If you’re on the hunt for a dessert that effortlessly blends the warm, comforting aroma of cinnamon rolls with the beloved texture of classic sugar cookies, look no further. This Indulgent Cinnamon Roll Sugar Cookies With Chewy Perfection Recipe delivers the dreamiest, chewiest bite that feels like a cozy hug in cookie form. Each bite bursts with buttery sweetness and a swirl of cinnamon-sugar magic, perfect for sharing with friends or savoring all to yourself.

Ingredients You’ll Need
The beauty of this recipe lies in its straightforward, pantry-friendly ingredients that work harmoniously to create that flawless chew and irresistible flavor. Every component plays a starring role, from the creamy butter that forms the base to the fragrant cinnamon spice that brings those cinnamon roll vibes alive.
- ½ cup Unsalted Butter, softened: Adds a rich, creamy flavor essential for both the cookie dough and filling.
- 1¼ cups Granulated Sugar: Sweetens the dough while helping achieve a light, tender texture.
- ⅓ cup Brown Sugar, packed: Provides a deeper, molasses-like sweetness that enhances chewiness.
- 1 large Egg: Acts as a binder to hold the cookie dough together perfectly.
- 1 tsp Pure Vanilla Extract: Imparts a fragrant warmth that complements the cinnamon beautifully.
- 2¾ cups All-Purpose Flour: Gives structure to the cookies without weighing them down.
- ¾ tsp Baking Powder: Helps the cookies rise just the right amount for soft, chewy texture.
- ¼ tsp Salt: Balances sweetness and brings out the other flavors.
- 1 tsp Cornstarch: Adds tenderness, ensuring the cookies stay soft instead of cakey.
- 4 tbsp Unsalted Butter, softened (for filling): Creates a buttery, luscious base for the cinnamon-sugar swirl.
- ⅓ cup Brown Sugar, packed (for filling): Amplifies the sweetness inside each cookie.
- 2½ tsp Ground Cinnamon: Adds the iconic cinnamon flavor that makes this recipe a standout.
- 1½ tbsp All-Purpose Flour (for filling): Binds the filling ingredients, preventing oozing during baking.
- Pinch Salt (for filling): Enhances both sweetness and richness in the cinnamon swirl.
How to Make Indulgent Cinnamon Roll Sugar Cookies With Chewy Perfection Recipe
Step 1: Prepare the Cookie Dough
Start by creaming together the ½ cup of softened unsalted butter with the granulated sugar and ⅓ cup brown sugar until light and fluffy. This process is crucial because it incorporates air into the dough, which helps achieve that perfect chewiness. Then, beat in the egg and vanilla extract until combined.
Step 2: Mix Dry Ingredients
In a separate bowl, whisk together the all-purpose flour, baking powder, salt, and cornstarch. Gradually add these dry ingredients to the wet mixture, mixing gently until everything is just combined — be careful not to over-mix, as that could toughen the cookies.
Step 3: Prepare the Cinnamon Roll Filling
Mix together the softened butter, brown sugar, cinnamon, flour, and pinch of salt in a small bowl until it forms a thick, spreadable paste. This mixture is where that signature cinnamon roll swirl flavor shines, infusing each cookie with irresistible warmth.
Step 4: Assemble the Cookies
Divide the cookie dough into small balls about the size of a tablespoon. Flatten each ball into a disc, then spread a thin layer of the cinnamon roll filling on top. Roll up the dough carefully or fold it to encapsulate the filling, ensuring the cinnamon swirl stays nestled inside.
Step 5: Bake to Chewy Perfection
Place the cookies on a parchment-lined baking sheet, spaced evenly. Bake in a preheated oven at 350°F (175°C) for about 12 minutes, or until the edges are set but the centers still look slightly soft. This ensures the cookies come out with that coveted chewy texture and melting softness.
How to Serve Indulgent Cinnamon Roll Sugar Cookies With Chewy Perfection Recipe

Garnishes
For an extra touch of indulgence, a light glaze made of powdered sugar and vanilla or a drizzle of cream cheese frosting complements these cookies beautifully. Sprinkling a little extra cinnamon or even some chopped pecans can add a bit of texture and visual appeal.
Side Dishes
These cookies pair wonderfully with a warm cup of spiced chai tea, a frothy cappuccino, or even a cold glass of milk. Their sweet and aromatic profile balances perfectly with both hot and cold beverages, making every bite a cozy experience.
Creative Ways to Present
Try stacking these cinnamon roll sugar cookies on a festive platter dusted with cinnamon sugar for a charming dessert table addition. You can also sandwich them with cream cheese filling for a twist or serve warm alongside vanilla ice cream for an unforgettable treat.
Make Ahead and Storage
Storing Leftovers
Store any leftover cookies in an airtight container at room temperature for up to five days. They actually mellow and become even chewier after a day, so wait if you can resist!
Freezing
You can freeze these cookies either before baking by shaping and placing them on a tray, then transferring to a freezer bag, or freeze fully baked cookies. This recipe freezes beautifully and can be kept frozen for up to three months.
