Directions
<ol class="no-list-style"><li class="MethodStepper"><h4 class="step-title">Step 1</h4>Preheat your oven to 180°C (350°F) and line two large baking sheets with parchment paper. Position oven racks in the upper and lower thirds of the oven for even baking.</li><li class="MethodStepper"><h4 class="step-title">Step 2</h4>In a medium bowl, whisk together the flour, cocoa powder, baking soda, and salt until well combined. Sifting the cocoa powder will help prevent lumps and ensure a smooth cookie texture.</li><li class="MethodStepper"><h4 class="step-title">Step 3</h4>In the bowl of a stand mixer fitted with the paddle attachment, beat butter and sugar on medium-high speed until light and fluffy, about 3 minutes. This creaming process incorporates air into the mixture, giving your cookies a softer texture.</li><li class="MethodStepper"><h4 class="step-title">Step 4</h4>Add the egg and vanilla extract to the butter mixture, beating until fully incorporated, scraping down the sides of the bowl as needed. The mixture should look smooth and glossy.</li><li class="MethodStepper"><h4 class="step-title">Step 5</h4>With the mixer on low speed, alternately add the dry ingredients and buttermilk in three additions, beginning and ending with the dry ingredients. Mix just until combined – overmixing will develop the gluten and result in tough cookies. The batter should be thick but still somewhat spoonable, similar to a dense cake batter.</li><li class="MethodStepper"><h4 class="step-title">Step 6</h4>Using a 5cm (2-inch) cookie scoop or ice cream scoop, drop rounded mounds of batter onto the prepared baking sheets, spacing them about 5cm (2 inches) apart. You should get about 24 cookies for 12 sandwich pairs. If you don't have a scoop, use a tablespoon to measure approximately 2 tablespoons of batter per cookie.</li><li class="MethodStepper"><h4 class="step-title">Step 7</h4>Bake for 10-12 minutes, rotating the pans halfway through baking time, until the cookies spring back slightly when touched and a toothpick inserted into the center comes out clean. Be careful not to overbake – the cookies should remain soft and cake-like.</li><li class="MethodStepper"><h4 class="step-title">Step 8</h4>Allow cookies to cool on the baking sheets for 5 minutes before transferring to wire racks to cool completely. The cookies must be completely cool before filling to prevent the buttercream from melting.</li><li class="MethodStepper"><h4 class="step-title">Step 9</h4>While the cookies cool, prepare the raspberry buttercream. In a food processor or spice grinder, pulse the freeze-dried raspberries until they form a fine powder. Sift the powder to remove any seeds if desired (this creates a smoother filling).</li><li class="MethodStepper"><h4 class="step-title">Step 10</h4>In the bowl of a stand mixer fitted with the paddle attachment, beat the softened butter on medium-high speed until creamy and pale, about 3 minutes. Using freeze-dried raspberries rather than fresh ones gives intense flavor without adding excess moisture that would make the filling runny.</li><li class="MethodStepper"><h4 class="step-title">Step 11</h4>Gradually add the sifted powdered sugar, 120g at a time, mixing on low speed until incorporated. Add the raspberry powder, vanilla, salt, and 2 tablespoons of heavy cream. Increase speed to medium-high and beat for 3-4 minutes until light and fluffy. If the buttercream seems too stiff, add the remaining tablespoon of cream.</li><li class="MethodStepper"><h4 class="step-title">Step 12</h4>Match cookies in pairs of similar size. Transfer the buttercream to a piping bag fitted with a large round tip. Pipe a generous swirl of raspberry buttercream onto the flat side of one cookie from each pair, leaving a small border around the edge to allow for spreading when sandwiched.</li><li class="MethodStepper"><h4 class="step-title">Step 13</h4>Gently press the second cookie, flat side down, onto the buttercream to create a sandwich. Apply just enough pressure to spread the filling to the edges without squeezing it out.</li><li class="MethodStepper"><h4 class="step-title">Step 14</h4>For the best flavor and texture, refrigerate the assembled whoopie pies for at least 30 minutes to allow the flavors to meld. Bring to room temperature for about 15 minutes before serving for the optimal soft texture and flavor balance. Store in an airtight container in the refrigerator for up to 5 days, or freeze for up to 2 months.</li></ol>