Cinnamon Roll Cookies with Brown Sugar Swirls

Cinnamon Roll Cookies

These cinnamon roll cookies are sliced pinwheels with brown-sugar-cinnamon spirals, lightly golden edges, and thin white icing. The filled dough is rolled into two logs, then chilled until firm enough to cut without flattening. That chill helps the spirals stay visible as the cookies bake.

Plan on about 35 minutes of preparation, 2 hours of chilling, and 10 to 12 minutes of baking per sheet. Including cooling and glazing, the total time is about 3 hours 15 minutes to 3 hours 45 minutes.

Ingredients for Cinnamon Roll Cookies

Cookie dough

• 3/4 cup unsalted butter, softened (170g)
• 3/4 cup granulated sugar (150g)
• 1 large egg
• 1 teaspoon vanilla extract
• 2 1/4 cups all-purpose flour (270g)
• 1/2 teaspoon baking powder
• 1/2 teaspoon fine salt

Cinnamon filling

• 2 tablespoons unsalted butter, softened (about 30g)
• 1/3 cup packed light brown sugar (about 65g)
• 1 tablespoon ground cinnamon

White icing

• 3/4 cup powdered sugar (90g)
• 1 to 2 tablespoons milk

How to Make Cinnamon Roll Cookies

1. Mix the dough: Beat the 3/4 cup softened butter and granulated sugar until creamy. Mix in the egg and vanilla. Add the flour, baking powder, and salt, mixing just until no dry flour remains and the dough holds together.
2. Make the filling: Mix the 2 tablespoons softened butter, brown sugar, and cinnamon until spreadable.
3. Roll and fill: Divide the dough in half. On parchment, roll each portion into an approximately 8-by-12-inch rectangle, about 1/4 inch thick. If the dough sticks, refrigerate it briefly before continuing. Spread half the filling thinly over each rectangle, leaving a clean 1/2-inch border along one long edge.
4. Form and chill the logs: Starting at the opposite long edge, roll each rectangle snugly toward the clean border without squeezing out the filling. Press the clean edge against the log to seal it. Wrap the logs and refrigerate for about 2 hours, until firm throughout. A test slice should hold its round shape rather than flatten.
5. Slice and bake: As the logs finish chilling, position a rack near the center of the oven and preheat to 350°F (175°C). Line baking sheets with parchment. Cut the logs into approximately 1/2-inch slices with a sharp knife, using gentle strokes. Place the slices about 2 inches apart; refrigerate any that soften or squash as you work. Bake uncovered, one sheet at a time, for 10 to 12 minutes. Start checking at 10 minutes and remove the cookies when the edges are set and lightly golden and the centers look set but still tender.
6. Cool and ice: Leave the cookies on the baking sheet for 5 minutes, then transfer them to a rack to cool completely. Stir the powdered sugar with 1 tablespoon milk, adding more a little at a time until the icing falls in thin, opaque ribbons. Drizzle over the cooled cookies and let the icing set before stacking.

How to Keep the Cinnamon Spirals Defined

A thin filling layer and clean sealing border help keep the cinnamon sugar inside the logs. Slice only when the logs are firm enough that the knife does not press them oval. If a log is too hard to cut, let it soften slightly, then slice it before it becomes floppy. A few less-complete spirals, particularly near the ends, are normal.

How to Tell When the Cookies Are Done

Look for lightly golden, set edges and centers that no longer look raw. The cookies firm up as they cool, so do not wait for deep browning across the tops. Wider or thicker slices may need more than 12 minutes; use their appearance rather than the clock alone.

Make-Ahead and Storage

Wrapped, filled logs can be refrigerated until ready to slice. For longer storage, wrap them well and freeze for up to 3 months. Let frozen logs soften just enough to cut cleanly.

Once the icing has set, store the cookies airtight at room temperature for up to 4 days, with parchment between stacked layers. Baked cookies can also be frozen for up to 3 months; for the clearest white drizzle, glaze them after thawing. Serve with coffee, tea, or hot chocolate.

For another warmly spiced cookie, try these soft and chewy oatmeal raisin cookies. For a chocolate option, try these chocolate chunk cookies.

Nutrition

Estimated per 1/24 of the recipe: 155 calories, 2g protein, 7g fat, and 22g carbohydrates. Estimated per 100g of finished cookies: 455 calories, 4g protein, 20g fat, and 64g carbohydrates. These are approximations; the number and weight of cookies will vary with the size of the logs and slices.