The Memory Behind This Treat
The idea for these Cinnamon Roll Sugar Cookies came from one very loud family debate at my mom’s kitchen table. Half the crew wanted my classic soft sugar cookies; the other half was lobbying hard for gooey cinnamon rolls. I remember staring at the mixing bowl, butter already softening on the counter, and thinking, “Why are we choosing?” So instead of picking a side, I rolled my sugar cookie dough thin, sprinkled it with a brown sugar–cinnamon layer the way my grandma did for her Sunday rolls, and sliced it into spirals. When that first batch came out of the oven—golden at the edges, soft in the center, swirled like mini cinnamon buns—the table went quiet in the best possible way.
These Cinnamon Roll Sugar Cookies have become our in-between-season tradition, the kind of treat I make on days that feel like they can’t decide between cozy and celebratory. I’ll pull the dough together while coffee brews, roll it up into a tidy log, and tuck it into the fridge while I clear the counters or prep something savory, the way I might if I were making yeast rolls. Where classic cinnamon rolls demand a whole morning and a lot of patience, these give you the same warm vanilla-cinnamon aroma with far less commitment. They remind me that you don’t always need a special occasion or a perfect block of time to make something that feels a little magical. Sometimes you just need softened butter, a sprinkle of cinnamon, and the permission to break a baking “rule” or two.
How To Make It (Mix & Ingredients)
To make these Cinnamon Roll Sugar Cookies, you’ll start with a classic soft sugar cookie dough and then give it that cozy cinnamon-roll twist. Whisk together your dry ingredients first: all-purpose flour, baking powder, and salt. This keeps the leavening evenly distributed and prevents surprise salty pockets later. In a separate large bowl, cream softened unsalted butter with granulated sugar until it looks pale and fluffy—this usually takes 2–3 minutes with an electric mixer and is what gives your cookies that soft, tender crumb. Beat in the egg and vanilla bean paste until the mixture looks smooth and a little satiny; if it looks curdled, just keep mixing for another 20–30 seconds.
Instructions Process of Cinnamon Roll Sugar Cookies
Once your wet ingredients are ready, gently add the dry mixture in on low speed, just until a soft dough forms. It should pull away from the sides of the bowl but still feel a bit tacky—kind of like Play-Doh that sat out for a few minutes. If it’s sticking aggressively to your hands, you can sprinkle in 1–2 extra tablespoons of flour, but don’t overdo it or you’ll lose that lovely chew. For the “cinnamon roll” swirl, stir together the brown sugar and ground cinnamon in a small bowl; use a fork to break up any clumps so it sprinkles evenly. Roll your dough into a rectangle about 1/4 inch thick, then shower it with the cinnamon sugar, reaching all the way to the edges for maximum swirl in every bite. Roll it up tightly from the long side into a log, chill it until firm, then slice, bake, and finish with a quick icing made from confectioners’ sugar, milk, and a little more vanilla bean paste.
Make-Ahead & Storage
Cinnamon Roll Sugar Cookies are wonderfully make-ahead friendly, which makes them perfect for busy holidays and parties. For the best flavor and texture, I recommend making the dough log in advance rather than baking too far ahead. Once you’ve rolled the dough into a cinnamon swirl log, wrap it tightly in plastic, then in foil, and chill for up to 3 days. When you’re ready to bake, simply slice and bake straight from the fridge, adding 1–2 extra minutes in the oven if the slices are very cold. This method gives you fresh, soft and chewy cookies on your timeline, without redoing all the prep.
If you want to plan even farther ahead, you can freeze the unbaked dough log for up to 2 months. Freeze it on a baking sheet until solid, then wrap well (plastic + foil or a freezer bag) to prevent freezer smells from sneaking in. When you’re craving Cinnamon Roll Sugar Cookies, let the log sit at room temperature for about 15–20 minutes so it’s easier to slice, then bake as directed. Baked cookies also freeze nicely: place cooled cookies (without icing, for best texture) in a single layer to freeze, then transfer to an airtight container with parchment between layers. Thaw at room temperature and drizzle with fresh icing right before serving for that just-baked look and taste.
On the counter, store fully cooled, iced cookies in an airtight container at room temperature for 3–4 days. I like to line the container with parchment and add a small sheet between layers so the icing doesn’t smudge. If your kitchen runs warm or humid, you can refrigerate them instead, but let the cookies sit out for 10–15 minutes before serving so the centers soften back to that perfect chewy texture.
Best Ingredients & Party Variations
For the softest, chewiest Cinnamon Roll Sugar Cookies, start with high-fat unsalted butter and room-temperature ingredients. Good butter gives you that rich bakery-style flavor and helps the cookies stay tender instead of dry. Use fresh ground cinnamon (if it’s been in your cabinet longer than 1–2 years, it’s time to replace it) for a bold swirl that actually tastes like a real cinnamon roll. I love vanilla bean paste here because you get those pretty specks and a deeper flavor, but pure vanilla extract works if that’s what you have. Stick with standard all-purpose flour, spooned and leveled, so the dough rolls easily without cracking.
