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Soft, cake-like cookies sandwiching a creamy vanilla filling, topped with a glossy chocolate glaze, inspired by the classic Boston Cream Pie dessert.

  • Total Time: 1 hour
  • Yield: 24 sandwich cookies (48 cookies before assembly) 1x

Ingredients

Scale
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract (for the dough)
  • 2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1 cup heavy cream
  • 1/2 cup powdered sugar
  • 1 teaspoon vanilla extract (for the cream filling)
  • 1 cup semi-sweet chocolate chips
  • 1 tablespoon vegetable oil

Instructions

  1. Beat softened unsalted butter and granulated sugar on medium speed until light, fluffy, and pale, about 3–4 minutes.
  2. Add eggs one at a time, mixing fully after each, then stir in vanilla extract for the dough.
  3. Whisk together all-purpose flour, baking powder, baking soda, and salt in a separate bowl.
  4. Slowly add the dry ingredients to the butter mixture on low speed and mix just until combined.
  5. Wrap the dough tightly and chill in the refrigerator for at least 30 minutes.
  6. In a chilled bowl, combine heavy cream, powdered sugar, and vanilla extract; whip with a mixer to stiff peaks (about 3–5 minutes) and refrigerate until ready to assemble.
  7. Preheat the oven to 350°F (175°C) and line baking sheets with parchment paper.
  8. Scoop rounded dough balls onto the prepared sheets, spacing about 2 inches apart.
  9. Bake for 10–12 minutes until edges are lightly golden and centers appear slightly soft.
  10. Cool the cookies on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
  11. Combine semi-sweet chocolate chips and vegetable oil in a microwave-safe bowl and heat in 30-second increments, stirring between bursts, until melted and smooth; let cool until pourable.
  12. Place one cookie flat side up, dollop or pipe a generous spoonful of chilled whipped cream on it, then top with a second cookie flat side down and press lightly to spread the filling; repeat for remaining cookies.
  13. Dip the tops of the assembled sandwiches into the melted chocolate or spoon the glaze over them, let excess drip off, and set them on parchment or a rack to harden.
  14. Let the chocolate set at room temperature or chill the cookies in the refrigerator for 5–10 minutes to firm the glaze.

Notes

Chill dough for at least 30 minutes to keep cookies from spreading and to achieve a soft, cake-like texture., Mix dry ingredients into wet only until combined to avoid tough cookies., Stop whipping cream once stiff peaks form to prevent graininess., Stabilize cream filling with instant pudding mix or cream cheese for longer shelf life., Heat chocolate glaze gently to avoid seizing and add vegetable oil for smoothness and shine., Ensure cookies are cool before glazing to prevent melting chocolate., Leave at least 2 inches between dough balls on baking sheet to prevent sticking., For sturdier filling, substitute whipped cream with cooled pastry cream., Variations include using dark or milk chocolate for glaze, adding almond extract or espresso powder for flavor twist, and adding a thin layer of fruit jam under cream filling., Gluten-free flour blend can replace all-purpose flour; adjust baking time and chill dough well.

  • Author: Laura
  • Prep Time: 20 minutes plus 30 minutes chilling time
  • Cook Time: 10-12 minutes per batch
  • Category: Dessert

Nutrition

  • Serving Size: 1 sandwich cookie
  • Calories: Approximately 180 calories per sandwich cookie
  • Fat: Approximately 9 grams per serving
  • Carbohydrates: Approximately 25 grams per serving
  • Protein: Approximately 3 grams per serving