Preheat oven to 400 degrees F. Cut squash in half, lengthwise and scoop out seeds.
Drizzle flesh with olive oil and cinnamon. Place flesh down on baking sheet on a baking sheet covered in parchment paper.
Roast until squash is soft tender when pricked with a fork, about 40 minutes. Once you can handle the squash, carefully scoop out the inside flesh and scoop into a bowl. Be careful not to burn yourself!
While the squash roasts, put a medium saucepan with water on the stove to boil the potatoes and apple. Add the potatoes to boiling water. Boil for 20 minutes or until potatoes are nice and soft. Add the apple into the water with the potatoes in the last 10 minutes. Drain and set aside.
Heat 2 tablespoon of olive oil in large saucepan on medium heat. Add shallots, ginger and garlic. Sprinkle with Kosher salt. Cook for about 2 minutes, stirring frequently.
Then to the shallots and garlic, add the boiled potatoes, apple, scooped out squash and pumpkin spice mix. Cook for 2 minutes, stirring things up and smashing the potatoes down with a wooden spoon. Add broth and coconut milk. Stir together.
Let simmer for about 10 minutes on medium heat.
Then puree the soup with a hand immersion blender or blender. Do it in batches to help reduce spillage if using a blender. Be careful not to burn yourself!
Add in the maple syrup at the end with some fresh group pepper and give a final stir before serving.