Once you’ve got your base, these Cinnamon Roll Sugar Cookies are made for parties. For a brunch spread, drizzle the cookies with a slightly thicker icing and top each one with a tiny pinch of coarse sugar or chopped pecans so they feel a bit fancy next to your coffee cake and muffins. For kids’ birthdays, tint part of the icing a pale pink or caramel color and zigzag it over the cookies, then add a few sprinkles while it’s still wet. You can even slice the dough a bit smaller to make “mini” cinnamon roll cookies that are perfect for dessert boards alongside chocolate chunk cookies or snickerdoodles. Around the holidays, add a pinch of nutmeg to the cinnamon sugar filling and a splash of maple in the icing to turn these into cozy, giftable cookie-tin stars.
Serving of Cinnamon Roll Sugar Cookies
Conclusion
If you’re anything like me, you’re already picturing a plate of these still-warm cookies on your kitchen counter, a little swirl of icing glistening on top, and someone you love reaching for “just one more.” That’s the quiet magic of baking—simple ingredients turning into little invitations to slow down, sit together, and share a moment. These Soft and Chewy Cinnamon Roll Sugar Cookies are the kind of cookie that makes an ordinary afternoon feel a bit more like a celebration.
I hope you give this recipe a spot in your own home baking traditions—maybe for a cozy Sunday, a holiday cookie tray, or a midweek pick-me-up. Don’t overthink it, just preheat the oven, turn on some music, and let your kitchen smell like a bakery. You might be surprised how quickly people wander in when they catch that warm cinnamon scent.
When you bake them, I’d love for you to share your batch and tag us—seeing your creations truly makes my day.
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What keeps these Cinnamon Roll Sugar Cookies so soft and chewy?
The creamed butter and sugar create tiny air pockets that keep the dough tender, while the single egg adds moisture without making the cookies cakey. Using the full amount of flour, but not packing it into the cup too tightly, helps you avoid dry, tough cookies. Rolling the dough to about 1/4 inch gives just the right thickness for a soft center and lightly set edges. For the best texture, pull the cookies from the oven when the edges barely start to turn golden and the centers still look slightly pale. They’ll continue to set on the baking sheet as they cool, staying soft and chewy instead of crisp.
How can I keep the cinnamon swirl neat and prevent the dough from sticking?
Lightly flour your counter, rolling pin, and hands, but don’t go overboard or you’ll dry out the dough. If the dough feels soft or sticky, pop it in the fridge for 20–30 minutes before rolling so it firms up slightly. When you add the cinnamon sugar, leave a small border along the edge so it doesn’t all spill out when you roll. Roll the dough snugly, but not too tight, starting from the long side to get more spirals in each cookie. Use a sharp knife or serrated knife to slice the chilled log, wiping the blade clean every few cuts for sharp, defined swirls.
Recipe
Soft and Chewy Cinnamon Roll Sugar Cookies
Ingredients
Ingredients
- 2 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/2 teaspoon salt
- 1 cup unsalted butter softened
- 1 cup granulated sugar
- 1 large egg
- 1 1/2 teaspoons vanilla bean paste divided
- 1/2 cup packed brown sugar
- 2 tablespoons ground cinnamon
- 1 cup confectioners' sugar
- 2 tablespoons milk
Instructions
- Preheat the oven to 350°F. Line two baking sheets with parchment paper and set aside.
- In a medium bowl, whisk together the flour, baking powder, and salt until well combined; set aside.
- In a large mixing bowl, beat the softened butter and granulated sugar with an electric mixer on medium speed until light and fluffy, about 2 to 3 minutes.
- Add the egg and 1 teaspoon of the vanilla bean paste to the butter mixture and beat until smooth and fully combined.
- Add the dry ingredients to the wet ingredients in 2 to 3 additions, mixing on low speed just until a soft dough forms and no dry flour remains.
- In a small bowl, stir together the brown sugar and ground cinnamon until evenly combined and free of lumps to make the filling.
- Lightly flour a clean work surface and roll the cookie dough into a rectangle about 1/4 inch thick.
- Sprinkle the cinnamon-brown sugar mixture evenly over the rolled-out dough, reaching all the way to the edges.
- Starting from one long edge, tightly roll the dough into a log to create a spiral, pinching the seam gently to seal.
- Transfer the dough log to a baking sheet or plate, cover lightly, and refrigerate for at least 30 minutes until firm enough to slice.
- Once chilled, use a sharp knife to slice the log into 1/4-inch-thick rounds and arrange them on the prepared baking sheets, spacing about 2 inches apart.
- Bake for 10 to 12 minutes, or until the edges are just starting to turn light golden and the centers look set.
- Allow the cookies to cool on the baking sheets for 3 to 5 minutes, then transfer them to a wire rack to cool completely.
- While the cookies cool, whisk together the confectioners' sugar, milk, and remaining 1/2 teaspoon vanilla bean paste in a small bowl until smooth and pourable.
- Drizzle the vanilla icing over the cooled cookies, let the icing set for several minutes, then serve or store.
Notes
- For neater drizzles, transfer the icing to a small piping bag or a zip-top bag with a tiny corner snipped off.