Soft Cinnamon Roll Cookies with Vanilla Icing Drizzle

Why You’ll Love This Recipe

• All the cozy flavor of classic cinnamon rolls, but in an easy slice-and-bake cookie form.
• Soft, tender cookie dough wrapped around a buttery cinnamon-brown sugar swirl.
• A simple vanilla icing drizzle that looks bakery-style but takes minutes to mix.
• Perfect for holidays, cookie swaps, or anytime you want something comforting and impressive.

Grocery List

• Produce: 1 orange (optional, for zest in icing)
• Dairy: Unsalted butter, 1 large egg, milk or heavy cream
• Pantry: All-purpose flour, baking powder, granulated sugar, light brown sugar, powdered sugar, ground cinnamon, vanilla extract, fine salt

Full Ingredients

For the Cinnamon Roll Cookie Dough

• 2 1/2 cups (300 g) all-purpose flour
• 1/2 teaspoon baking powder
• 1/2 teaspoon fine sea salt (or table salt)
• 1/2 teaspoon ground cinnamon (optional, for lightly spiced dough)
• 3/4 cup (170 g) unsalted butter, softened to room temperature
• 3/4 cup (150 g) granulated sugar
• 1/4 cup (50 g) packed light brown sugar
• 1 large egg, at room temperature
• 1 1/2 teaspoons pure vanilla extract
• 1–2 tablespoons milk or heavy cream, as needed for soft dough

For the Cinnamon-Brown Sugar Filling

• 4 tablespoons (56 g) unsalted butter, very soft
• 1/2 cup (100 g) packed light brown sugar
• 1 1/2 tablespoons ground cinnamon
• 1/8 teaspoon fine salt

For the Vanilla Icing

• 1 cup (120 g) powdered sugar, sifted if lumpy
• 1/2 teaspoon pure vanilla extract
• 1 1/2–2 tablespoons milk (or cream) to thin
• Pinch of fine salt
• Optional: 1–2 teaspoons finely grated orange zest, for a citrus twist

Step-by-Step Instructions

Step 1: Make the cinnamon roll cookie dough

In a medium bowl, whisk together the flour, baking powder, salt, and ground cinnamon (if using). Set aside. In a large mixing bowl, add the softened butter, granulated sugar, and brown sugar. Beat with a hand mixer or stand mixer on medium speed for 2–3 minutes, until light, creamy, and slightly paler in color.

Add the egg and vanilla extract to the creamed butter mixture. Beat again on medium speed until fully combined and slightly fluffy, scraping down the sides of the bowl as needed. Turn the mixer to low and gradually add the dry ingredients in 2–3 additions. Mix just until the flour disappears and a soft dough forms. If the dough seems crumbly or too stiff to press together easily, mix in 1–2 tablespoons of milk or cream, just until the dough holds together and feels soft but not sticky.

Step 2: Shape and chill the dough

Turn the dough out onto a large sheet of parchment paper or plastic wrap. Gently press and pat it into a rough rectangle, about 1 inch (2.5 cm) thick. Wrap it completely and chill in the refrigerator for at least 1 hour, or up to 24 hours. Chilling firms the butter and makes the dough easier to roll, helping the spirals keep their shape in the oven.

If chilling longer than a few hours, let the dough sit at room temperature for 5–10 minutes before rolling so it is firm but pliable rather than rock-hard.

Step 3: Prepare the cinnamon-brown sugar filling

About 10 minutes before you plan to roll out the dough, make the filling. In a small bowl, combine the softened butter, brown sugar, cinnamon, and salt. Mash and stir with a fork until you have a smooth, spreadable paste with no dry pockets of sugar. If the butter is too cold and the mixture is crumbly, microwave it for just 5–10 seconds (you want it soft, not melted) and stir again until spreadable.

Set the filling aside at room temperature so it stays soft while you roll out the dough.

Step 4: Roll dough and spread the filling

Place a large piece of parchment paper on your work surface and lightly dust it with flour. Unwrap the chilled dough and place it on the parchment. Dust the top of the dough and your rolling pin with a light coating of flour to prevent sticking. Roll the dough into a neat rectangle about 9 × 12 inches (23 × 30 cm) and roughly 1/4 inch (0.6 cm) thick. Trim the edges with a knife or bench scraper if you want very even spirals; you can bake the scraps separately.

