Preheat oven to 375°. Line baking sheets with parchment paper.: When you heat the oven to 375° the air becomes steady and ready to create even rise and set the cookie edges, producing that slightly firm outer rim and soft center. You'll notice the kitchen warms and the first scent of cocoa pops when the oven is on, which signals the environment is correct for predictable texture. If you skip preheating the cookies may spread unevenly and bake longer, so always wait until the oven reaches temperature before placing pans inside.
For cookies: In a medium bowl, whisk together flour, cocoa, salt, baking powder, and baking soda.: In a medium bowl, whisk together flour, cocoa, salt, baking powder, and baking soda : As you whisk these dry components they take on a uniform color and texture, and the aroma of the cocoa becomes more pronounced. This step is crucial because evenly distributed leaveners ensure consistent rise and tenderness in every cookie. A common mistake is not sifting or whisking, which can leave pockets of baking soda and create bitter spots or uneven domes, so make sure the mixture looks homogenous.
In a large bowl, beat butter and granulated sugar with a mixer on medium speed until fluffy. Add eggs, one at a time, beating until combined. Beat in vanilla.: As the butter and sugar cream, you will see the mixture lighten in color and texture, looking pale and airy, which traps air for lift. Adding eggs one at a time ensures they emulsify properly, creating a stable batter that holds structure. If the butter is too warm the mixture will appear oily rather than fluffy, and the cookies will spread too much, so start with properly softened butter.
Gradually add flour mixture to butter mixture alternately with buttermilk, beginning and ending with flour mixture, and beating just until combined after each addition.: Alternate additions create a tender crumb by minimizing gluten development, and the batter will feel slightly thick but scoopable when done. You'll know it's right when the batter pulls away from the bowl and the color is even. Overmixing at this stage makes cookies dense and tough, so stop as soon as dry streaks disappear.
Using a 1-tablespoon spring-loaded scoop, scoop batter 2 inches apart onto prepared pans. Bake until top and edges are set, 8 to 10 minutes. Let cool on pans for 5 minutes. Remove from pans, and let cool completely on wire racks.: The batter will form neat domes that spread a little, and the edges will set first, giving a slightly firmer perimeter. As they bake you'll hear the quiet settling sound and see a subtle sheen on the tops when they are ready. A common error is baking too long, which dries them out, so watch closely around the 8 minute mark and test by gently touching the edge for spring.
For filling: In a medium bowl, beat marshmallow crème and butter with a mixer on medium speed until smooth and combined. Beat in confectioners’ sugar, extracts, and salt until smooth and well combined, stopping to scrape beaters and bowl. Stir in half of crushed peppermint bark.: In a medium bowl, beat marshmallow crème and butter with a mixer on medium speed until smooth and combined. Beat in confectioners’ sugar, extracts, and salt until smooth and well combined, stopping to scrape beaters and bowl. Stir in half of crushed peppermint bark : The filling transforms into a glossy, spreadable cream with a sweet, aerated texture; you will smell peppermint and vanilla as you combine them. Folding in half the crushed bark adds flecks of crunchy texture that punctuate the sweetness. Watch for overbeating which can thin the filling, and if needed chill briefly to firm up before sandwiching to avoid slippage.
Spread 1 1/2 to 2 tablespoons filling onto flat side of half of cookies. Top with remaining cookies, flat side down, gently pressing until filling reaches the edges. Roll edges in remaining crushed peppermint bark. Refrigerate in an airtight container for up to 5 days.: The filling should feel silky and cool as you spread it, and it holds shape against the cookie without sliding off. Use the specified amount to achieve a balanced bite, and press gently when you top with the second cookie to avoid squashing the texture. Too much filling can push out and create a messy edge, so measure for uniform sandwiches.
Top with remaining cookies, flat side down, gently pressing until filling reaches the edges: As you assemble the pies you will hear a soft smush and see the filling meet the edges, creating a neat sandwich. Gentle pressure ensures an even distribution of filling without crushing the airy cookie. Pressing too hard will flatten the cookies and change the intended texture, so use a light touch until you see filling at the edge.
Roll edges in remaining crushed peppermint bark: Rolling the edges adds bright color and a crunchy contrast, and you will feel the tiny shards adhere to the sweet buttercream. This final flourish makes each pie festive and texturally interesting. If the filling is too soft the bark will not stick, so chill slightly if necessary before rolling to ensure it adheres.
Refrigerate in an airtight container for up to 5 days: Cooling and storing the sandwiches allows the flavors to meld and the filling to firm, and the cookies will maintain their tenderness while the bark keeps its crunch. Store them flat and avoid stacking too many layers to prevent squashing. A common pitfall is leaving them uncovered, which will dry out the cookies, so use an airtight container.