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Preheat the oven to 400 degrees F. Line a rimmed baking sheet with parchment. Bring a large pot of salted water to a boil.
Toss the butternut squash with 2 tablespoons of the olive oil, 1/2 teaspoon salt and 1/4 teaspoon pepper. Spread the squash into a single layer on the prepared baking sheet. Bake until the squash is tender, 15 to 20 minutes. Set aside to cool.
While the squash is cooking, cook the orzo in the boiling water according to the package instructions. Drain, rinse with cold water and set aside.
Meanwhile, whisk together the vinegar, honey, lemon zest and juice, 1/2 teaspoon each salt and pepper and the remaining 4 tablespoons olive oil in a large bowl. Toss in the orzo, squash, cranberries, almonds, dill and scallions until everything is coated. Serve in a large bowl, or transfer to 8-ounce mason jars with lids for easy traveling. Serve at room temperature.
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