Soft and Chewy Cinnamon Roll Sugar Cookies with a Sweet Cinnamon Swirl

These Cinnamon Roll Sugar Cookies are the dream cookie for cinnamon lovers! Imagine a perfect fusion of cinnamon rolls, snickerdoodles, and sugar cookies, resulting in soft, chewy cookies with an irresistible brown sugar-cinnamon swirl marbled throughout. They’re warm, aromatic, and utterly delicious. With the perfect balance of sweetness and spice, these cookies offer the comfort of a cinnamon roll in every bite while retaining the lightness of a classic sugar cookie.

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Whether you’re hosting a gathering, looking for a fun weekend baking project, or just craving something sweet to snack on, these cinnamon roll sugar cookies are sure to please. Let’s dive into this delightful treat and see how you can create them at home!

Ingredients Breakdown

Before we get into the step-by-step instructions, let’s take a look at the key ingredients that make these Cinnamon Roll Sugar Cookies so special.

For the Cinnamon Sugar Filling:

• 4 tablespoons unsalted butter (softened): This forms the creamy base for the cinnamon-sugar filling, helping it bind together.
• ⅓ cup brown sugar (packed): Adds the deep, rich sweetness essential for a true cinnamon roll flavor.
• 1½ tablespoons all-purpose flour: Helps the filling hold together as it melts and swirls through the cookie dough.
• 2½ teaspoons ground cinnamon: The star of this recipe! This warm spice gives the cookies their cinnamon roll flavor.
• Pinch salt: Balances the sweetness and enhances the flavors.

For the Cookies:

• 1 cup unsalted butter (softened but still cool to the touch): This is the base for the cookie dough, providing structure and flavor.
• 1 ⅓ cups granulated sugar: Sweetens the cookies and helps them crisp up at the edges when baked.
• 1 ¾ teaspoons pure vanilla extract: Adds a lovely vanilla undertone to complement the cinnamon.
• 1 large egg: Acts as a binder and helps create a tender texture.
• 1 large egg yolk: Adds richness and moisture to the cookies.
• 2 ¾ cups all-purpose flour: The bulk of the cookie dough. Proper flour measurement is essential for the right texture (see the note below on how to measure flour properly).
• ¾ teaspoon baking powder: Helps the cookies rise and gives them a soft, tender crumb.
• 1 teaspoon cornstarch: Helps the cookies stay chewy and soft.
• ¼ teaspoon salt: Enhances all the other flavors in the dough.

Step-by-Step Instructions:

1. Prepare the Cinnamon Sugar Filling:

• Mix the ingredients: In a small bowl, combine softened butter, brown sugar, flour, cinnamon, and a pinch of salt. Use a small rubber spatula or fork to mix until everything is well combined.
• Freeze the mixture: Place the cinnamon sugar mixture in the freezer for about 10 minutes. This helps firm up the butter and makes it easier to scoop and layer into the cookie dough later.

2. Make the Cookie Dough:

• Cream the butter and sugar: In a stand mixer or using a hand mixer, beat the butter and granulated sugar together until the mixture is light and creamy.
• Add the wet ingredients: Mix in the vanilla extract, egg, and egg yolk. Continue beating until well combined.
• Combine the dry ingredients: In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt.
• Add the dry ingredients to the wet: Gradually add the dry ingredients to the butter-sugar mixture, mixing until fully combined.

3. Layer the Cinnamon Sugar Filling Into the Dough:

• Layer the dough: Once the dough is ready, remove half of it from the mixing bowl and set it aside. Spread the remaining dough out across the bottom of the mixing bowl.
• Add the cinnamon filling: Remove the cinnamon sugar mixture from the freezer. Use two spoons to scoop small pieces of the cinnamon mixture (about a teaspoon each) and place them evenly over the dough.
• Top with more dough: Take the dough you set aside earlier and press it into an even layer on top of the cinnamon filling.
• Add the remaining cinnamon filling: Spoon the rest of the cinnamon-sugar mixture on top of the second layer of dough.

4. Mix the Dough Together:

• Fold gently: Use a rubber spatula to gently fold the dough together. You want to stir just enough to create a swirled effect without fully incorporating the cinnamon filling. Leave some chunks of the cinnamon mixture intact to create a marbled effect.

5. Chill the Dough:

• Freeze the dough: Scoop the dough into two-tablespoon portions using a cookie scoop. Place the dough balls on a plate and freeze them for 10 minutes. This quick chill firms up the butter, preventing the cookies from spreading too much during baking.

6. Bake the Cookies:

• Preheat and prep: Preheat your oven to 350°F. Line two baking sheets with parchment paper or silicone baking mats.
• Place dough on baking sheets: Arrange the chilled dough balls on the prepared baking sheets, spacing them a couple of inches apart. For thicker cookies, leave the dough in higher mounds; for thinner cookies, flatten them slightly with your fingers.
• Bake: Bake the cookies for 10-12 minutes until they have spread slightly, the edges are golden brown, and the centers are just set. Some cookies might be a bit misshapen, which is fine because of the cinnamon filling melting out, but don’t worry—we’ve got you covered on shaping them.

7. Shape the Cookies (Optional):

• Option 1 – Glass or Cookie Cutter Method: As soon as the cookies come out of the oven, place a round glass, bowl, or cookie cutter (larger than the cookie) upside down over the top of the cookie. Gently swirl the glass in a circular motion, and the edges of the cookie will form into a perfect round shape.
• Option 2 – Spoon Method: Alternatively, use the back of a spoon to gently push the edges inward to create clean, round shapes.

8. Cool and Enjoy:

• Cool on wire racks: Let the cookies cool on the baking sheets for a few minutes before transferring them to wire racks. The cookies will firm up as they cool, ensuring a chewy, soft texture in the center and a slightly crisp edge.

Helpful Tips and Variations:

• Flour Measurement: To properly measure flour, fluff it several times in its container, scoop it lightly into your measuring cup, and level it off with the back of a knife. This ensures you don’t use too much flour, which can make the cookies dry.
• Substitutions:
  • If you prefer a dairy-free version, use dairy-free butter and substitute the buttermilk with non-dairy milk (like almond or soy milk).
  • For a richer flavor, try adding a pinch of nutmeg or cloves to the cinnamon-sugar filling.
  • If you’re not a fan of cinnamon, you can use other spices like cardamom or ginger for a different twist.
• Storage: Store the cookies in an airtight container at room temperature for up to a week. You can also freeze the dough balls for later use. Simply scoop the dough, freeze it on a baking sheet, then transfer the dough balls to a Ziploc bag. Bake them directly from the freezer, adding a couple of extra minutes to the baking time.

Serving Suggestions:

These Cinnamon Roll Sugar Cookies are perfect for a variety of occasions:

• With coffee or tea: Serve them alongside your morning cup of coffee or tea for a comforting start to the day.
• For gatherings: They’re great for family gatherings, holidays, or cookie swaps. Their chewy texture and cinnamon flavor are sure to be a hit.
• Toppings: For extra indulgence, drizzle the cookies with a simple glaze or dust them with powdered sugar for a sweet finish.

Conclusion:

These Cinnamon Roll Sugar Cookies are everything you could want in a cookie—soft, chewy, and filled with a swirl of cinnamon and brown sugar that is pure magic. With just the right amount of sweetness and spice, they capture the essence of cinnamon rolls in a cookie form. Whether you’re baking for a special occasion or just want to treat yourself, this recipe will surely satisfy your cinnamon cravings and become a favorite in your baking rotation!