Reheating
To revive that fresh-baked warmth, let frozen cookies thaw at room temperature and then reheat in the oven at 300°F (150°C) for about 5 minutes. This brings back that chewy softness and aroma that makes the Indulgent Cinnamon Roll Sugar Cookies With Chewy Perfection Recipe so irresistible.
FAQs
Can I use margarine instead of butter?
While margarine can be used, it won’t deliver quite the same rich, creamy flavor or texture that unsalted butter provides, which is key for this Indulgent Cinnamon Roll Sugar Cookies With Chewy Perfection Recipe.
How do I keep the cookies chewy instead of crunchy?
Using brown sugar and cornstarch as specified in the recipe helps maintain softness and chewiness. Also, be careful not to overbake; removing the cookies when the centers still look soft is essential.
Can I make these gluten-free?
Yes, you can substitute the all-purpose flour with a 1-to-1 gluten-free baking flour blend. Just ensure the blend contains xanthan gum or another binder to keep the cookies from crumbling.
Do the cookies need to be refrigerated before baking?
For this recipe, chilling the dough is not required, but if you prefer working with less sticky dough, a brief 20-30 minute chill can help.
What is the best way to store these cookies for gifting?
Layer the cookies between sheets of parchment or wax paper inside a sturdy tin or airtight box to keep them from sticking or breaking during transport. Including a little sachet of cinnamon can add a delightful aroma inside the package!
Final Thoughts
This Indulgent Cinnamon Roll Sugar Cookies With Chewy Perfection Recipe is a true labor of love that rewards you with extraordinary flavor and texture. Whether you’re baking for a crowd or treating yourself, these cookies bring a sense of joy and warmth that’s impossible to resist. I cannot wait for you to give this recipe a try and make it a treasured staple in your cookie collection!
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Indulgent Cinnamon Roll Sugar Cookies With Chewy Perfection Recipe
- Prep Time: 20 minutes
- Cook Time: 12 minutes
- Total Time: 32 minutes
- Yield: 24 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Indulgent Cinnamon Roll Sugar Cookies combine the soft, chewy texture of sugar cookies with a delicious cinnamon roll-inspired filling. Perfect for those who love a sweet treat with a hint of cinnamon spice, these cookies offer rich buttery dough swirled with a warm cinnamon-sugar center, delivering cozy flavors in every bite.
Ingredients
Cookie Dough
- ½ cup Unsalted Butter, softened (Adds a rich, creamy flavor)
- 1¼ cups Granulated Sugar (Sweetens the dough)
- ⅓ cup Brown Sugar, packed (Provides a deeper sweetness)
- 1 large Egg (Binds the ingredients)
- 1 tsp Pure Vanilla Extract (Imparts a fragrant flavor)
- 2¾ cups All-Purpose Flour (Gives structure to the cookies)
- ¾ tsp Baking Powder (Helps cookies rise)
- ¼ tsp Salt (Balances sweetness)
- 1 tsp Cornstarch (Adds tenderness to the cookies)
Cinnamon Filling
- 4 tbsp Unsalted Butter, softened (Creates a rich base for filling)
- ⅓ cup Brown Sugar, packed (Amplifies sweetness)
- 2½ tsp Ground Cinnamon (Adds classic cinnamon flavor)
- 1½ tbsp All-Purpose Flour (Binds filling ingredients)
- pinch Salt (Enhances sweetness and richness)
Instructions
- Prepare the Dough: In a large mixing bowl, cream together the ½ cup softened unsalted butter, granulated sugar, and ⅓ cup brown sugar until light and fluffy. Beat in the egg and vanilla extract until well combined. In a separate bowl, whisk together 2¾ cups flour, baking powder, salt, and cornstarch. Gradually incorporate the dry ingredients into the wet mixture, mixing until a smooth dough forms. Wrap the dough in plastic wrap and refrigerate for at least 30 minutes to firm up.
- Make the Cinnamon Filling: In a small bowl, blend the 4 tablespoons softened unsalted butter with ⅓ cup packed brown sugar, ground cinnamon, 1½ tablespoons flour, and a pinch of salt until the mixture forms a thick, spreadable paste.
- Assemble the Cookies: On a lightly floured surface, roll the chilled dough into a rectangle approximately ¼ inch thick. Evenly spread the cinnamon filling over the dough, leaving a small border around the edges. Carefully roll the dough into a tight log, starting from a long edge. Wrap the log in plastic wrap and chill for 15 minutes to firm.
- Slice and Bake: Preheat the oven to 350°F (175°C). Remove the dough log from the refrigerator and slice into 24 equal pieces, about ½ inch thick each. Place the slices cut-side down on a parchment-lined baking sheet, spacing them about 2 inches apart. Bake for 12 minutes or until the edges are lightly golden but centers remain soft.
- Cool and Serve: Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely. Serve immediately or store in an airtight container for up to 5 days.
Notes
- Make sure to chill the dough and cinnamon log to make slicing easier and prevent spreading while baking.
- For a richer taste, you can add a simple glaze of powdered sugar and milk drizzled over cooled cookies.
- These cookies keep well in an airtight container at room temperature for up to 5 days.
- You can substitute half the all-purpose flour with whole wheat flour for a nuttier flavor, but the texture may be slightly denser.

