into a rectangle approximately 14” x 9”, to ¼” thickness.
  4. Spread the rectangle of cookie dough with an even layer of cinnamon sugar filling.
  5. Working gently, tightly roll the cookie dough lengthwise, into a 14” log.
  6. Cover the log with plastic wrap, and refrigerate for 1 hour.
  7. Line two baking sheets with silicone baking mats or parchment paper. Set aside.
  8. Preheat the oven to 350° F.
  9. Remove the log of cookie dough from the refrigerator. Using a very sharp knife, slice the log into ½” thick cookies. Place the slices onto the baking sheets roughly 1 ½” apart.
  10. Transfer the baking sheets to the preheated oven. Bake the cookies for 11-12 minutes, until the bottom edges are lightly browned.
  11. Remove the baking sheets from the oven. Allow the cookies to cool for 5 minutes on the sheets, then transfer them to cooling racks to cool completely before icing.
  12. To make the glaze, place the powdered sugar and salt in a medium bowl.
  13. Add the vanilla and 3 teaspoons of milk. Whisk slowly to combine. If the icing is too thick, add another ½-1 teaspoon of milk.
  14. Use a spoon to drizzle thin strands of icing across each cookie. Allow to set for 10-15 minutes before serving.
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