These soft and chewy cinnamon roll sugar cookies transform the beloved flavor of classic cinnamon rolls into a convenient cookie form. Each bite delivers the perfect balance of buttery cookie base with warm cinnamon swirls, all topped with a sweet vanilla glaze that hardens just enough to make these cookies perfectly stackable and giftable.

Name: Soft and Chewy Cinnamon Roll Sugar Cookies
Prep time: 20 min
Cook time: 10 min
Total time: 1 h 30 min
Cuisine: American
Ingredients: 2 1/2 cups all-purpose flour; 1/2 teaspoon baking powder; 1/2 teaspoon salt; 3/4 cup unsalted butter, softened; 1 cup granulated sugar; 1 large egg; 2 teaspoons vanilla extract; For the cinnamon filling:; 1/4 cup unsalted butter, melted; 1/3 cup brown sugar, packed; 1 1/2 teaspoons ground cinnamon; For the glaze:; 1 cup powdered sugar; 2–3 tablespoons milk; 1/2 teaspoon vanilla extract

Why You’ll Love This Recipe

These cinnamon roll sugar cookies combine two beloved treats into one irresistible package. The soft, chewy texture provides the perfect canvas for the warm cinnamon filling that swirls throughout. The vanilla glaze adds just the right touch of sweetness that will remind you of a freshly baked cinnamon roll, but in a convenient, handheld cookie form. They’re impressive enough for special occasions but simple enough for weekend baking projects. Perfect for holiday cookie exchanges, afternoon tea, or whenever you’re craving something special without the time commitment of traditional cinnamon rolls.

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

All-purpose flour creates the foundation for these cookies, providing structure while still allowing for a tender bite. The protein content in all-purpose flour is perfect for achieving that soft yet chewy texture we’re looking for.

Baking powder gives these cookies just enough lift without making them cakey. It’s the secret to maintaining that perfect cookie texture while still resembling a cinnamon roll.

Salt balances the sweetness and enhances all the flavors in these cookies. Don’t skip it, as even this small amount makes a significant difference in the final taste.

Unsalted butter brings richness and that melt-in-your-mouth quality to both the cookie dough and the filling. Make sure it’s properly softened for the dough so it creams correctly with the sugar.

Granulated sugar sweetens the cookie dough and helps create those slightly crisp edges while maintaining a soft center. It also helps the cookies spread properly during baking.

Brown sugar adds a deeper, more complex sweetness to the filling thanks to its molasses content. It also contributes to the classic cinnamon roll flavor and helps create that gooey texture in the swirl.

Eggs bind the ingredients together and add moisture to the dough. They also contribute to the chewiness of the finished cookie.

Vanilla extract enhances all the other flavors in both the cookie and the glaze. Its warm, aromatic quality pairs beautifully with cinnamon.

Ground cinnamon is the star of the filling, providing that warm, spicy flavor that defines a great cinnamon roll. Use fresh cinnamon for the best flavor intensity.

Powdered sugar creates a smooth, sweet glaze that hardens just enough to set but remains slightly soft to the bite. Its fine texture ensures a lump-free topping.

Milk thins the glaze to the perfect consistency for drizzling. You can adjust the amount to make the glaze thicker or thinner according to your preference.

Directions

In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
In a large mixing bowl, cream the softened butter and granulated sugar together until light and fluffy.
Beat in the egg and vanilla extract until well combined.
Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
Divide the dough into two portions, flatten into discs, and wrap in plastic wrap. Chill for at least 1 hour.
Preheat the oven to 350°F (175°C) and line baking sheets with parchment paper.
Roll out one portion of the chilled dough into a rectangle about 1/4 inch thick.
Brush the surface with melted butter, sprinkle evenly with brown sugar and cinnamon.
Starting from the longer side, roll up the dough tightly into a log. Repeat with the second portion.
Slice each log into 1/2-inch thick rounds and place them on prepared baking sheets.
Bake for 9–11 minutes, or until the edges are just beginning to turn golden.
Let the cookies cool on the baking sheets for 5 minutes before transferring to a wire rack.
For the glaze, whisk together powdered sugar, milk, and vanilla extract until smooth. Drizzle over the cooled cookies.

Servings and Timing

This recipe makes approximately 24 cookies, depending on how thick you slice your cookie dough logs. Each cookie contains about 165 calories.

