These cookies take everything you love about a cinnamon roll and shrink it down into a simple sugar cookie base. A sweet, cinnamon-sugar filling gets rolled up inside the dough, sliced, baked, and finished with a sweet icing drizzle, giving you that classic swirl look in every bite.
Quick facts
- Prep time: 2 hours 20 minutes (includes chilling)
- Cook time: 10 minutes
- Total time: 2 hours 40 minutes
- Makes: about 36 cookies
Ingredients
For the dough
- 2 and 1/4 cups (281g) all-purpose flour (spooned & leveled), plus more as needed for rolling and work surface
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
- 3/4 cup (12 Tbsp; 170g) unsalted butter, softened to room temperature
- 3/4 cup (150g) granulated sugar
- 1 large egg, at room temperature
- 2 teaspoons pure vanilla extract
For the filling
- 2 Tablespoons (28g) butter, melted and slightly cooled
- 1/4 cup (50g) granulated sugar
- 1 Tablespoon ground cinnamon
For the icing
- 1 cup (120g) confectioners’ sugar
- 3 Tablespoons (45ml) milk
- 1/2 teaspoon pure vanilla extract
How to Make Cinnamon Roll Cookies
Part 1: Make the Dough
1. Mix the dry ingredients. In a medium bowl, whisk together the flour, baking powder, and salt. Set this aside.
2. Cream the butter and sugar. In a large bowl, using a handheld or stand mixer, beat the butter and sugar together on high speed until completely smooth and creamy, about 2 minutes.
3. Add the egg and vanilla. Beat these in on high speed until combined, about 1 minute, scraping down the bowl as needed.
4. Combine. Add the dry ingredients to the wet mixture and mix on low speed until combined. The dough will be a bit soft. If it feels too soft or sticky to roll, add an extra tablespoon of flour.
Part 2: Shape and Fill
5. Divide the dough. Split the dough into two equal portions.
6. Roll out the dough. On a floured silicone baking mat or floured parchment paper, roll each portion into a rectangle, about 9×7 inches, to roughly ¼ inch thick.
7. Add the filling. Spread 1 tablespoon of melted butter over each rectangle. Mix the sugar and cinnamon together, then sprinkle it evenly over both.
8. Roll into logs. Working slowly, tightly roll each rectangle into a 9-inch log. If the dough cracks a little, smooth it out with your fingers. A few small cracks are fine.
9. Chill. Chill the dough logs for at least 2 hours, or freeze for up to 3 months. Carefully transfer the logs to a cutting board or plate and cover loosely with plastic wrap while they chill.
Part 3: Slice and Bake
10. Preheat and prep. Heat the oven to 350°F (177°C) and line a large baking sheet with parchment paper or a silicone baking mat.
11. Slice the logs. Remove the chilled dough from the refrigerator and cut it into ½ inch slices.
12. Arrange on the sheet. Place the slices about 2 inches apart on the prepared baking sheet.
13. Bake. Bake for 10 to 11 minutes, until lightly browned on the sides.
14. Cool. Let the cookies cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely before icing.
Part 4: Ice the Cookies
15. Make the icing. Whisk together the confectioners’ sugar, milk, and vanilla until smooth.
16. Drizzle. Drizzle the icing over the cooled cookies.
Tips for the Best Cinnamon Roll Cookies
Add extra flour if the dough feels too sticky. A tablespoon or two makes a big difference in how easily the dough rolls out.
Roll the dough evenly. Keeping a consistent ¼ inch thickness helps the filling spread evenly and makes for uniform slices later.
Roll the log tightly. A tight roll gives you a more defined spiral once the cookies are sliced and baked.
Don’t skip the chilling time. Cold dough slices much more cleanly than dough fresh off the counter, and it also helps the cookies hold their shape in the oven.
Let the cookies cool completely before icing. Warm cookies will cause the icing to melt and run instead of setting nicely on top.
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Final Thoughts
These cinnamon roll cookies bring the best parts of a cinnamon roll into an easy, shareable cookie form. The spiral look makes them feel special, but the method is really just rolling, filling, slicing, and baking. Make a batch and let me know how yours turn out.