Heat oven to 400°F and toss pumpkin, 2 tablespoons of olive oil, and a teaspoon of salt together on a baking sheet. Bake for 45 minutes, or until tender, flipping pumpkin half way.
Heat remaining olive oil over medium heat in a heavy-bottom pot. Sauté onion for 3 minutes until soft. Add minced garlic and roasted pumpkin, and continue to cook for another 3 minutes. Pour in broth and bring to a boil. Lower heat to a simmer and cook for 10 minutes.
Pour soup mixture into a blender and cover with blender top, leaving the small vent open to let hot steam escape. Cover with a kitchen towel and hold firmly to prevent hot liquid from escaping. Slowly start blender, steadily increasing speed until at full power. Remove kitchen towel from over top and blend until creamy. Pour blended soup back into warm pot. Whisk in cheese until melted, about 4 minutes. Pour soup back into blender and mix again until velvety smooth. Taste and season with more salt if desired. Serve hot with spicy, crispy garnish.
Heat 3 to 4 inches of canola oil over high heat in a heavy-bottom pot until temperature reaches 375°F.
Combine flour and salt in a large bowl.
Add chopped ingredients and flip 4 times to coat. Tap off excess flour, and use a stainless-steel spider strainer to place coated mixture into the hot oil.
Fry until golden brown, about 1 minute.