Preheat oven to 400F.
Place chicken thighs skin side up on a baking sheet. Sprinkle with salt and pepper. Bake for 35 minutes, until chicken skin is light brown and just starting to get crispy.
Let chicken thighs cool for 10 minutes so you can remove the skin by slipping them off the thigh meat. Set aside chicken thighs to use later.
Place chicken crackling exterior skin side up on a baking sheet and return to oven for 10-15 more minutes. Skin should be dark brown and crispy before removing from the oven.
In a large dutch oven, add diced squash and chicken stock. Bring to a boil and cook for 20 minutes covered with a lid.
Add sliced onion, potato, garlic, thyme sprigs, carrots, and Scotch Bonnet pepper. Simmer on low heat while making the dumplings.
In a large mixing bowl, add 1 cup flour and a little bit of water to make dough. Lightly knead the dough until the consistency is firm and not too sticky. Roll the dough in between the palm of your hands to form spherical dumplings.
Drop the dumplings into your homemade Jamaican Soup and stir.
Add the Allspice berries, corn and bone-in chicken thighs. Cook for another 20-25 minutes.
Remove the spicy pepper and chicken bones from the pot and discard.
Garnish with fresh cilantro and chicken skin cracker. Serve in large soup bowls.