Mix 2 teaspoons of coconut sugar with 1 teaspoon of cinnamon. Sprinkle this mixture on top of the halved pears.
Heat a skillet with the olive oil over medium heat. Swirl the oil around to coat the entire skillet. Place the pears on top of the skillet, cut side down. Let it cook for about 4-5 minutes, or until the pears get a deep golden brown color.
While the pears are cooking, mix the rest of the coconut sugar, water, and vanilla extract together.
When the pears are golden brown, turn them over, pour in the sugar water, and cook covered for a few minutes. When the liquids boil, turn off the heat.
Prepare the pumpkin sauce. Mix the pumpkin puree, 1 teaspoon of cinnamon, almond milk, maple syrup, ginger, and nutmeg together in a small bowl.
Serve the pears with the pumpkin sauce. Drizzle any remaining vanilla syrup from the skillet onto the pears. Top the pears with chopped pecans and cranberries if you like. Best served hot!