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

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

In a large mixing bowl, beat the unsalted butter, granulated sugar, and light brown sugar until light and fluffy (about 2-3 minutes).

Reduce speed to low, add eggs one at a time and mix in the vanilla extract until fully incorporated.

Gradually add the flour mixture until just combined.

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

Bake for 10-13 minutes until mostly set but soft in the centers.

Press down in the center of each cookie cup to create a well using a small jar.

Cool in the pans for 10 minutes, then transfer to a wire rack.

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

In another bowl, combine cream cheese, sugar, and peppermint extract, beating until smooth.

Fold the whipped cream into the cream cheese mixture until fully combined.

Prepare a piping bag painted with red gel color and fill it with the peppermint cheesecake filling.

Pipe a swirl of filling into each cooled cookie cup.

Refrigerate filled cookie cups for 1-2 hours until the filling is set.

Sprinkle with chopped candy canes just before serving.