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Preheat the oven to 425°F. Line a baking sheet with parchment paper. Toss squash with 1 tablespoon oil, 1/4 teaspoon salt and pepper. Spread on the prepared pan and roast until tender and golden brown, about 25 minutes. (This can be done 24 hours ahead of time.)
Whisk the remaining 3 tablespoons oil, lemon juice, 1/2 teaspoon salt, cinnamon and pepper to taste in a small bowl.
Combine kale, squash, pecans, pomegranate seeds, sliced shallot and dressing in a large bowl up to an hour before serving. Add more salt if necessary and transfer to a serving platter.