Preheat the oven to 425F. Layer a large sheet pan with parchment paper (optional, makes clean-up easier).
Slice the tomatoes into 3-4 wedges, discarding the core. Slice the bell peppers into 4-5 wedges, discarding the center seeds and stem. Quarter the onions, also removing the core and pulling apart the layers of the onion to make 7-8 pieces total.
Spread the tomatoes, onion pieces, and red pepper slices out in an even layer on the sheet pan.
Sprinkle with olive oil, salt, and freshly ground black pepper, to taste. Use clean hands or a spatula to toss everything together. Drizzle the garlic cloves with oil, wrap in foil, and place on the sheet pan.
Transfer to the oven to roast on the middle rack at 425F for 30-35 minutes. It is ready when some pieces have char marks (they shouldn't be completely burned, just blackened in spots) and the tomatoes are reduced in size.
Transfer the roasted ingredients to a blender or food processor. Be careful not to overfill the blender. Add ½ cup water, vegetable bouillon, basil, and sugar.
Blend on medium speed for 1-2 minutes, until pureed. Vent the blender as needed to avoid steam buildup. Add the remaining ½ cup water, as needed.
Taste for salt and sugar. Garnish with extra basil and enjoy!
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Notes
Tomatoes: Any slicing tomato should work fine, just make sure to remove the core. I have made this recipe with half cherry tomatoes/half slicing tomatoes with success, though it yields a slightly less uniform texture.
Water/bouillon: 1 cup of vegetable broth can be used in place of the water and bouillon.
For creamier soup, use ½ cup whole milk in place of ½ cup water/broth.
Freezing: This tomato soup freezes well. If freezing in a glass jar, make sure to let the soup cool to room temp before freezing and leave at least one inch of space at the top of the jar. Let thaw overnight in the fridge when ready to reheat.
More garlic: For even more garlic flavor, roast an entire bulb of garlic. To do this, slice off the top ¼ inch of the bulb. Drizzle with olive oil then wrap in foil. A full bulb of garlic may take up to 45 minutes to roast. Squeeze the cloves out of the garlic when they are fully softened.