Milk Chocolate-Filled Peanut Butter Sandwich Cookies

Peanut Butter Sandwich Cookies with Milk Chocolate Filling ~ A delightful double-duty cookie for anyone who loves the classic pairing of chocolate and peanut butter.

Peanut Butter Sandwich Cookies with Milk Chocolate Filling

These peanut butter sandwich cookies are perfect both as a comforting treat and as a welcome-home gesture. In my household they served both roles recently: a twofer of flavor and a special welcome for my husband returning from a short hospital stay.

I tend to bake constantly, but when a loved one falls ill baking takes a back seat. While he was in the hospital I found myself distracted and exhausted, worried for him and hoping the care team would respond quickly and compassionately. Fortunately, after a few uneasy days his pain was brought under control and he was scheduled to return home soon. Baking these cookies felt like a small, practical way to offer comfort.

Making these cookies with a young child is a sweet memory: after we finished a get-well card, we baked a batch and then prepared Lego soldiers and superheroes for an imaginary rescue mission. My three-year-old declared the cookies “I love these,” and that endorsement mattered more than any technical tasting note—though I can say that every recipe I’ve tried from Karen Damasco’s The Craft of Baking has been reliably excellent.

Practical notes before you bake:

  • These cookies are straightforward, but they take time. They bake best one sheet at a time and must be completely cool before filling.
  • Use smooth (creamy) peanut butter rather than chunky for the best texture and spreadability.
  • Follow the cooling instructions: let the cookies cool on the pan before transferring. Skipping this step can make the cookies sink or become misshapen.
  • The original method suggests rolling dough into balls by hand. If you’re baking with kids, piping small dollops from a pastry bag works well and saves time.
  • Filled cookies keep in an airtight container in the refrigerator for up to 3 days.
  • Unfilled cookies can be stored at room temperature in an airtight container for up to one week.

Peanut Butter Sandwich Cookies with Milk Chocolate Filling

Preheat the oven to 350 degrees F (175 degrees C). Line a baking sheet with parchment paper.

Ingredients:

Peanut Butter Cookies:

  • 1 ¾ cups unbleached all-purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ½ teaspoon kosher salt
  • 6 tablespoons unsalted butter, at room temperature
  • ½ cup plus 1 tablespoon lightly packed dark brown sugar
  • ¾ cup plus 1 tablespoon confectioners’ sugar
  • ½ cup creamy peanut butter
  • ½ cup vegetable oil
  • 1 ½ teaspoons vanilla extract
  • 1 large egg

Filling:

  • 6 oz. milk chocolate, chopped
  • ½ cup creamy peanut butter
  • ¼ cup confectioners’ sugar
  • ¼ teaspoon kosher salt
  • ¾ cup heavy cream

Instructions:

Peanut Butter Cookies:

  1. Sift the flour, baking powder, baking soda and salt into a bowl and set aside.
  2. In a large mixing bowl fitted with a paddle attachment, beat the butter, brown sugar and confectioners’ sugar on medium-high speed until light and fluffy, about 2 minutes. Add the peanut butter and mix until combined. With the mixer on low, slowly add the oil, vanilla and egg and beat briefly until incorporated. Add the flour mixture and mix until just combined.
  3. Transfer the dough to a pastry bag and pipe ½-inch dollops onto the prepared parchment, spacing them about 1 inch apart. Bake one sheet at a time at 350 degrees F until set and lightly golden around the edges. Remove from the oven and transfer to a wire rack. Allow the cookies to cool completely on the pan before filling.

Filling:

  1. Combine the chopped chocolate, peanut butter, confectioners’ sugar and salt in a heatproof bowl. In a small saucepan, bring the heavy cream to a gentle boil. Remove the cream from the heat and pour it over the chocolate mixture. Stir until the chocolate melts and the mixture is smooth and glossy.
  2. Cool the filling to room temperature, stirring occasionally, or set the bowl in an ice bath to speed cooling. The filling should thicken enough to spread between cookies. Use immediately, or store in an airtight container in the refrigerator for up to one week. If chilled, allow the filling to come to a spreadable consistency before assembling the sandwiches.

Recipe adapted from Karen Damasco, The Craft of Baking.