Prepare your classic brown sugar pearls by stovetop or Instant Pot, as directed on the bag. Soak in a brown sugar or honey syrup (optional) and set aside.
Brew your coffee. 2 espresso shots or ½ cup strong brewed coffee. Cool and set aside.
Add all remaining ingredients to a blender and pulse until smooth. It should look like pumpkin milk.
Fill a glass halfway with ice cubes.
Generously scoop your boba over the ice cubes.
Pour the coffee over the ice cubes and top with the pumpkin milk.
Top with whipped cream and a sprinkle of pumpkin pie spice (optional)