Take a handful of shortbread cookies and place them inside the ziploc bag and close tightly. With a rolling pin or meat tenderizer, smash the cookies into fine crumbs. Pour crumbs onto a small plate and set aside.
Rim the martini glass by brushing vanilla icing with a mini spatula around the rim of the glass. Then dip the rim of the glass in the crumbs; set aside.
Into the cocktail shaker, add all the ingredients with ice.
Shake vigorously to combine.
Strain into the martini glass.
For the garnish (optional): Carefully place the pumpkin stencil on top of the martini glass being careful not to get it wet from the drink. Sprinkle the pumpkin spice lightly over the stencil to cover the pumpkin. Then slowly pull up the stencil. Or just sprinkle a pinch of pumpkin spice on top if the stencil seems like too much work.
Enjoy and remember to drink responsibly!
Notes
For the garnish I printed out a small pumpkin stencil image and cut/traced out the image with an exacto knife. If you don’t want to go through all that trouble, you can find coffee stencils online that will work.