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5 from 4 votes

Chocolate Sugar Cookies (Homemade Oreos)

Lightly sweet, dark chocolate cookies sandwiched with a fluffy vanilla cream filling - homemade Oreos!
Prep Time20 mins
Cook Time10 mins
Overnight refrigeration8 hrs
Total Time8 hrs 30 mins
Course: Cookies, Dessert
Cuisine: American
Keyword: chocolate, sugar cookie
Servings: 24 sandwich cookies
Calories: 268kcal
Author: Tricia

Ingredients

For the cookies:

  • 1 cup unsalted butter, room temperature
  • 1 ounce cream cheese, room temperature
  • 1 cup granulated sugar
  • 1 large egg
  • 1 ½ teaspoons vanilla extract
  • 2 ½ cups all-purpose flour
  • ¼ cup Dutch-process cocoa powder
  • ¼ cup black cocoa *
  • teaspoon espresso powder (optional)
  • 1 ½ teaspoons baking powder
  • 1 teaspoon salt
  • Parchment paper

For the filling:

  • 8 tablespoons unsalted butter, room temperature
  • ½ cup granulated sugar
  • 3 cups powdered sugar
  • 2 teaspoons vanilla extract
  • 2 teaspoons milk or cream, more or less as needed for desired consistency

Instructions

To prepare the cookies:

  • In a large mixing bowl beat butter and cream cheese together with an electric mixer until well blended. Add the sugar and beat until light and fluffy. Add the egg and vanilla and beat until combined.
  • In a small bowl whisk together the flour, cocoa powders, espresso powder, baking powder and salt. Add half the flour mixture to the butter and sugar and blend on low until incorporated. Add the final half of the flour mixture and beat until a soft dough forms. Add additional flour, one tablespoon at a time until the dough is soft and no longer sticky. For best results, do not add more than one or two additional tablespoons of flour or the cookies may be dry. The dough will firm up when refrigerated.
  • Gather the dough into a ball and cut into four pieces. Press one ball of dough onto a piece of parchment paper. Cover with a second piece of parchment. Using a rolling pin, roll the dough to ⅙ or ¼ inch thickness. Place the entire sheet of parchment and rolled out cookie dough onto a large baking sheet so the dough will be flat. Repeat with the remaining three pieces of cookie dough, stacking the rolled out dough on top of each other. Refrigerate the dough for at least 8 hours, or up to two days.
  • Preheat oven to 350°F. Line two baking sheets with parchment paper and set aside.
  • When ready to bake, remove one disc of cookie dough from the refrigerator and cut into the desired shapes. Transfer the unbaked cookies to the prepared baking sheet about 2-inches apart. Gather any scraps together and refrigerate until you’ve cut out all the remaining dough.
  • Bake for 8 to 10 minutes (depending on the size and thickness of the cookie or until the cookies are set and you start to smell chocolate. For best results, do not over-bake! Cool on the pan for 3-4 minutes then remove to a wire rack to cool completely before filling. Repeat will all remaining dough. Gather the dough scraps together and roll out on parchment. Refrigerate or freeze for 10 minutes, then cut and bake.

To prepare the filling:

  • In a medium mixing bowl beat the butter until light and fluffy. Add the granulated sugar and vanilla and beat until combined. Add half the powdered sugar and mix on low until incorporated. Add the remaining powdered sugar and mix again, scraping down the sides of the bowl as needed. Add the milk, one teaspoon at a time until you reach a creamy but firm consistency.

To assemble the cookies:

  • Using a small cookie scoop, dollop about 2 tablespoons (a heaping cookie scoop) of filling onto the center of half the cookies. Top with remaining cookies and gently press and twist until the filling reaches the edges. Repeat.

Notes

  • For these cookies I used a 2-1/2 inch fluted cookie cutter and rolled the dough to 1/6th inch thickness.
  • Do not put unbaked cookies on a hot cookie sheet until ready to bake. It will cause them to spread.
  • DO NOT OVER-BAKE! The cookies should be just set and you should smell chocolate.
  • Baking time will vary depending on the size, width and thickness of the cookies.
  • Refrigerate filled cookies until ready to serve.
  • Baked, cooled, unfilled cookies can be frozen for up to 3 months.
  • These cookies make great ice cream sandwiches too. Fill with your favorite ice cream and freeze until firm. Store in an airtight container in the freezer for up to 3 months.
Filling recipe adapted from Martha Stewart
* Use black or dark cocoa powder, or all Dutch processed cocoa if desired.
Nutrition information is calculated using an ingredient database and should be considered an estimate. When multiple ingredient alternatives are given, the first listed is calculated for nutrition. Garnishes and optional ingredients are not included.

Nutrition

Calories: 268kcal | Carbohydrates: 39g | Protein: 2g | Fat: 12g | Saturated Fat: 8g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 3g | Trans Fat: 1g | Cholesterol: 39mg | Sodium: 133mg | Potassium: 51mg | Fiber: 1g | Sugar: 27g | Vitamin A: 379IU | Calcium: 25mg | Iron: 1mg