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A stack of six cookies with white icing drizzle sits on a metal plate, surrounded by more cookies and a glass of milk in the background.

Gluten Free Cinnamon Roll Cookies

Soft gluten-free cinnamon roll cookies filled with homemade brown sugar cinnamon pieces and rolled in cinnamon sugar. These free form drop cookies have all that buttery cinnamon flavor without rolling or slicing the dough, with a sweet cream cheese glaze for finishing.
Prep Time 15 minutes
Cook Time 14 minutes
Chill Time 30 minutes
Total Time 59 minutes
Servings 16

Ingredients

Cinnamon Chip Filling

  • 4 Tablespoons (56 g) unsalted butter room temperature
  • ½ cup (110 g) brown sugar
  • 1 Tablespoon (8 g) cinnamon

Cinnamon Cookie Dough

  • ¾ cup (170.25 g) unsalted butter room temperature
  • ⅓ cup (100 g) granulated sugar
  • ½ cup (110 g) brown sugar
  • 1 egg
  • 1 ½ teaspoons vanilla extract
  • 2 cups (256 g) 1:1 gluten-free flour with xanthan gum
  • ½ teaspoon baking soda
  • ½ teaspoon baking powder
  • ½ teaspoon kosher salt

For Rolling

  • ¼ cup (50 g) granulated sugar
  • 1 Tablespoons (8 g) cinnamon

Cream Cheese Glaze (optional)

  • 2 ounces (56.7 g) cream cheese set out at room temperature for 1 hour
  • 2 Tablespoons (29.57 ml) milk
  • ½ cup (60 g) powdered sugar
  • ½ teaspoon vanilla extract

Instructions

Cinnamon Chip Filling

  • In a large bowl or stand mixer, add all the ingredients. Beat well, scraping down the sides, until completely smooth. Line a baking sheet with parchment paper. Spread out the filling and use a knife to score into small squares.
  • Freeze for 20 to 30 minutes while you prepare the dough. The longer they freeze the less chance for the filling to ooze out. Remove from the freezer and break into little pieces.

Cinnamon Cookie Dough

  • In the same large bowl or stand mixer (no need to wash it), add the butter and both sugars. Cream the softened butter and sugar with an electric mixer or stand mixer on medium for 2 minutes. Add the egg and vanilla. Beat for another 2 minutes scraping down the side of the bowl.
  • Mix the remaining dry ingredients in a small bowl. Slowly add the butter and sugar mixture while mixing on low speed until fully combined. Stir in the cinnamon pieces by hand.
  • Using a large cookie scoop, roll each scoop into a ball and place on a baking sheet. Chill for 30 minutes. Preheat the oven to 350 F degrees while the dough is chilling.
  • Mix together the sugar and cinnamon for rolling. Roll each ball of dough in the mixture. Place 2 inches apart on an insulated cookie sheet.
  • Bake the cookies for 12 to 14 minutes. If they spread while baking, use a large round cookie cutter place over the cookie and swirl around to reform the cookies. Cool on the cookie sheet for 5 minutes before moving to a wire rack.

Cream Cheese Glaze

  • Whisk together all the ingredients and drizzle over the cooled cookies.

Equipment

  • cookie sheet

Notes

Dairy Free Option: Use your favorite dairy free stick butter in both the cinnamon filling and cookie dough. For the glaze, use dairy free cream cheese and your preferred unsweetened dairy free milk. You can also skip the glaze entirely, which is what I usually do for everyday cookies.