These Chocolate Peppermint Cookie Cups are the perfect make-ahead treat for the holidays. Dark chocolate cookies filled with a whipped peppermint cheesecake and topped with crushed candy canes!
Preheat oven to 350°. Spray two regular sized cupcake tins with cooking spray.
Whisk together flour, cocoa powders, baking soda, and salt. Set aside.
Beat butter and sugars on med-high until light and fluffy (approx. 2-3mins). Reduce speed and add eggs one at a time and vanilla. Beat until combined. Add flour mixture and mix until just combined.
Using a large cookie scoop (3 Tbsp) scoop dough into muffin tins.
Bake for approx. 10-13mins or until mostly set, but still soft in the middle.
Remove from oven and immediately use a small jar or container to press firmly down in the center to create a well.
Cool in pans for 10mins, loosen each slightly by twisting it in the pan. Cool for 5 more minutes then remove from pan and cool completely on a wire rack.
Peppermint Cheesecake Filling:
Whip heavy cream until stiff peaks (ideally with a cold whisk and in a cold bowl).
In a separate bowl, beat cream cheese, sugar, and peppermint extract until smooth.
Add whipped cream into cream cheese mixture and beat until combined.
Using a small food-safe paintbrush, paint two stripes on the inside of a piping bag fitted with a large round tip. Carefully fill with cheesecake filling.
Pipe a swirl into cooled cookie cups and refrigerate until set (approx. 1-2 hours).
Sprinkle with chopped candy canes if desired.
Serve chilled and eat within 2-3 days. Or freeze for up to 4 weeks (without chopped candy cane).