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Cut pork into large chunks. Place in a bowl. Add salt, pepper, cayenne, thyme, fennel seeds, rosemary, and shallots. Mix thoroughly and cover pork with parchment paper. Refrigerate to let flavors develop, 8 hours to overnight.
Preheat the oven to 350 degrees F (175 degrees C).
Add flour to pork and mix to coat. Heat oil in a skillet over medium-high heat. Cook pork in 2 batches until browned, about 3 minutes per side.
Insert the tip of a knife at a 45-degree angle into the top half of the pumpkin. Slowly cut all the way around to remove the 'lid'. Scrape seeds and fibers off the bottom of the lid and inside of the pumpkin using a large spoon or ice cream scoop.
Line the bottom of a baking pan with parchment paper and place pumpkin on top. Stuff the pumpkin with the browned pork; pour in cider. Cover with the top.
Bake in the preheated oven until pork is very tender, about 4 hours. Pour in a little more cider after a few hours in the oven, since a lot of it evaporates. Remove from the oven and let rest; brush pumpkin with some of the rendered fat from the bottom of the pan.
Scoop pork onto serving plates and cut out pieces of pumpkin to serve alongside. Combine remaining rendered fat with cooking liquid from inside the pumpkin. Let sauce rest for a few minutes so you can skim off most of the fat. Spoon sauce over the pork.