Preheat your oven to 350°F (175°C) and grease a cupcake tin with cooking spray.

In a medium bowl, combine all-purpose flour, black cocoa powder, baking soda, and salt. Whisk until fully blended.

In a large mixing bowl, cream together unsalted butter, granulated sugar, and brown sugar until light and fluffy, about 3-5 minutes.

Incorporate the eggs one at a time and mix well, then add vanilla extract until blended.

Gradually fold the dry ingredient mixture into the wet ingredients until the dough forms.

Scoop the dough into each cavity of the prepared cupcake tin, filling each about two-thirds full, and bake for 10-13 minutes.

Immediately after baking, press the bottom of a small container or shot glass into the center of each cookie.

Allow the cookie cups to cool in the tin for about 10 minutes before transferring to a wire rack.

Whip the heavy cream in a bowl until stiff peaks form. In another bowl, beat the cream cheese with powdered sugar and peppermint extract until smooth.

Gently fold the whipped cream into the cream cheese mixture until no streaks remain, then pipe the filling into each cookie cup.

Refrigerate the filled cookie cups for 1-2 hours to set the filling, then garnish with chopped candy canes before serving.

Serve your Chocolate Peppermint Cookie Cups chilled or at room temperature.