Preheat oven to 400 degrees fahrenheit and line a large baking sheet with parchment paper.
Cut the squash or squashes in half with a sharp knife, then use a spoon to scoop out the seeds.
Place the squash flesh side down, skin side up on the baking sheet and roast for about 30 minutes. Cooking time will vary based on the size of your squash and your particular oven. You’ll know it’s ready when a fork easily slides into the flesh. The flesh side of the squash should have some browning or caramelization on the edges upon flipping over.
While the squash is cooking, cook the bacon. Using kitchen scissors, cut the bacon into small strips.
Add the bacon to a large soup pot and cook on medium-high heat until browned and crispy. When the bacon is cooked, transfer it to a paper towel lined plate. Reserve about 3 tablespoons of the bacon fat and reduce heat to medium. Discard any extra bacon fat.
Add the diced onion to the bacon fat and cook on medium heat for about 5 minutes.
Add the garlic and cook for another 3-5 minutes or until onions appear translucent and tender. Remove pot from heat and set aside.
Once the squash is done cooking, remove from the oven and allow to cool. This may take up to 30 minutes. Once cool enough to handle, use a spoon to remove the flesh from the squash. Don't worry if small pieces of the green skin remain on the flesh. The skin is soft and edible.
Add the squash, can of coconut milk, 1 cup of the chicken broth and the onions and garlic to a blender. Depending on the size of your blender, you may need to add less liquid if it reaches the capacity. Blend on high until the soup reaches a velvety smooth consistency.
Pour the soup back into the large soup pot and add remaining chicken broth, salt and pepper. Turn heat to medium until the soup reaches a light simmer, about 4-5 minutes.
Ladle soup into bowls and top with crumbled bacon and pumpkin seeds.