Prepare oven and pans
Preheat oven to 350°F (175°C). Spray two regular cupcake tins thoroughly with cooking spray.

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

Cream butter and sugars
In a large bowl, beat butter, granulated sugar, and brown sugar on medium-high speed for 2–3 minutes until light and fluffy.

Add eggs and vanilla
Reduce speed to low. Add eggs one at a time, mixing well after each. Add vanilla extract and mix until combined.

Combine dough
Gradually add dry ingredients to wet ingredients, mixing just until combined.

Portion dough
Scoop about 3 tablespoons of dough into each muffin cup.

Bake
Bake for 10–13 minutes, until edges are set and centers remain soft.

Form cookie cups
Immediately press a small jar or container into the center of each cookie to create a well.

Cool
Cool in pans for 10 minutes, gently twist to loosen, cool another 5 minutes, then transfer to a wire rack to cool completely.

Whip cream
In a cold bowl, whip heavy cream until stiff peaks form.

Make cheesecake filling
In another bowl, beat cream cheese, sugar, and peppermint extract until smooth.

Fold filling
Gently fold whipped cream into cream cheese mixture until fully combined.

Prepare piping bag
Paint two red stripes inside a piping bag fitted with a large round tip. Fill with peppermint cheesecake mixture.

Fill cookie cups
Pipe filling into cooled cookie cups.

Chill
Refrigerate for 1–2 hours until filling is set.

Garnish and serve
Sprinkle with chopped candy canes before serving.