Preheat the oven to 200° C (400°F).
Place the tomatoes on a baking tray lined up with parchment paper. Drizzle the tomatoes with olive oil, sugar and salt. Roast for approximately 20 minutes or until the tomatoes have browned slightly and their skins are slightly burst open.
To a small pan or skillet set at medium heat, add in the chile pasilla. Toast for approximately 5 minutes or until its skin turns brighter and has swollen up. Keep stirring at all times to prevent the chili from scorching. Set aside to cool off to touch.
Remove the stem, the pith and seeds from the chili. Ground up in a spice grinder. Set aside.
In a heavy bottomed base pot set at medium heat, warm up 1 tablespoon of vegetable oil. Incorporate the onion and cook for 5 minutes or until translucent. Add in the garlic and cook for 1 minute. Increase the heat to medium high and add the celery, carrot, and fennel. Sauté for approximately 5 minutes or until the vegetables develop some browning.
Lower the heat to medium, add in the remaining tablespoon of vegetable oil, the chili powder and tomato paste. Cook for 3 minutes stirring at all times. Incorporate the roasted tomatoes. Add in water, just enough to cover. Season with salt. Increase the heat to bring to a boil. Lower the heat, cover with lid, and simmer for approximately 25 minutes until the vegetables have softened up.
Add in the balsamic vinegar and herbs. Cook for 5 more minutes. Blend in a high speed blender until smooth. Might need to do in batches. Taste for salt.
Serve in a bowl. Sprinkle with some roasted pumpkin seeds or add in a spoonful of heavy cream and squeeze in a bit of lemon or lime juice, . Drizzle with some olive oil and cracked black pepper.