Preheat your oven to 400°F and line a large baking sheet with parchment paper.
Toss the cubed butternut squash with 0.5 tablespoons of olive oil, sea salt, and black pepper on the prepared sheet.
Roast the squash for 25-30 minutes until the edges are caramelized and the flesh is fork-tender.
While the squash roasts, poach the chicken breast in simmering water for 12-15 minutes until fully cooked, then shred with two forks.
In a large pot, sauté the diced onion and minced garlic in the remaining 0.5 tablespoons of olive oil over medium heat until translucent.
Add the roasted squash, chicken bone broth, dried thyme, and cinnamon to the pot, simmering for 5 minutes to meld the flavors.
Use an immersion blender to puree the soup until completely smooth and creamy.
Fold the shredded chicken into the soup and serve warm.