2) To 3 of the squash halves, add a peeled shallot and to the other 3 add 2 garlic cloves on each. Drizzle with 2 tbsp olive oil and season with 1 tbsp each of the salt and pepper.
3) Roast in the hot oven until very tender and starting to caramelise and collapse, approximately 1 hour. Remove from oven and when cool enough to handle, remove the squash from the skin. Reserve the roasted shallots and garlic with the squash. This can be done ahead.
4) In a large Dutch oven, heat 1 tbsp olive oil and 2 tbsp butter over medium-high heat and when the butter is starting to foam, add the raw diced shallots and saute until they are starting to caramelise, about 5 to 6 mins. Deglaze with 120ml of the chicken stock and stir to remove any fond.
5) Reduce the heat to medium-low and add in the reserved squash, roasted shallots and garlic and then the remaining chicken stock. Stir to combine, then puree with a stick blender. The mixture will be very thick. Add in the cayenne, white pepper and the herbs. Stir in the cream and Worcestershire sauce and heat slowly over medium-low heat.
6) When the mixture comes to a slow simmer, mix again with the stick blender and stir in 25g of the Parmesan, then turn the heat to low. Serve with freshly ground black pepper, a nice drizzle of extra-virgin olive oil and a light sprinkle of the remaining Parmesan. Ladle into soup bowls and serve.