01 -
Preheat the oven to 175°C (350°F). Spray two regular-sized cupcake tins thoroughly with cooking spray to prevent sticking.
02 -
Whisk together all-purpose flour, Dutch-processed cocoa powder, black cocoa powder, baking soda, and salt in a medium bowl. Set the mixture aside.
03 -
In a large mixing bowl, beat unsalted butter, granulated sugar, and light brown sugar on medium-high speed until light, fluffy, and well combined (about 2-3 minutes).
04 -
Reduce mixer speed to low and add eggs one at a time, followed by vanilla extract. Beat until fully incorporated.
05 -
Gradually add the flour mixture to the butter mixture. Mix until just combined, avoiding overmixing.
06 -
Using a large cookie scoop (approximately 3 tablespoons), portion cookie dough evenly into the prepared muffin tins.
07 -
Bake for 10 to 13 minutes, or until mostly set but soft in the center.
08 -
Immediately after removing from the oven, press down firmly into the center of each cookie cup using a small jar or container to create a well for the filling.
09 -
Cool cookie cups in the pans for 10 minutes. Twist slightly to loosen them, then transfer to a wire rack to cool completely.
10 -
Using a cold bowl and whisk, whip chilled heavy cream until stiff peaks form.
11 -
In a separate bowl, beat full-fat cream cheese, granulated sugar, and peppermint extract until smooth and creamy.
12 -
Gently fold whipped cream into the cream cheese mixture until fully combined and smooth.
13 -
Using a food-safe paintbrush, paint two decorative red stripes inside a piping bag fitted with a large round tip. Carefully fill the piping bag with peppermint cheesecake filling.
14 -
Pipe a generous swirl of cheesecake filling into each cooled cookie cup.
15 -
Refrigerate filled cookie cups for 1 to 2 hours, or until the filling is set.
16 -
Sprinkle chopped candy canes on top. Serve immediately or keep refrigerated for up to 2-3 days. To freeze, omit the candy cane topping and store for up to 4 weeks.