Chocolate Sugar Cookies (Homemade Oreos)

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With hints of the iconic childhood favorite, our Chocolate Sugar Cookies are a delicious Oreo copycat.

We took our best recipe Cut-Out Sugar Cookie Recipe and turned them into a rich, chocolate sugar cookie perfect for sandwiching with a layer of fluffy white vanilla cream frosting. While softer than an Oreo, these chocolate sandwich cookies are so much better. No fake tasting cream in the middle either!

The fluffy vanilla filling is made with butter, two kinds of sugar, vanilla and a touch of milk.

I don’t mind saying that I’m not a fan of icing made with shortening. The icky after-taste and mouthfeel is not a favorite. However to be a true Oreo copycat our filling had to have a nice fluffy texture and be little less creamy than a traditional buttercream icing. After a little research I found a recipe for cream filling by Martha Stewart that sounded perfect. With a few minor tweaks, we’re in business!  Using both powdered and granulated sugar provided the texture we’re looking for. The filling is fluffy and sweet, but not in a bad way!  You’ll find these chocolate sugar cookies have a familiar flavor and a unique personality.

Our chocolate sugar cookies (faux-reos) are great for gifting or packing in a lunchbox.

Make this recipe your own by cutting out any shape you need! Think smoldering hearts for Valentine’s Day or spooky cats for Halloween. We used a 2 1/2-inch fluted cookie cutter, but feel free to make them smaller if you want. You don’t have to sandwich them together either. Cut the cookies out a little thicker, and drizzle icing on top instead. No matter what shape or size you make, these cookies keep well for days. If you need to make these chocolate sugar cookies ahead of time, no worries, they freeze beautifully for up to three months! Just wait to decorate the cookies after they’re thawed. Your kiddos big and small will be thrilled to find a few of these treats tucked in their lunchbox or as an after school snack with a glass of cold milk.

Made with a few simple pantry ingredients and a combination of Dutch-process and black cocoa for deep, rich flavor.

We started with our basic sugar cookie recipe and tweaked it by replacing part of the flour with Dutch-process cocoa powder. Then we replaced half the cocoa with black cocoa powder giving these chocolate sugar cookies an intense, dark color and memorable flavor. To make sure you don’t miss all this lovely chocolate (haha) we’ve also added just a hint of espresso powder (found near the coffee in your local grocery store) which enhances the whole flavor profile.

Grab a glass of ice cold milk and dunk away!

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Chocolate Sugar Cookies (Homemade Oreos)

Prep Time: 20 minutes mins

Cook Time: 10 minutes mins

Total Time: 8 hours hrs 30 minutes mins

Yield: 24 sandwich cookies

Course: Cookies, Dessert

Author: Tricia

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5 from 4 votes

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Lightly sweet, dark chocolate cookies sandwiched with a fluffy vanilla cream filling - homemade Oreos!

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 *
• ⅛ 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.

Recipe 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

Here are a few more cookie recipes you might enjoy:

Everybody needs a great Cut-Out Sugar Cookie recipe that’s easy to make, tastes fantastic, and one that holds its shape when baked. We’ve got that perfect recipe right here! I’ve taken my mom’s old sugar cookie recipe and tweaked it into the BEST fool-proof sugar cookie recipe ever. Once you try this recipe, you’ll trust it always. Click HERE to get the recipe.

Classic Whoopie Pies ~ Chocolate cake-like batter is baked into large, soft hamburger-sized, bun shaped cookies then filled with a fluffy, sweet marshmallow frosting. Click HERE to get the recipe.

Oatmeal Cream Pies – soft, chewy oatmeal cookies with hints of cinnamon, molasses and coconut, with a sweet marshmallow cream filling. Click HERE to get the recipe.

Thanks so much for stopping by!  Tricia