For the Chocolate Cookie Cups:
Get ready! Preheat your oven to 350°F (175°C). Lightly spray two regular muffin tins with cooking spray to prevent sticking.
In a medium bowl, whisk together the flour, both cocoa powders, baking soda, and salt until well combined. Set this dry mixture aside.
In a larger bowl, beat the softened butter and both sugars together with an electric mixer on medium-high speed until the mixture is light and fluffy (about 2-3 minutes). Reduce the speed, then add the eggs one at a time, followed by the vanilla extract, beating just until everything is combined.
Gradually add the dry flour mixture to the wet ingredients, mixing on low speed until just combined. Be careful not to overmix!
Use a large cookie scoop (about 3 tablespoons) to place generous mounds of dough into each muffin cup.
Bake for about 10-13 minutes, or until the edges are set but the centers still look a little soft. This keeps them wonderfully tender!
Once out of the oven, immediately use the back of a small jar or a round tool to gently press down in the center of each cookie cup, creating a perfect well for the filling. Let them cool in the pans for 10 minutes, then carefully twist each one to loosen. After 5 more minutes, remove them and let them cool completely on a wire rack.
For the Peppermint Cheesecake Filling:
In a chilled bowl with a cold whisk (this helps!), whip the heavy cream until stiff peaks form. Set aside.
In another bowl, beat the softened cream cheese, sugar, and peppermint extract until smooth and creamy. Gently fold the whipped cream into the cream cheese mixture until just combined and fluffy.
If you want that festive candy cane swirl, use a small, food-safe paintbrush to paint two red stripes inside a piping bag fitted with a large round tip. Carefully spoon the cheesecake filling into the bag.
Pipe a beautiful swirl of filling into each cooled cookie cup. Refrigerate for 1-2 hours until the filling is nicely set.
Just before serving, sprinkle with crushed candy canes for that extra holiday sparkle!