Preheat the oven to 425 degrees F, ensuring an oven rack is positioned in the top third of the oven. Line a baking sheet with parchment paper or foil and set aside. Gather and prep ingredients according to the Ingredients List.

Place the cubed delicata on the prepared baking sheet. Drizzle with 1 tablespoon of the oil, seasoning with salt and ground black pepper. Toss to combine and arrange in an even, flat layer. In a medium bowl, combine breadcrumbs, parmesan, garlic, and fresh herbs. Drizzle remaining olive oil over top and toss to combine. Sprinkle the mixture over the seasoned delicata squash, pressing to adhere.

Transfer to the oven and roast for 20-25 minutes, until the squash is tender and the parmesan crust is golden brown. In the last 3-4 minutes of roasting, add the pine nuts or chopped walnuts to toast. Remove from the oven and set aside.

Place the shredded or finely chopped kale in a large bowl, topping with the thinly sliced shallots and a pinch of salt. Squeeze the lemon juice over top and use your hands to massage the kale, working the lemon into the leaves until they’re vibrant green and wilty. Set aside.

To the massaged kale, add the squash croutons, toasted nuts, and shaved parmesan. Drizzle the Caesar dressing over top and toss to combine. Taste and season with additional salt and black pepper as needed. Serve immediately.