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Chocolate Sugar Cookie Sandwiches

These Chocolate Sugar Cookie Sandwiches are a whole new take on the classic cookie sandwich.  Soft sugar cookies are rolled in cinnamon sugar before baking.  Then, creamy cheesecake frosting is sprinkled with cinnamon and sandwiched between two of the cookies.  I'll take these over store-bought any day!
Prep Time15 mins
Cook Time9 mins
Total Time24 mins
Course: Dessert
Cuisine: American
Keyword: Cayenne Pepper, Chocolate Sugar Cookie, Cinnamon, Cinnamon Rolls, Cream Cheese Filling, Soft
Servings: 4 Sandwich Cookies
Author: Erin | Butter and Bliss


  • 4 tablespoons unsalted butter, room temperature
  • 2 tablespoons granulated sugar
  • 1/4 cup brown sugar light or dark
  • 1 large egg yolk
  • 1/2 teaspoon vanilla extract
  • 1/4 cup all-purpose flour
  • 3 tablespoons unsweetened cocoa powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/2 teaspoon ground cinnamon
  • 1/8 teaspoon ground cayenne pepper optional

Cinnamon Sugar Topping

  • 2 tablespoons granulated sugar
  • 1/2 teaspoon ground cinnamon

Cinnamon Cream Cheese Filling

  • 2 ounces cream cheese, room temperature
  • 2 tablespoons unsalted butter, room temperature
  • 1/2 teaspoon ground cinnamon
  • 2/3 cup powdered sugar


  • Preheat oven to 350F degrees and adjust the oven rack to the middle position. Line a baking sheet with parchment paper.
  • In a shallow dish, add the 2 tablespoons of sugar and 1/2 teaspoon of cinnamon for the cinnamon sugar topping. Mix together and set aside.


  • In a small mixing bowl, whisk together the flour, cocoa powder, baking soda, salt, cinnamon, and cayenne (if using). Note - I recommend sifting the ingredients into the bowl, then whisking. This helps remove any extra lumps.
  • In a medium mixing bowl, add the butter, brown sugar, and white sugar. Use a hand held mixer and beat on medium speed until combined and creamy. Add the egg yolk and vanilla extract and beat until the egg yolk is thoroughly combined.
  • Add the dry ingredients to the wet ingredients and beat on low speed until all of the dry ingredients are combined and no streaks remain.
  • Use a cookie scoop (or spoon) and scoop 8 equal dough balls. Roll the dough balls through the cinnamon sugar a couple of times, and place onto the prepared baking sheet, at least two inches apart. Bake for 9-11 minutes, until the edges are crisp, but the centers are still soft.
  • Cool on the baking sheet set on a wire cooling rack for 5 minutes. Then transfer the cookies to the wire cooling rack to cool completely.

Cinnamon Cream Cheese Filling

  • While the cookies are baking and cooling, prepare the filling.
  • In a small mixing bowl, add the cream cheese and butter. Use a hand held mixer and beat on medium speed until the mix is smooth and creamy. Sprinkle in the powdered sugar and cinnamon and beat on low speed until the filling is light and fluffy. The filling is ready to use immediately, or can be covered and refrigerated until ready to use.
  • To assemble the cookies, scoop 2-3 tablespoons (based on how much filling you like in the cookies, you may have extra filling) of the filling onto 4 of the cookies, then top with the remaining cookies to make the sandwiches. Enjoy!


  • Brown Sugar - Light or Dark brown sugar will work for this recipe.  I used light brown sugar to let the chocolate flavor shine through.
  • Cocoa Powder - Natural or Dutch processed cocoa powder will work for this recipe.