Preheat your oven to 400°F and line a baking sheet with parchment paper.
Toss the cubed butternut squash with 0.25 tbsp of the olive oil, sea salt, cinnamon, and nutmeg.
Roast the squash for 25-30 minutes until the edges are golden brown and the flesh is tender.
While the squash roasts, heat 0.25 tbsp of the olive oil in a skillet over medium heat and cook the chicken breast until the internal temperature reaches 165°F.
Remove the chicken from the pan, let it rest for 5 minutes, then shred it into bite-sized pieces using two forks.
In a large pot, heat the remaining 0.25 tbsp of olive oil and sauté the diced onion and minced garlic until translucent and fragrant.
Add the roasted squash and chicken bone broth to the pot, bringing the mixture to a gentle simmer.
Use an immersion blender to puree the soup until it reaches a velvety smooth consistency.
Stir the shredded chicken into the soup and season with black pepper.
Ladle the soup into bowls and garnish with the crunchy pepitas before serving.