Cinnamon Roll Sugar Cookies (Soft & Chewy)

These soft and chewy cinnamon roll sugar cookies combine everything you love about classic cinnamon rolls, snickerdoodles and soft sugar cookies. Each buttery cookie is filled with beautiful brown sugar-cinnamon swirls, with lightly golden edges and a tender center. They are perfect for fall baking, Christmas cookie trays or a cozy coffee break.

Prep Time: 25 minutes | Chill Time: 10 minutes | Bake Time: 10–12 minutes | Total Time: 46 minutes | Yield: 20 cookies | Oven: 350°F (175°C)

Why You’ll Love Cinnamon Roll Cookies

• Real cinnamon roll flavor without yeast, rising or rolling.
• Pretty marbled swirls of brown sugar and cinnamon in every bite.
• Soft and chewy texture thanks to the extra egg yolk and cornstarch.
• Perfect for the holidays, cookie exchanges and fall baking.

Ingredients

For the Cinnamon Sugar Filling

• 4 tablespoons (56 g) unsalted butter, softened
• 1/3 cup (70 g) packed brown sugar
• 1 1/2 tablespoons all-purpose flour
• 2 1/2 teaspoons ground cinnamon
• 1 pinch of salt

For the Sugar Cookie Dough

• 1 cup (2 sticks / 226 g) unsalted butter, softened but still cool
• 1 1/3 cups (265 g) granulated sugar
• 1 3/4 teaspoons pure vanilla extract
• 1 large egg, at room temperature
• 1 large egg yolk
• 2 3/4 cups (345 g) all-purpose flour
• 3/4 teaspoon baking powder
• 1 teaspoon cornstarch
• 1/4 teaspoon salt

How to Make Cinnamon Roll Sugar Cookies

1. Preheat the oven. Preheat the oven to 350°F (175°C) with the racks near the center. Line two large baking sheets with parchment paper.
2. Make the cinnamon filling. In a small bowl, mix the softened butter, brown sugar, flour, cinnamon and salt until smooth.
3. Chill the filling. Freeze the cinnamon mixture for about 10 minutes while you make the dough, so it stays in distinct swirls.
4. Cream the butter and sugar. Beat the butter and granulated sugar for 2–3 minutes until light and creamy.
5. Add the wet ingredients. Mix in the vanilla, egg and egg yolk, scraping down the bowl as needed.
6. Mix the dry ingredients. In another bowl, whisk the flour, baking powder, cornstarch and salt.
7. Make the dough. Gradually add the dry ingredients to the butter mixture, mixing just until a soft, thick dough forms.
8. Layer the filling. Remove half of the dough. Spread the rest across the bottom of the bowl and dot it with teaspoon-sized pieces of half the chilled filling.
9. Add the second layer. Press the reserved dough on top and scatter the remaining filling over it.
10. Fold gently. With a spatula, fold the dough over itself about twice, then stir 1–2 times. Stop while visible cinnamon ribbons remain.
11. Shape the cookies. Scoop about 2 tablespoons of dough per cookie, making sure each one has some filling, and roll into tall balls.
12. Chill again. Freeze the dough balls for 10 minutes to prevent spreading.
13. Bake. Place them 2 inches apart and bake for 10–12 minutes, until the edges are just golden and the centers look slightly soft.
14. Reshape if needed. Right out of the oven, swirl a round cookie cutter around any uneven cookies to make them perfectly round.
15. Cool. Let the cookies cool completely on the baking sheets. They will set into a soft, chewy texture.

Pro Tips

• Keep the filling cold so you get clear cinnamon ribbons instead of one uniform color.
• Don’t overmix after adding the filling. A few gentle folds create the marbled look.
• Measure the flour correctly with the spoon-and-level method to avoid dry cookies.
• For thicker cookies, keep the dough balls tall and bake them straight from the freezer.
• Underbake slightly. The centers finish setting as the cookies cool.

Optional Cinnamon Roll Glaze

For a true cinnamon roll finish, whisk 1 cup (120 g) powdered sugar with 2 tablespoons milk and 1/2 teaspoon vanilla, then drizzle over the cooled cookies. You can also use a cream cheese glaze.

How to Store and Freeze

Store the cookies in an airtight container at room temperature for up to 5 days. Freeze baked cookies or unbaked dough balls for up to 3 months and bake the dough straight from frozen, adding 1–2 minutes.

Frequently Asked Questions

Why did my cinnamon swirl disappear?

The filling was too soft or the dough was overmixed. Chill the filling well and fold only a few times.

Can I make the dough ahead?

Yes. Refrigerate the shaped dough balls for up to 2 days, or freeze them for up to 3 months.

More Cookie Recipes to Try

• Butter Pecan Cookies
• Cream Cheese Sugar Cookies
• Whipped Shortbread Cookies
• Cinnamon Roll Poke Cake