Prep Time: 20 minutes (plus 1 hour for chilling)
Cooking Time: 10 minutes
Total Time: 1 hour 30 minutes

Variations

Cardamom Twist: Add 1/2 teaspoon of ground cardamom to the filling for a Scandinavian-inspired flavor profile.
Orange Glaze: Add 1 teaspoon of orange zest to the glaze and substitute orange juice for the milk for a bright, citrusy finish.
Nutty Crunch: Sprinkle finely chopped pecans or walnuts over the cinnamon-sugar filling before rolling for added texture and flavor.
Chocolate Chip: Sprinkle mini chocolate chips over the cinnamon filling for a chocolate-cinnamon combo.
Maple Glaze: Replace the vanilla in the glaze with maple extract and add a tablespoon of real maple syrup for a fall-inspired treat.
Cream Cheese Filling: Mix 2 ounces of softened cream cheese with the brown sugar and cinnamon for a tangy filling reminiscent of cream cheese frosted cinnamon rolls.

Storage/Reheating

Counter Storage: Store cooled cookies in an airtight container at room temperature for up to 3-4 days. Place parchment paper between layers to prevent sticking, especially if they’re glazed.

Refrigerator Storage: These cookies can be stored in the refrigerator for up to a week. Allow them to come to room temperature before serving for the best texture and flavor.

Freezer Storage: Unglazed cookies freeze beautifully for up to 3 months. Place them in a single layer on a baking sheet until frozen solid, then transfer to a freezer-safe container with parchment paper between layers. Thaw at room temperature and add the glaze before serving.

Dough Storage: The prepared dough logs can be wrapped tightly in plastic wrap and refrigerated for up to 3 days before slicing and baking. You can also freeze the logs for up to a month – thaw overnight in the refrigerator before slicing and baking.

Reheating: To refresh slightly stale cookies, warm them in the microwave for 8-10 seconds. This will soften them and enhance their cinnamon aroma. If frozen, allow cookies to thaw completely at room temperature before enjoying or gently warm in a 300°F oven for 3-4 minutes.

FAQs

Why did my cookies spread too much during baking?

Excessive spreading usually occurs when the butter is too soft or the dough wasn’t chilled long enough. Make sure to chill the dough for at least one hour. If your kitchen is particularly warm, you might need to chill the sliced cookies again for 10-15 minutes before baking.

Can I make these cookies ahead of time?

Absolutely! You can prepare the dough logs and refrigerate them for up to 3 days or freeze for up to a month. You can also bake the cookies and freeze them unglazed, then add fresh glaze after thawing.

My cinnamon filling leaked out during baking. What went wrong?

This can happen if the filling is spread too close to the edges of the dough rectangle. Leave about a 1/2-inch border around the edges when applying the filling, and make sure to roll the dough tightly. Also, ensure your dough is properly chilled and firm before slicing.

Can I use salted butter instead of unsalted?

Yes, you can use salted butter, but reduce or omit the added salt in the recipe. Keep in mind that different brands of salted butter contain varying amounts of salt, so the flavor may differ slightly.

How do I know when the cookies are done baking?

These cookies should be removed from the oven when the edges are just beginning to turn golden, but the centers still look slightly underbaked. They will continue to cook on the hot baking sheet after removal from the oven. Overbaking will result in harder, crisper cookies rather than soft and chewy ones.

Can I use a stand mixer for this recipe?

Absolutely! A stand mixer with the paddle attachment works perfectly for creaming the butter and sugar and mixing in the dry ingredients. Just be careful not to overmix once the flour is added.

My glaze is too thick/thin. How do I fix it?

For thick glaze, add more milk, 1/2 teaspoon at a time. For thin glaze, add more powdered sugar, 1 tablespoon at a time, until you reach your desired consistency.

Can I double this recipe?

Yes, this recipe doubles well. Just make sure you have enough refrigerator space for chilling the dough and enough counter space for rolling it out.

Why do I need to chill the dough?

Chilling the dough firms up the butter, which prevents excessive spreading during baking. It also makes the dough easier to handle when rolling and shaping. Don’t skip this step!

Can I make these cookies gluten-free?

Yes, you can substitute a 1-to-1 gluten-free flour blend in place of the all-purpose flour. The texture may be slightly different, but they should still be delicious.

Conclusion

These Soft and Chewy Cinnamon Roll Sugar Cookies perfectly capture the cozy, comforting flavors of traditional cinnamon rolls in a convenient cookie form. The balance of the buttery, soft cookie base with the warm, spiced cinnamon swirl creates a treat that’s perfect for any occasion, from holiday cookie exchanges to afternoon coffee breaks.

What makes these cookies special is not just their delicious flavor, but their visual appeal – each cookie showcases a beautiful spiral pattern that will impress family and friends alike. The versatility of this recipe also means you can adapt it to different seasons and preferences with the suggested variations.

Whether you’re an experienced baker or just starting out, these cinnamon roll sugar cookies are bound to become a favorite in your recipe collection. They offer all the satisfaction of homemade cinnamon rolls with a fraction of the time and effort, proving that sometimes the best treats come in smaller packages.