Old-Fashioned Homemade Chocolate Sandwich Cookies
These old-fashioned homemade chocolate sandwich cookies are a from-scratch version of a childhood favorite. Soft chocolate cookies are filled with a sweet vanilla cream filling for a nostalgic treat made with simple pantry ingredients.
Servings: 25 cookies
Calories: 244kcal
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Equipment
Ingredients
Chocolate Cookies
- 2½ Cups All-Purpose Flour
- ½ Cup Unsweetened Cocoa Powder
- 1 Teaspoon Baking Soda
- ½ Teaspoon Baking Powder
- ¼ Teaspoon Salt
- ½ Cup Unsalted Butter softened
- ¾ Cup Granulated Sugar
- ¼ Cup Light Brown Sugar packed
- 1 Large Egg
- 1 Teaspoon Vanilla Extract
- 2 Tablespoons Milk
Cream Filling
- ½ Cup Unsalted Butter softened
- ½ Cup Vegetable Shortening
- 3 Cups Powdered Sugar
- 2 Teaspoons Vanilla Extract
- 2 Teaspoons Milk
Instructions
Prepare the Chocolate Cookies
- Preheat your oven to 350°F. Line two baking sheets with parchment paper or silicone baking mats to prevent sticking and make cleanup easier.
- Mix the Dry Ingredients. In a large bowl, whisk together the flour, cocoa powder, baking soda, baking powder, and salt until everything is evenly combined. Set aside.2½ Cups All-Purpose Flour, ½ Cup Unsweetened Cocoa Powder, 1 Teaspoon Baking Soda, ½ Teaspoon Baking Powder, ¼ Teaspoon Salt
- Cream the Butter and Sugars. In a separate large bowl, use a stand mixer or hand mixer to beat the softened butter, granulated sugar, and brown sugar until the mixture becomes light and fluffy, about 2 to 3 minutes.½ Cup Unsalted Butter, ¾ Cup Granulated Sugar, ¼ Cup Light Brown Sugar
- Beat in the egg, vanilla extract, and milk until fully incorporated, scraping down the sides of the bowl as needed.1 Large Egg, 1 Teaspoon Vanilla Extract, 2 Tablespoons Milk
- Gradually add the dry ingredients to the wet mixture, mixing on low speed until no dry streaks remain and a soft, thick dough forms. Avoid overmixing.
- Shape the Cookies. Scoop about 1 tablespoon of dough for each cookie and roll into smooth balls. Arrange them about 2 inches apart on the prepared baking sheets.
- Using the flat bottom of a measuring cup or drinking glass, gently flatten each dough ball to about ½-inch thick. If the dough begins to stick, lightly dust the bottom of the cup with cocoa powder or flour. This recipe makes about 50 cookie halves for a total of 25 filled cookies.
- Bake for 6 to 7 minutes, just until the cookies are set around the edges. The centers will still look soft, and that's exactly what you want for a tender sandwich cookie.
- Allow the cookies to cool on the baking sheet for 3 minutes before transferring them to a wire rack to cool completely.
Prepare the Vanilla Cream Filling
- In a clean mixing bowl, beat the softened butter and vegetable shortening until smooth and creamy.½ Cup Unsalted Butter, ½ Cup Vegetable Shortening
- Gradually add the powdered sugar, mixing well after each addition. Blend in the vanilla extract and milk, then continue beating until the filling is light, fluffy, and easy to pipe.3 Cups Powdered Sugar, 2 Teaspoons Vanilla Extract, 2 Teaspoons Milk
Assemble the Sandwich Cookies
- Transfer the filling to a piping bag or a zip-top bag with one corner snipped off. Pipe a generous swirl onto the flat side of half of the cooled cookies.
- Top each with another cookie and gently press together until the filling reaches the edges.
- Store the finished cookies in an airtight container at room temperature for up to 5 days, or freeze them for longer storage.
Notes
Ingredient Notes
Unsweetened Cocoa Powder Use a good-quality natural unsweetened cocoa powder for rich chocolate flavor. Brown Sugar Brown sugar helps keep the cookies soft and chewy long after baking. Butter Room-temperature butter mixes more evenly and creates a tender cookie. Vegetable Shortening Shortening helps the filling stay fluffy and stable, especially during warm weather. Vanilla Extract Pure vanilla adds classic bakery flavor to the cream filling.Tips for Success
- Measure flour by spooning it into the measuring cup instead of scooping directly from the bag.
- Don't overmix once the flour is added.
- Remove the cookies while they still look soft in the center.
- Allow cookies to cool completely before filling.
- Match similar-sized cookies together before assembling.
- Pipe the filling for an even, bakery-style appearance.
Nutrition
Calories: 244kcal | Carbohydrates: 33g | Protein: 2g | Fat: 12g | Saturated Fat: 6g | Polyunsaturated Fat: 2g | Monounsaturated Fat: 4g | Trans Fat: 1g | Cholesterol: 27mg | Sodium: 62mg | Potassium: 52mg | Fiber: 1g | Sugar: 22g | Vitamin A: 240IU | Vitamin C: 0.002mg | Calcium: 16mg | Iron: 1mg