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Cinnamon Cookie Recipe with Filling Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.8 from 9 reviews
  • Author: Caroline
  • Prep Time: 25 minutes
  • Cook Time: 12 minutes
  • Total Time: 37 minutes
  • Yield: 33 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Description

These cinnamon cookies are soft, chewy, and packed with a gooey cinnamon sugar filling that makes them irresistibly delicious. Perfectly baked to maintain a tender texture with a beautiful cinnamon-sugar coating and a warm, spiced center.


Ingredients

Units 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 2/3 cups granulated sugar
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 3 1/2 cups all-purpose flour, spooned and leveled
  • 1 teaspoon baking soda
  • 3/4 teaspoon kosher salt
  • 1 1/2 teaspoons cream of tartar

For rolling

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

Instructions

  1. Make 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 1/2 tablespoons cinnamon. Beat well, scraping sides, until completely smooth.
  2. Shape and freeze filling: Line a baking sheet with parchment paper or a silicone mat. Use a spoon to form small marble-sized balls of the filling and line them up on the pan. Freeze for 20 minutes until hardened. If freezer space is limited, refrigerate for 1-2 hours until firm.
  3. Preheat oven and prepare pans: Preheat oven to 350 degrees Fahrenheit. Line 2 baking sheets with parchment paper or silicone mats.
  4. Make the dough: In the same bowl, beat 1 cup softened butter for a couple of minutes until smooth. Add 1 2/3 cups granulated sugar and beat for 2 minutes, scraping the bowl frequently until light and fluffy. Add 2 eggs and 2 teaspoons vanilla extract, beating until smooth and homogenous.
  5. Combine dry ingredients: In a separate bowl or in the spooned and leveled 3 1/2 cups flour, stir in 1 teaspoon baking soda, 3/4 teaspoon kosher salt, and 1 1/2 teaspoons cream of tartar with a small spoon. Gently beat the flour mixture into the butter mixture, stopping when most flour streaks disappear to avoid over mixing.
  6. Incorporate cinnamon filling balls: Fold the frozen cinnamon filling balls gently into the dough using a wooden spoon or spatula, avoiding mixers to prevent breaking.
  7. Shape the cookies: Use a large cookie scoop or spoon to form dough balls about 2 inches across and slightly overfilled.
  8. Prepare cinnamon-sugar coating: In a medium bowl, mix 1/3 cup granulated sugar and 1 1/2 tablespoons cinnamon. Roll each dough ball in this mixture to coat evenly.
  9. Arrange on baking sheets: Place the coated dough balls on prepared baking sheets with about 2 inches of space between each cookie, fitting 8-12 cookies per sheet safely.
  10. Bake the cookies: Bake at 350 degrees Fahrenheit for 12 minutes. The cookies won’t look fully done due to the shiny cinnamon filling but the edges should be firm and the outer top matte.
  11. Shape immediately after baking: Within 30-60 seconds of removing from oven, use spoons to gently push the edges of each cookie toward the center, packing in any oozing cinnamon filling to maintain thickness and chewiness.
  12. Cool and serve: Let the cookies set on the baking sheet for at least 5 minutes before transferring to a wire rack. Enjoy warm with a glass of milk.
  13. Storage and freezing: Dough balls can be frozen rolled in cinnamon sugar in a ziplock bag for up to 3 months. Bake from frozen, adding 2 minutes to the baking time.

Notes

  • Use softened butter for best creaming results in both dough and filling.
  • Do not overmix the dough to avoid tough cookies; a few flour streaks before final mixing is ideal.
  • Freezing the cinnamon filling balls solidifies them, preventing them from melting into the dough too quickly during baking.
  • Shaping cookies immediately after baking helps keep them thick and chewy instead of spreading thin.
  • Use parchment paper or silicone mats for easy cleanup and to prevent sticking.
  • For consistent cookie size, use a large cookie scoop for dough balls approximately 2 inches wide.
  • If freezer space is limited, refrigerate cinnamon filling balls until firm but freezing is preferred for best shaping.
  • Experiment with different cinnamon levels in the filling and coating to suit your taste.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180 kcal
  • Sugar: 14 g
  • Sodium: 100 mg
  • Fat: 9 g
  • Saturated Fat: 5 g
  • Unsaturated Fat: 3 g
  • Trans Fat: 0 g
  • Carbohydrates: 24 g
  • Fiber: 1 g
  • Protein: 2 g
  • Cholesterol: 30 mg