Description

This Cinnamon Cookie Recipe features soft and chewy cookies with a delightful cinnamon-sugar filling that oozes with every bite. The dough is rich and buttery, complemented by a sweet and spicy cinnamon filling frozen into small balls before folding into the dough. Rolled in cinnamon sugar, these cookies bake to perfection with a shiny cinnamon center and soft, matte edges, providing a taste reminiscent of cinnamon rolls in cookie form.

Ingredients

Scale

For the Filling

6 tablespoons salted butter, softened
3/4 cup brown sugar, packed
1 & 1/2 tablespoons cinnamon

For the Dough

1 cup salted butter (2 sticks), softened
1 and 2/3 cups granulated sugar
2 large eggs
2 teaspoons vanilla extract
3 and 1/2 cups all-purpose flour, spooned and leveled
1 teaspoon baking soda
3/4 teaspoon kosher salt
1 and 1/2 teaspoons cream of tartar

For Rolling

1/3 cup granulated sugar
1 and 1/2 tablespoons cinnamon

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Instructions

Prepare the filling: In a large bowl or stand mixer, beat 6 tablespoons softened butter until creamy and smooth. Add 3/4 cup packed brown sugar and 1 and 1/2 tablespoons cinnamon. Beat thoroughly, scraping down the sides until fully combined and smooth.
Freeze the filling balls: Line a baking sheet or platter with parchment paper or a silicone mat. Using a spoon, form small balls of the cinnamon filling about the size of marbles and line them up on the prepared pan. Freeze for 20 minutes until firm; if freezer space is limited, refrigerate for 1-2 hours until hardened.
Preheat the oven: Set the oven to 350°F (175°C) and prepare baking sheets lined with parchment paper or silicone mats.
Make the dough: In the same bowl (no need to wash), beat 1 cup softened butter for a couple of minutes until smooth. Add 1 and 2/3 cups granulated sugar and beat for 2 minutes until light and fluffy, scraping the bowl as needed. Add 2 eggs and 2 teaspoons vanilla extract; beat until smooth and uniform.
Mix dry ingredients: Spoon and level 3 and 1/2 cups flour into a bowl; stir in 1 teaspoon baking soda, 3/4 teaspoon kosher salt, and 1 and 1/2 teaspoons cream of tartar. Gently beat the dry mixture into the butter mixture just until combined with some flour streaks remaining. Scrape the sides and bottom of the bowl and beat a few more seconds until no streaks remain. Avoid over mixing.
Fold in cinnamon filling balls: Once the filling balls are firm, fold them gently into the dough using a wooden spoon or spatula—do not use a mixer. This keeps the filling intact distributed evenly throughout the dough.
Shape the cookies: Scoop dough balls about 2 inches across using a large cookie scoop or spoon, slightly overfilling the scoop. Prepare the cinnamon sugar by mixing 1/3 cup sugar and 1 and 1/2 tablespoons cinnamon in a bowl. Roll each dough ball in the cinnamon-sugar mixture to coat.
Arrange on baking sheets: Place the coated dough balls on prepared baking sheets, spacing about 2 inches apart to prevent excessive spreading. For safety, place 8 cookies per pan to allow room for spreading.
Bake the cookies: Bake at 350°F (175°C) for 11-12 minutes. The cinnamon filling will remain shiny and glossy, and edges of the cookie (without filling) will be firm but not golden, while the top edges will be matte, indicating doneness.
Shape immediately after baking: Within 30-60 seconds of removing from the oven, use spoons to push edges of each cookie toward the center, re-shaping the cookie and packing the oozing cinnamon filling back into the edges. This helps make the cookies thicker, chewier, and prevents spreading.
Cool and serve: Let cookies set on the pan for at least 5 minutes before transferring to a wire rack to cool completely. Enjoy warm with a glass of milk for the best experience.
Freezing instructions: For later use, shape dough into balls, roll in cinnamon sugar, and store in a ziplock bag in the freezer for up to 3 months. Bake directly from frozen, adding a couple of minutes to the baking time.

Notes

Do not overmix the dough to avoid tough cookies; stop mixing as soon as flour is fully incorporated.
Freezing the cinnamon filling balls before folding into dough prevents them from dissolving or melting during mixing and baking.
Immediately shaping the cookies after baking ensures a chewy texture and prevents the cinnamon filling from spreading too much.
You can bake cookies from frozen dough by increasing baking time slightly.
This recipe yields about 33 medium-sized cookies.
Store cookies in an airtight container at room temperature for up to 5 days or freeze for longer storage.
For thinner, crisper cookies, bake for an additional 1-2 minutes but be mindful the filling might spread more.

Nutrition

Serving Size: 1 cookie
Calories: 180
Sugar: 15g
Sodium: 110mg
Fat: 9g
Saturated Fat: 5g
Unsaturated Fat: 3g
Trans Fat: 0g
Carbohydrates: 23g
Fiber: 1g
Protein: 2g
Cholesterol: 30mg