Cut pumpkin in half and remove and discard seeds. Leaving the pumpkin skin on, cut pumpkin into chunks roughly 4” x4” in size. No need to be precise here.
In a large heavy stockpot, place a layer of pumpkin skin side down. Cover with a layer of crushed piloncillo, 3 cinnamon sticks and 2 teaspoons of aniseed.
Place another layer of pumpkin, flesh side down (sandwiching the piloncillo, cinnamon, aniseed). Repeat, laying pumpkin skin side down, layering with piloncillo, cinnamon and aniseed until all the pumpkin fits into the pot. Note the pumpkin may be overflowing but will cook down quickly so pack it in.
Add 1/4 cup water, place pot over medium high heat and bring to a simmer. Once you see the steam rising from the pot, cover tightly, reduce heat to medium and cook until tender, approximately 1 ½ - 2 hours. The pumpkin releases quite a bit of liquid. This will mix with the spices and piloncillo and create a beautiful syrup which will transform the pumpkin flesh to a dark mahogany color and become almost translucent.
Using gloved hands, or slotted spoon, remove pieces of pumpkin from the pot on to a rimmed baking sheet. Allow to cool. Strain remaining liquid into a large measuring cup and reserve.
Scoop pumpkin flesh, removing the skin, into a large 7 qt saucepan. Mash the flesh and stir in one cup of the reserved pumpkin syrup. Simmer over medium low heat until most of the liquid is cooked out. Place in a bowl and cool/refrigerate until ready to use. Note, the pumpkin puree freezes well.
The remaining syrup is great served over vanilla ice cream or as a base for a pumpkin latte! Enjoy!