Gather and prep all ingredients according to the ingredient list to have ready and organized for use.
Preheat oven to 400°, and line a baking sheet with foil.
Place the split chicken breasts on the baking sheet, drizzle with a little oil, and sprinkle with salt and pepper.
Cut the tops off of the heads of garlic, drizzle each head with oil, plus a pinch of salt and pepper, wrap each in foil, and place on the baking sheet next to the chicken.
Roast the chicken and garlic for 45 to 50 minutes, then allow to cool until handled.
Shred the cooled chicken and set it aside; squeeze the roasted garlic from its paper and make it into a paste.
Place a medium-large soup pot over medium heat, drizzle in oil and butter. Once melted, add in the onion and sweat for about 3 to 4 minutes until translucent.
Add the roasted garlic paste to the onion and stir to combine.
Add the diced carrots, parsnips, celery, and butternut squash, then incorporate with Italian seasoning, salt, pepper, and red pepper flakes.
Stir in the tomato paste and allow to cook with the vegetables for 1 to 2 minutes.
Add in the chicken stock and stir, followed by the parmesan rind if using. Bring to a vigorous simmer, reduce heat, cover, and simmer for about 20 to 22 minutes until veggies are tender.
Prepare gnocchi according to package instructions if using, then set aside and keep warm.
Once the soup has simmered, turn off the heat, remove the parmesan rind if used, and stir in the kale allowing it to wilt.
Finish by adding the shredded chicken, basil, and parsley. Check for additional salt/pepper if needed.
Serve by adding about ¼ cup of cooked gnocchi to a bowl, ladle soup over top, and garnish with grated parmesan if desired.