Make the syrup. In a small saucepot, whisk the pumpkin, sugar, brown sugar, pumpkin pie spice, and water until combined. Bring to a simmer over medium heat and warm for 5-10 minutes until the granules dissolve and the sauce thickens. For a thicker syrup, leave on the burner longer. Remove from heat and whisk in the vanilla.
In a separate sauce pot, warm the milk until steaming (but not boiling else you've scalded it oh no), about 5-8 minutes.
Measure about 2-3 tablespoons of the pumpkin syrup (use to taste) into a cute mug. Pull your espresso shots overtop, then add the milk. Garnish with whipped cream and cinnamon, as desired.
Notes
*Espresso alternative: If you don't have an espresso machine, use 1/2 cup strong brewed coffee instead.*Maple whipped cream: Combine 1 cup heavy whipping cream with 2 tablespoons maple syrup and 1 teaspoon vanilla. Whip on high speed for 4-5 minutes until firm peaks form.