Chocolate Cookie Cups: Preheat your oven to 350°F (175°C). Spray two regular-sized cupcake tins 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 bowl, beat the butter and sugars on medium-high speed until light and fluffy, approximately 2-3 minutes. Reduce the speed and add the eggs one at a time, followed by the vanilla extract. Beat until combined.
Gradually add the flour mixture to the wet ingredients, mixing until just combined.
Using a large cookie scoop (about 3 tablespoons), scoop the dough into the prepared muffin tins.
Bake for 10-13 minutes, or until the cookie cups are mostly set but still soft in the middle.
Remove the tins from the oven and immediately use a small jar or container to press firmly down in the center of each cookie cup to create a well.
Cool the cookie cups in the pans for 10 minutes. Loosen each cookie cup by gently twisting it in the pan. Cool for an additional 5 minutes, then remove from the pan and transfer to a wire rack to cool completely.
Peppermint Cheesecake Filling: Whip the heavy cream until stiff peaks form (using a cold whisk and a cold bowl for best results).
In a separate bowl, beat the cream cheese, sugar, and peppermint extract until smooth.
Gently fold the whipped cream into the cream cheese mixture until fully combined.
Using a small food-safe paintbrush, paint two stripes of red color gel on the inside of a piping bag fitted with a large round tip. Carefully fill the piping bag with the cheesecake filling.
Pipe a swirl of the peppermint cheesecake filling into the cooled cookie cups. Refrigerate the filled cookie cups until the filling is set, approximately 1-2 hours.
Before serving, sprinkle the tops of the cookie cups with chopped candy canes if desired.
Serve chilled. These cookie cups are best enjoyed within 2-3 days. They can also be frozen for up to 4 weeks (without the chopped candy canes).