Using an offset spatula or the back of a spoon, gently spread the cinnamon filling evenly over the dough, going all the way to the long edges and leaving a 1/2-inch (1.25 cm) bare strip along one short edge. This bare strip will help seal the log. Starting from the opposite short edge, roll the dough up tightly into a log, using the parchment to help lift and roll. When you reach the bare strip, gently press to seal the seam.

Step 5: Chill the log and slice the spirals

Wrap the cookie log tightly in the parchment paper and place it on a baking sheet or cutting board so it stays straight. Chill in the refrigerator for 15–20 minutes, until firm enough to slice cleanly without squishing the spirals.

Meanwhile, preheat your oven to 350°F (175°C). Line 2 baking sheets with parchment paper. Unwrap the chilled log and use a sharp chef’s knife or serrated knife to slice it into 1/2-inch (1.25 cm) thick cookies. Slice using a gentle sawing motion so the log does not flatten. If any cookies look a bit squashed, reshape them into circles with your fingers. Arrange the spirals on the prepared baking sheets, leaving about 2 inches (5 cm) between cookies for slight spreading.

Step 6: Bake the cinnamon roll cookies

Bake one sheet at a time on the middle rack of the oven for 10–12 minutes, or until the cookies are just set around the edges and look slightly puffed and matte on top. They should still be pale; do not wait for them to brown deeply or they will lose their soft texture.

Remove the baking sheet from the oven and allow the cookies to cool on the pan for 5 minutes to firm up, then transfer them carefully to a wire rack to cool completely. Repeat with the remaining tray of cookies.

Step 7: Make and drizzle the vanilla icing

Once the cookies are completely cool to the touch, prepare the icing. In a small bowl, whisk together the powdered sugar, vanilla extract, 1 1/2 tablespoons of milk, salt, and optional orange zest until smooth and glossy. If the icing is too thick to drizzle in thin ribbons, add more milk a few drops at a time. If it is too thin, whisk in a spoonful of powdered sugar.

Place the cooled cookies on a wire rack set over a sheet of parchment or a tray to catch drips. Use a spoon or a small piping bag (or a zip-top bag with a tiny corner snipped off) to drizzle the icing in thin zigzags over each cookie, echoing the spiral shape. Let the icing set for 15–20 minutes at room temperature before serving or storing.

Pro Tips

• Chill twice for perfect spirals: Chilling the dough before rolling and again after shaping the log keeps the butter firm and helps the cookies hold a sharp, defined swirl.
• Roll evenly: Aim for a uniformly thick rectangle so the cookies bake evenly. Use a ruler if you like; 9 × 12 inches is a helpful guide.
• Use a sharp knife for slicing: A very sharp knife or serrated knife gives clean slices. Wipe the blade between cuts if the filling starts to build up.
• Do not overbake: Pull the cookies when the edges are set but still pale. They will finish setting as they cool and stay soft in the center.
• Control icing thickness: For delicate stripes, keep the icing on the thinner side; for thicker bakery-style drips, make it a bit stiffer.

Variations

• Cream cheese glaze: Replace 1–2 tablespoons of the powdered sugar with 1 ounce (28 g) very soft cream cheese and add a splash more milk for a tangy, cinnamon-roll-style icing.
• Maple cinnamon roll cookies: Swap half of the milk in the icing with pure maple syrup and add a tiny pinch of nutmeg for a warm, fall-inspired flavor.
• Chai-spiced swirl: Replace 1 teaspoon of the cinnamon in the filling with a mix of ground cardamom, ginger, and a pinch of cloves for a chai twist.

Storage & Make-Ahead

Store fully cooled and iced cookies in an airtight container at room temperature for up to 3–4 days, layering parchment between stacks to protect the icing. For longer storage, you can freeze the unbaked cookie log (well wrapped in plastic and then foil) for up to 2 months; thaw in the refrigerator until sliceable, then bake as directed. You can also freeze baked, undecorated cookies for up to 2 months and ice them after thawing. If you prefer to work ahead in smaller steps, make the dough and filling up to 24 hours in advance, keep them refrigerated, then roll, slice, and bake when you are ready.

Nutrition (per serving)

Approximate values per cookie (1 of 24), including icing: about 160 calories, 7 g fat, 3.5 g saturated fat, 22 g carbohydrates, 13 g sugar, 0.5 g fiber, 2 g protein, and 95 mg sodium. Actual values will vary based on exact ingredients, cookie size, and icing amount.