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Boston Cream Pie Cookies

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3.6 from 53 reviews

Transform simple cake mix into golden, soft cookies. Sandwich them around luscious, chilled vanilla pudding for the classic Boston flavor profile.

  • Total Time: 35 minutes
  • Yield: 4 servings 1x

Ingredients

Scale
  • 1 box Yellow cake mix (15.25 oz)
  • 1/3 cup Vegetable oil
  • 2 large Eggs
  • 1 package Instant vanilla pudding mix (3.4 oz)
  • 1 cup Cold milk
  • 1/4 teaspoon alcohol-free vanilla extract
  • 1/2 cup Semi-sweet chocolate chips
  • 2 tablespoons Heavy cream

Instructions

  1. Step 1: Preheat the oven to 350°F (175°C). In a large bowl, combine the yellow cake mix, vegetable oil, and eggs until a soft dough forms. Drop rounded teaspoons of dough onto parchment-lined baking sheets, spacing them 2 inches apart. Bake for 8-10 minutes until the edges are lightly golden. Allow cookies to cool completely on a wire rack.
  2. Step 2: Prepare the cream filling by whisking together the instant vanilla pudding mix, cold milk, and vanilla powder in a separate bowl until thickened (about 2 minutes). Refrigerate the pudding for 10 minutes to allow it to set firmly.
  3. Step 3: Once the cookies are cool, spread a generous spoonful of the set vanilla cream filling onto the flat side of half the cookies. Gently sandwich the filling with the remaining cookies to create the cookie pies.
  4. Step 4: Prepare the chocolate glaze. Combine the chocolate chips and heavy cream in a microwave-safe bowl. Microwave in 30-second intervals, stirring in between, until the chocolate is smooth and melted.
  5. Step 5: Dip the top surface of each assembled cookie sandwich into the chocolate glaze, allowing the excess to drip off. Place the finished cookies onto a tray and refrigerate for at least 30 minutes to set the glaze before serving.

Notes

  • Store these delicate cookie sandwiches in an airtight container in the refrigerator for up to 3 days, as the vanilla pudding filling is perishable.
  • For the best texture, allow the refrigerated cookies to sit at room temperature for 10 minutes before serving; this slightly softens the cream filling and cookie base.
  • When forming the dough, mix the yellow cake base only until just combined to ensure the baked cookies remain soft and cake-like rather than tough.
  • Pair these rich, creamy treats with a strong iced coffee or a classic glass of cold milk to balance the smooth filling and rich chocolate glaze.
  • Author: Kelli Rivers
  • Prep Time: 15 minutes
  • Cook Time: 20 minutes
  • Method: Stovetop
  • Cuisine: American