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Step 1
Arrange a rack in the middle of the oven and heat to 425°F.
Step 2
Place the squash, onion, garlic, 2 tablespoons of the oil, a big pinch of salt, and a few grinds of black pepper in a large bowl and toss to combine. Transfer to a rimmed baking sheet and spread into an even layer (reserve the bowl). Roast until the vegetables are tender and very caramelized, 25 to 30 minutes.
Step 3
Meanwhile, place the lentils and bay leaves in a medium saucepan. Add enough water to cover the lentils by 1 inch. Bring to a boil, then reduce heat and simmer until just tender, 15 to 20 minutes. Drain the lentils and discard the bay leaves. Return the lentils to the pan and stir in 1/2 teaspoon of salt. Taste and season with more salt as needed.
Step 4
Once the vegetables are roasted, remove the garlic cloves and set aside until they are cool enough to handle, about 5 minutes. Squeeze the roasted cloves out of their paper into the bowl used to toss the roasted vegetables and mash them with a fork. Add the remaining 6 tablespoons of oil, vinegar, mustard, a pinch of salt, and a few grinds of black pepper to the bowl and whisk to combine.
Step 5
While the lentils are still warm, add them to the dressing. Add the kale and toss until well coated. Add the roasted vegetables, pecans, and raisins and toss to combine. Taste and season with salt and pepper as needed. Just before serving, toss in the parsley. Transfer the salad to a large platter and serve warm or at room temperature.