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

In a large mixing bowl, whisk together the all-purpose flour, Dutch-processed cocoa powder, black cocoa powder, baking soda, and salt.

In another bowl, cream the unsalted butter, granulated sugar, and light brown sugar until light and fluffy. Add eggs one at a time, followed by vanilla extract.

Gradually add the dry ingredients to the creamed mixture and mix until just combined.

Scoop the dough into the muffin tin, filling each cup about two-thirds full. Flatten slightly and bake for 10-13 minutes.

Immediately press a jar or small glass into the center of each cookie cup to create wells.

Allow the cookie cups to cool in the pan for about 10 minutes, then transfer to a wire rack.

In a chilled bowl, whip the heavy whipping cream until stiff peaks form. Beat softened cream cheese with granulated sugar until smooth. Fold in whipped cream and Oreo crumbs.

Using a piping bag, fill the cooled cookie cups with the cheesecake filling and refrigerate for 1-2 hours.

After chilling, serve and garnish with additional Oreo crumbs or whipped cream.