Preparation Steps

• In a stand mixer with a paddle attachment, cream the room-temperature butter and powdered sugar together on medium speed until light and fluffy, about 2 minutes. Add the cocoa powder, salt, and vanilla, and mix until fully incorporated. Gradually add the flour, half initially, then the rest 0.25 cup at a time, until a stiff, dry dough forms. Divide the dough in half, shape each into a disk, wrap in plastic wrap, and refrigerate for 15 minutes.
• Preheat oven to 350°F (175°C). Roll out one chilled dough disk between two sheets of parchment paper to 0.25 inch thickness. Use a 2-inch round cookie cutter to cut circles. Place on a parchment-lined baking sheet and bake for 9 minutes. Avoid overbaking to prevent bitterness. Cool completely on a wire rack. Repeat with remaining dough.
• While cookies cool, prepare the filling. Pulse the unwrapped candy canes in a food processor until fine dust. In a stand mixer, cream the softened butter, vanilla, and half of the powdered sugar until fluffy. Add the remaining powdered sugar and candy cane dust, mixing well. Add milk or cream gradually until the filling is thick but spreadable. Transfer to a piping bag with a large round tip.
• To assemble, pair cooled cookies by size. Pipe a quarter-sized ring of filling onto the flat side of one cookie. Top with its matching cookie, pressing gently until filling reaches the edges. Repeat for all remaining cookies. Let rest 10 minutes for filling to set.
• Serve candy cane cream cookies with cold milk. Best enjoyed same day; store leftovers in an airtight container at room temperature for up to 3 days.