Crust: In food processor, pulse cookies until mostly crumbled. Add butter and pulse until completely blended (fine crumbs).

Using a small spoon, gently pack about 1 ½ teaspoons of the crumbled cookie mixture into the bottom of each shot glass (30 shot glasses total). Reserve any extra crumbs to sprinkle on top.

Whipped Cream: Combine heavy cream, 1 cup powdered sugar, and 2 teaspoons vanilla extract in a large bowl. Use an electric mixer to beat until mixture is thick and billowy and stiff peaks have formed.

Divide whipped cream in half (approximate is fine), you will need half for the filling and half for the topping. Set both aside for now.

Pumpkin Pie Cheesecake Layer: Using an electric mixer or stand mixer, beat together cream cheese, pumpkin puree, and brown sugar until mixture is smooth and well-combined.

Gradually stir in powdered sugar until combined.

Add in pumpkin spice and vanilla extract and stir well.

Take one half of your reserved whipped cream and carefully fold it into the pumpkin mixture until smooth. You could do this with an electric mixer on low speed but I usually do this part by hand.

Pipe filling into prepared shot glasses, filling nearly to the brim. Pipe or dollop your remaining half of whipped cream evenly overtop the dessert shooters. If you reserved any cookie crumbs, sprinkle these over the whipped cream for decoration if desired.

While these desserts may be served immediately, the filling will be quite soft and I recommend chilling in the refrigerator in an airtight container for at least 4 hours before serving.