Preheat your oven to 400°F and line a large baking sheet with parchment paper.
Place the cubed butternut squash, diced apple, and chicken breast on the sheet, drizzling with olive oil, sea salt, black pepper, and cinnamon.
Roast for 25-30 minutes until the squash is fork-tender and the chicken is fully cooked to an internal temperature of 165°F.
While roasting, sauté the diced onion and minced garlic in a large pot over medium heat until translucent and fragrant.
Remove the chicken from the tray and shred it into bite-sized pieces using two forks, then set aside.
Add the roasted squash, apples, and fresh sage to the pot with the onions, then pour in the chicken bone broth.
Use an immersion blender to puree the soup until it reaches a velvety smooth consistency.
Stir the shredded chicken back into the soup and simmer for 5 minutes to meld the flavors before serving hot.