Preheat oven to 350º F. Line sheet pan with parchment paper or silicon baking mat. Set aside.: The kitchen should smell faintly warm as the oven comes to temperature and the air in the room shifts; this preheating ensures even bake and accurate timing. You will know the oven is ready when the temperature stabilizes at 350º F , and using parchment paper prevents sticking and promotes even browning. A common error is skipping lining the pan, which can cause cookies to adhere and break when removed, so take the minute to prepare the pan ahead of time.
Cream together butter, cocoa and vegetable oil until well-combined. Stir in chocolate chips.: You will notice a glossy, darker paste form as the butter and cocoa marry, and the aroma of chocolate becomes more pronounced. The vegetable oil adds a silkiness that helps pockets of chocolate chips suspend in the dough. Avoid overbeating at this stage because excessive aeration can change the texture and lead to flatter cookies. If you see uneven lumps, stop and scrape the bowl, then mix briefly to even the texture.
Mix in flour, baking powder, and salt until well-combined. Add eggs, sugar and vanilla and mix until all well-combined and creamy.: The dry all-purpose flour will turn the glossy batter into a cohesive dough, and the faint scent of baking powder and salt will balance the sweetness. When you add the eggs , the mixture smooths into a creamy consistency and the sugar begins to dissolve, creating slight sheen. One mistake is to overmix after the flour goes in; that can develop gluten and make the cookies tough, so stop mixing as soon as the dough comes together.
Scoop tablespoon of cookie dough and drop onto prepared sheet pan, leaving about 1 1/2 inches between each for the cookies to spread as they bake.: As you scoop, the dough should feel slightly tacky but hold its shape, and the mounding will create domed cookies that flatten to the intended size. Proper spacing matters because the butter and shortening cause spreading; give each cookie about 1 1/2 inches of clearance so edges can crisp while centers stay tender. A frequent slip up is overcrowding the pan, which yields merged cookies instead of neat rounds.
Bake for 10 minutes. Remove from oven and allow to cool completely.: During baking you will see the edges set and darken slightly, and the tops may develop a subtle sheen. At the 10 minute mark the cookies should be browned at the edges but still tender in the center; they continue to set as they cool on the sheet, which is why removing at the right time is crucial. Leaving them in longer will create overly crisp interiors, while removing too early can leave them underdone and prone to collapsing.
While the chocolate cookie dough is baking, prepare the peppermint cream filling. Cream together all of the ingredients for the cream filling recipe. Set aside until the chocolate cookies portion has completely cooled.: As you beat the marshmallow cream , confectioners' sugar , peppermint extract , milk , and shortening , the mixture will lighten and become glossy, with the peppermint scent lifting through the bowl. The texture should be spreadable yet stable; chilling for a short time can firm it if it feels too soft. Beware of adding too much milk at once, which can make the filling runny and difficult to assemble.
Scoop 1 teaspoon of cream filling and place on top of the flattened side of one chocolate cookies. Place another chocolate cookie on top of the cream filling.: The filling should feel slightly cool and marshmallow soft, and when sandwiched it should create a modest mound without oozing. Press gently so the filling spreads to the edges but does not spill over. A common mistake is overfilling, which causes the sandwiches to slip apart and look messy, so keep to approximately 1 teaspoon per sandwich for neat presentation.
Serve at room temperature.: Allowing the sandwiches to rest brings the flavors into balance and softens any chill from refrigeration, yielding the best texture. At room temperature the mint aroma is more pronounced and the filling is perfectly pillowy. Serving too warm will make the filling too soft, while serving too cold can mute the peppermint and make biting more difficult.