In a small saucepan, whisk together the pumpkin puree, maple syrup, pumpkin pie spice, and milk over medium-low heat. Warm it gently for 3 to 4 minutes, whisking often, until the mixture is steaming and smooth. Keep whisking until there are no lumps of pumpkin left, and do not let it boil.

Remove the saucepan from the heat and let the pumpkin spice milk cool for about 5 minutes. It should be warm, not hot.

Drizzle about 2 tablespoons of caramel sauce down the inside walls of two tall glasses. Pour the cooled coffee evenly between the glasses, filling each one about a third of the way.

Slowly pour the warm pumpkin spice milk over the back of a spoon into each glass.

Add 2 scoops of vanilla ice cream to each glass. Top each float with whipped cream, extra caramel sauce, and a small dusting of pumpkin pie spice.

Serve immediately with a long spoon and a straw, then stir gently as you enjoy the layers.