Preheat oven to 400 degrees and line a baking sheet with either parchment paper or a silpat.
Hack the kabocha squash in half and scoop out the seeds. Very carefully, hack the squash into thick pieces. Lay pieces on baking sheet and roast for 30-40 minutes until tender, flipping halfway through.
Let roasted squash cool then peel or slice off the green skin. Transfer squash to a food processor or blender and add the vegetable stock, salt, cayenne and brown sugar. Process until smooth.
Re-heat soup on the stove and garnish with fresh rosemary for serving.
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