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Cinnamon roll cookies with a visible spiral and a thin vanilla glaze drizzle

Cinnamon Roll Cookies

Buttery slice-and-bake cookies with a defined cinnamon-sugar spiral, lightly crisp edges, soft centers, and a thin vanilla glaze drizzled over the top, baking up like a cross between a sugar cookie and a cinnamon roll. Rolling the dough into a log and chilling it firm before slicing is what keeps the spiral clean and distinct instead of smearing together under the knife, similar to the logic behind chilling stuffed cookie dough before baking. Pulling the tray while the centers still look just set leaves a slightly gooey, caramelized swirl rather than a dry one once the cookies have cooled.
Prep Time 35 minutes
Cook Time 15 minutes
Chill Time 1 hour 30 minutes
Total Time 2 hours 20 minutes
Servings: 12
Course: Baking, Cookies
Cuisine: American
Calories: 410

Ingredients
  

For the Cookie Dough
  • 340 g all-purpose flour
  • 1 tsp baking powder
  • ½ tsp fine salt
  • 225 g unsalted butter softened but still cool
  • 150 g granulated sugar
  • 1 large egg room temperature
  • 1 large egg yolk room temperature
  • 2 tsp vanilla extract
For the Cinnamon Filling
  • 60 g unsalted butter very soft
  • 120 g light brown sugar packed
  • 1½ tbsp ground cinnamon
  • 1 tbsp all-purpose flour
  • Pinch of fine salt
For the Vanilla Glaze
  • 120 g powdered sugar
  • 2–3 tbsp milk or heavy cream
  • ½ tsp vanilla extract
  • Tiny pinch of salt

Method
 

Make the Dough
  1. Whisk together the flour, baking powder, and salt in a medium bowl. In a large bowl, beat the softened butter and granulated sugar for 2 to 3 minutes, until smooth and slightly lighter, then beat in the egg, egg yolk, and vanilla until fully combined. Add the dry ingredients and mix just until a soft dough forms with no visible dry flour, stopping as soon as it comes together, since overmixing makes the cookies tougher and harder to roll neatly.
Rest the Dough
  1. Divide the dough into 2 equal portions, flatten each into a rough rectangle, wrap, and chill for 20 to 30 minutes. The dough should be cool and firmer but still pliable; too soft and the filling will smear, too cold and it may crack while rolling.
Prepare the Filling
  1. Mix the soft butter, brown sugar, cinnamon, flour, and salt in a small bowl into a spreadable paste. The flour here keeps the filling from melting out too aggressively during baking.
Roll and Fill
  1. Working with one dough portion at a time on a lightly floured surface, roll into a rectangle about 20 x 25 cm and 4 to 5 mm thick. Spread half of the cinnamon filling evenly over the surface, leaving a 1 cm border on one long edge, then roll the dough up tightly from the opposite long edge into a log and pinch the seam gently closed. Repeat with the second portion. Roll tightly to keep the spiral defined, avoid too much bench flour or the dough won't seal well, and chill briefly if the dough softens or the filling starts slipping while rolling.
Chill the Logs
  1. Wrap each log tightly in parchment or plastic wrap and chill for at least 1 hour, or until firm enough to slice cleanly. Rotating the logs once halfway through chilling keeps them from flattening on one side, for extra-clean spirals. Don't skip this chill; firm logs are what keep the cookies thick, the swirls clean, and the filling from leaking out.
Slice
  1. Heat the oven to 175°C / 350°F and line baking trays with parchment. Trim the ends if uneven, then slice each log into 12 cookies, about 1.5 cm thick, for 24 total. Gently round any slice that loses its shape with your fingers before placing it on the tray.
Bake
  1. Arrange the cookies with space between them, about 6 to 8 per tray, and bake for 12 to 14 minutes, until the edges are lightly golden, the centers are set but still look slightly soft, and the spiral lines look a little glossy and caramelized. Cool on the tray for 5 minutes before transferring to a rack. Don't overbake; these cookies continue to set as they cool, so pull them when the centers are just set for a thicker, slightly gooey swirl.
Glaze
  1. Whisk the powdered sugar, 2 tablespoons of milk or cream, vanilla, and salt until smooth, adding a little more liquid only if needed. The glaze should be fluid enough to drizzle but not so thin that it floods the spiral. Drizzle lightly over the cooled or just-warm cookies, keeping the spiral clearly visible underneath.

Notes

Chilling the logs until truly firm is the step that determines how clean the final spiral looks. Dough that's still soft when sliced tends to smear under the knife and blur the swirl instead of keeping it distinct.
A sharp knife matters more here than in most slice-and-bake cookies, since the sticky filling can drag through softer cuts. Wiping the blade clean every few slices keeps each cookie's spiral crisp.
The small amount of flour in the cinnamon filling is doing real work, holding the filling together enough that it caramelizes in place rather than melting out and pooling on the tray during baking.
Letting the cookies cool fully before glazing gives cleaner, more defined white drizzles. Glazing them while still warm melts the glaze into a thinner, more translucent finish that shows less contrast against the spiral.