Preheat the oven to 400 degrees F.
On a sheet pan, toss the squash with 1 tablespoon olive oil, Italian seasonings, red pepper flakes, 1/2 teaspoon kosher salt and 1/4 teaspoon black pepper. Spread them in a single layer across the pan.
Roast the squash for 25-30 minutes until it is lightly browned on the edges and tender in the middle.
Cook the orzo in salted boiling water until al dente according to package instructions. Drain and rinse with cold water in a colander or strainer.
Heat 3 tablespoons olive oil in a large skillet or sauté pan over medium heat. Toast the breadcrumbs, stirring frequently, until they turn golden brown, about 2-3 minutes. Add the garlic, 1/2 teaspoon kosher salt and 1/4 teaspoon black pepper. Continue cooking for 30 seconds until fragrant.
Add the kale and lemon juice and sauté until the kale has wilted, about 2-3 minutes.
Stir the orzo, roasted squash, parmesan and parsley into the kale and allow a couple minutes to combine everything and for it to warm.
Garnish with additional cheese and herbs when you serve it.