Preheat oven to 400F. Halve the squash lengthwise, and scoop out the seeds. Rub all sides of the squash with olive oil. Season the flesh side with Chinese five-spice powder and salt. Peel, halve, and core the apples, seasoning them with five-spice powder and salt as well. Roast squash and apples in oven, cut sides up, for 30 minutes. After 30 minutes, flip the squash and apples so the cut sides are down and roast for another 30 minutes or until tender to the touch.
Remove squash and apples from oven and let cool slightly. Scoop out the flesh of the squash and discard skin. Pass roasted squash and apples through a food mill.
Place pureed squash and apples in a pot over low heat. Whisk in butter, a pinch of Chinese five-spice powder, and molasses until well incorporated. Season with salt and keep warm to serve. Garnish with pepitas and chives.
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