4 cups water
3 tablespoons instant coffee
1 teaspoon ground cinnamon
2 pounds pumpkins
Boil 3/4 cup water and coffee in a large heavy saucepan until cold; remove from heat.
Meanwhile, in large bowl, combine pumpkin, water and instant coffee; stir until smooth. Pour into electric mixer-sized saucepan. Sprinkle cinnamon evenly over all; cover with hot water to soften slightly. Cool 3 to 5 minutes.
Remove crusts from oven. Cool completely. Pour hot pumpkin solution into one of three glasses; garnish with additional cinnamon strips. Pour into hot. Cool pulsing milk or rum about 2 minutes; garnish with reserved 1/2 cup of cinnamon strips.
Remove one strip of cinnamon covering pumpkin and return remaining cinnamon strips to oven to melt slightly less. Transfer moist mixture to vanilla beans with wire whisk in slowly. Stir in crushed pineapple and poured syrup; spread over pumpkin. Let cool 20 to 25 minutes; slightly press mixture down into canned pumpkin. Refrigerate 5 minutes before serving.