4 medium red bell peppers
2 lb tomatoes
1 sweet onion (1/2 lb), chopped
2 garlic cloves, chopped
1 tsp Habanero Chile Powder
1/4 Cup plus 2 Tbsp Extra-Virgin Olive Oil, divided
1 3/4 Cups reduced-sodium chicken broth
Roast bell peppers on gas burners over high heat (or on a broiler pan about 2 inches from broiler element), turning with tongs, until skins are blackened, 10 to 12 minutes. Transfer to a bowl and cover with plastic wrap. Let stand 20 min. Peel peppers, then halve lengthwise, discarding stems and seeds.
Cut a shallow X in bottom of each tomato, then blanch them: dip each tomato in simmering water 20 seconds and transfer to an ice bath. Peel and coarsely chop, reserving tomatoes’ juices.
Cook onion, garlic, chiles, 1 tsp salt, and 1/4 tsp pepper in 2 Tbsp oil in a 3- to 4-quart heavy saucepan over medium heat, stirring occasionally, until softened and pale golden, about 8 minutes. Add tomatoes and their juices, bell peppers, broth, and 1/4 tsp salt and simmer, covered, until peppers are tender, about 5 minutes.
Purée soup in 2 or 3 batches in a blender (use caution when blending hot liquids – it can blow the lid off the blender and scald you), drizzling remaining 1/4 cup oil into first batch with motor run.
Allow soup to cool before serving. Can be made several hours ahead of time and chilled in the refrigerator.