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Cinnamon Cookie Delight Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.9 from 19 reviews
  • Author: Madison
  • Prep Time: 25 minutes
  • Cook Time: 12 minutes
  • Total Time: 37 minutes
  • Yield: 33 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Description

This recipe delivers the best cinnamon cookies with a creamy cinnamon sugar filling that stays soft and gooey inside. The dough is buttery, lightly sweet, and wrapped around frozen cinnamon-sugar filling balls, then rolled in cinnamon sugar before baking for a perfect chewy texture and rich cinnamon flavor. These cookies offer a delightful cinnamon roll experience in cookie form, making them the ultimate treat.


Ingredients

Units Scale

For the filling

  • 6 tablespoons salted butter, softened
  • 3/4 cup brown sugar, packed
  • 1 and 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

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 and 1/2 tablespoons cinnamon. Beat well, scraping the sides down, until the mixture is completely smooth.
  2. Freeze the filling balls. Line a baking sheet with parchment paper or a silicone mat. Use a spoon to form small cinnamon filling balls about the size of a marble and place them on the prepared sheet. Freeze for 20 minutes until hardened. If using the refrigerator instead of freezer, chill for 1 to 2 hours until firm.
  3. Preheat the oven. Set the oven to 350 degrees Fahrenheit and prepare additional baking sheets with parchment paper or silicone mats for baking the cookies.
  4. Make the dough. In the same large bowl or stand mixer (no need to wash), beat 1 cup softened butter for a couple of minutes until smooth, scraping the sides occasionally. Add 1 and 2/3 cups granulated sugar and beat for 2 minutes until light and fluffy with no sugar chunks.
  5. Add eggs and vanilla. Beat in 2 large eggs and 2 teaspoons vanilla extract until the mixture is smooth and homogeneous, scraping the bowl as needed.
  6. Mix dry ingredients. Spoon and level 3 and 1/2 cups all-purpose flour into a bowl. Stir in 1 teaspoon baking soda, 3/4 teaspoon kosher salt, and 1 and 1/2 teaspoons cream of tartar. Gradually add this flour mixture to the wet ingredients and beat gently. Stop mixing when the dough is just combined and only slight flour streaks remain. Scrape down sides and mix a few more seconds without overmixing.
  7. Fold in the frozen cinnamon filling balls. Using a wooden spoon or spatula (not a mixer), gently fold the frozen cinnamon filling balls into the dough until evenly distributed.
  8. Shape the cookies. Use a large cookie scoop or spoon to portion dough balls about 2 inches across. Overfill the scoop slightly for the right size.
  9. Roll cookies in cinnamon sugar. In a small or medium bowl, combine 1/3 cup granulated sugar and 1 and 1/2 tablespoons cinnamon. Roll each dough ball in the cinnamon-sugar mixture to coat.
  10. Arrange cookies for baking. Place cookie dough balls on prepared baking sheets, spacing about 2 inches apart. For safety, place 8 cookies per pan to prevent spreading into one another.
  11. Bake the cookies. Bake at 350 degrees Fahrenheit for 12 minutes. The cookies will not look fully done because the cinnamon filling remains shiny. The edges without filling should be firm but not golden, and the cookie tops should appear matte on the outer edges.
  12. Shape cookies after baking. Within 30 to 60 seconds of removing the cookies from the oven and before edges crisp, use two spoons to push the cookie edges toward the center. Gather any oozing cinnamon filling and pack it into the edges to shape the cookies into thick, chewy circles.
  13. Cool and serve. Let cookies set on the baking sheet for at least 5 minutes, then transfer to a wire rack to cool. Enjoy warm with a glass of milk.
  14. Freezing instructions. 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 minutes to baking time.

Notes

  • Use room temperature butter for smooth creaming in dough and filling.
  • Do not overmix dough to avoid tough cookies; mix just until combined.
  • Freeze the filling balls solid to prevent them from melting into the dough too soon during baking.
  • Shaping cookies immediately after baking keeps them thick and chewy.
  • For best results, use parchment paper or silicone mats to prevent sticking.
  • You can safely bake frozen cookie dough without thawing, you just need to increase bake time by 2-3 minutes.
  • If kosher salt is unavailable, use regular sea salt but reduce slightly to 1/2 teaspoon.
  • For extra cinnamon flavor, incrementally adjust cinnamon amounts to taste.
  • These cookies pair perfectly with milk or a light tea.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180 kcal
  • Sugar: 15 g
  • Sodium: 110 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