Chocolate Pumpkin Cookie Cups

Ingredients

*Spoon & Sweep method: Use a spoon to fill measuring cup with flour until required amount is obtained. Scooping measuring cup directly into flour bag will firmly pack flour resulting in too much flour required for recipe.

In medium bowl, whisk together all ingredients for pudding. Cover and refrigerate a minimum 4 hours, preferably overnight.
Preheat oven to 350°F. Grease a mini muffin tin with baking spray and set aside.
Cream together sugar and butter. Add egg and vanilla extract and mix to combine.
In a separate bowl, sift flour, cocoa powder, salt, baking soda, and cream of tartar together. Add into wet ingredients slowly, until dough forms.
Roll 1 1/2 tablespoon-sized balls of dough and place into muffin tin, creating a well with your fingers. Bake for 13-15 minutes.
As soon as cookies come out of oven, use a handle of wooden spoon, pestle or muddler and press center down, creating a well in cookie cups. Cool 10 minutes in tin then move cookies onto a cooling rack to cool completely.
Place pudding in piping bag and fill cookie cups.
Place whipping cream in bowl and beat with a whisk attachment. Whip on medium until soft peaks form. Add in powdered sugar and vanilla, and whip on medium to medium-high for stiff peaks.
Place sweetened whipped cream in a piping bag fitted with small open star piping tip and pipe onto pumpkin cookie cups.
Serve immediately or store in the refrigerator.