Halve the butternut squash, then remove the seeds. Rub with some of the olive oil (about 1-2 teaspoons) and sprinkle with smoked paprika, cinnamon, pepper and 1/2 teaspoon of salt. Place in the oven and roast until very tender, about 1 hour. Remove and let cool slightly. Then scoop out the tender squash flesh and place in a bowl, discarding the skin.
Heat the remaining olive oil in a stock pot and cook over medium heat. Add the onion and remaining 3/4 teaspoon salt and cook until onion is very tender, about 10 minutes.
Add the garlic and cook another minute, taking care not to burn. Add in the tomatoes with their juices, the squash and 1 cup broth. Simmer for 20 minutes, stirring occassionally.
Remove from heat and let cool slightly, then add to a blender (or use an immersion blender) and puree until smooth. Return back to the pot and simmer for another few minutes until hot, then divide into bowls and serve.