Preheat your oven to 350°F (175°C) and spray two regular-sized cupcake tins thoroughly with cooking spray.

In a medium bowl, whisk together the flour, Dutch-processed cocoa powder, black cocoa powder, baking soda, and salt. Set aside.

In a large mixing bowl, beat the butter, granulated sugar, and light brown sugar on medium-high speed until light and fluffy, about 2 to 3 minutes.

Reduce mixer speed to low and add eggs one at a time, followed by the vanilla extract. Beat until fully incorporated.

Gradually add the flour mixture to the butter mixture and mix until just combined.

Using a large cookie scoop, portion the dough into the prepared muffin tins.

Bake cookie cups for about 10 to 13 minutes until mostly set but still soft in the centers.

Immediately after removing from the oven, press down firmly in the center of each cookie cup to create a well.

Allow cookies to cool in the pans for 10 minutes, then transfer to a wire rack to cool completely.

Whip the chilled heavy cream in a cold bowl until stiff peaks form.

In a separate bowl, beat the cream cheese, granulated sugar, and peppermint extract until smooth and creamy.

Gently fold the whipped cream into the cream cheese mixture until fully combined.

Fill a piping bag fitted with a large round tip decorated with red stripes and fill with cheesecake mixture.

Pipe the filling into each cooled cookie cup and refrigerate for 1 to 2 hours or until set.

Sprinkle chopped candy canes on top before serving.