Preheat oven to 350°F. Spray muffin pans with nonstick cooking spray (I like using the kind with flour in it).
Make the cookies: Cream butter and sugar in the bowl of a stand mixer fitted with the paddle attachment. Beat in egg and both extracts. (Almond extract is optional, but adds amazing flavor!) Mix in baking soda, cream of tartar, and salt. Slowly mix in flour.
Place 2 tablespoon balls of dough into each muffin cup. Press the dough flat along the bottom and halfway up the sides of the muffin cup. It doesn’t need to be perfect because they’ll rise and you’ll need to reform them after baking. Bake for 8-10 minutes until they’re just turning golden brown (they taste better if you err on the side of under done).
When they’re hot from the oven, use the back of a glass (a shot glass or small juice glass is perfect) to press down in the center to re-form the cup shape. Spray the glass first with nonstick cooking spray to ensure it won’t stick. Let the cups cool, then remove from the pans (with the help of a butter knife, if needed).
Beat cream cheese until smooth with a hand mixer. Slowly beat in powdered sugar, salt and vanilla until smooth and creamy. Add coffee to taste and stir, then fold in the Cool Whip.
Spoon about 1 1/2 to 2 tablespoons of filling per cooled cookie cup. Dust with cocoa and serve.
Store loosely covered in the refrigerator for up to 3 days. Cups may be frozen for up to one month before filling.