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Homemade Chocolate Sandwich Cookies with purple, green, and orange frosting.
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Homemade Chocolate Sandwich Cookies

A recipe for Homemade Chocolate Sandwich Cookies! These dark chocolate cookies are filled with a sweet vanilla buttercream for a fun homemade treat.
Course Dessert
Cuisine American
Keyword buttercream, chocolate, cookie, dark chocolate, dessert, fall, halloween, oreo, vanilla
Prep Time 30 minutes
Cook Time 9 minutes
Resting Time: 1 hour
Total Time 1 hour 39 minutes
Servings 23 Sandwich Cookies

Ingredients

Dark Chocolate Cookies:

  • 1 cup (226 grams) unsalted butter softened at room temperature
  • 3/4 cup (150 grams) granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 cups (250 grams) all-purpose flour
  • 1/2 cup (50 grams) black or dark cocoa powder
  • 1/4 teaspoon salt

Vanilla Buttercream:

  • 8 tablespoons (113 grams) unsalted butter softened at room temperature
  • 2 cups (260 grams) powdered sugar
  • Pinch salt
  • 1 teaspoon vanilla extract
  • 2 teaspoons (10 milliliters) heavy cream
  • Food coloring if desired

Instructions

To make the dark chocolate cookies:

  • In the bowl of a stand mixer fitted with a paddle attachment or a large bowl, beat together the softened butter and sugar until light and fluffy.
  • Beat in the egg, followed by the vanilla extract.
  • In a medium bowl, combine the flour, dark cocoa powder, and salt. Beat into the butter mixture until just combined with no streaks remaining and a dough is formed.
  • Transfer the dough to a piece of plastic wrap and pat into a disc. Wrap in the plastic and refrigerate 1-2 hours until chilled.
  • Preheat oven to 350˚F (180˚C). Line two baking sheets with parchment or lightly grease.
  • Once chilled and no longer sticky when touched, remove the dough from the plastic wrap and place between two large pieces of parchment.
  • Roll the dough into a large sheet about 1/8-1/4 inch (3-6 millimeters) thick.
  • Gently remove the top parchment sheet and cut the dough into circles using a plain or fluted 2 1/2 inch (6 centimeter) round cutter.
  • Carefully transfer the rounds to the prepared baking sheets about 1 inch (2.5 centimeters) apart. If desired, stamp the top of the cookie with a design, taking care not to push all the way to the bottom.
  • Collect the scraps of cookie dough and roll out again between two sheets of parchment to make more cookies. If too soft to handle, refrigerate for about 30 minutes.
  • Bake the cookies in the preheated oven until set, about 8-10 minutes.
  • Allow to rest on cookie sheet for 5 minutes before transferring to a wire rack to cool to room temperature. Repeat with remaining dough.

To make the Vanilla Buttercream:

  • In the bowl of a stand mixer fitted with a whisk attachment or a large bowl, beat together the butter and powdered sugar until light and fluffy.
  • Beat in the salt, followed by the vanilla.
  • Slowly add the heavy cream to reach desired consistency.
  • If coloring the buttercream, divide the frosting evenly into three (or desired amount) bowls. Add food coloring, on drop at a time, and fold in to create the desired shade of color.
  • Transfer the buttercream into piping bags or a ziplock bag with a piece of the corner snipped off.

To assemble:

  • Pair together the cooled dark chocolate cookies that are similar in shape.
  • Pipe the buttercream filling onto half of the bottom side of the cookies. Top, bottom side towards filling, with remaining cookies.
  • Gently twist until the buttercream filling reaches the edges. Repeat with remaining pairs.
  • Allow the cookies to rest for 30 minutes to 1 hour to set the filling before serving or store in an airtight container at room temperature in a cool, dark place for up to 3 days.