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1
Preheat the oven to 375 degrees F.
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2
Heat a large cast iron skillet and add the canola oil.
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3
When the oil begins to smoke lightly, add the tomatoes in a single layer.
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4
Season with salt, to taste, and add the sugar.
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5
You want to blister the skin slightly, drawing out water from the tomatoes, to intensify their flavor.
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6
Add the vermouth.
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7
Continue cooking on low heat.
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8
In a soup pot, heat 1 tablespoon of the olive oil and add the garlic, shallots, and red pepper flakes.
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9
Season with salt and pepper.
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10
Add the oregano and stir to blend.
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11
Allow to cook, over low heat, until the shallots and garlic become tender and translucent, 3 to 5 minutes.
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12
Add the canned tomatoes and the water.
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13
Turn the heat down to medium and cook until the tomato flesh starts to lose shape, 12 to 15 minutes.
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14
At this point, the soup should be mushy and blender-ready.
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15
If there are still some hard pieces, add a little more water and cook for a few additional minutes.
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16
Taste for seasoning.
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17
Put about half of the tomato soup in the blender and puree until smooth.
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18
Next, puree the roasted Roma tomatoes in the blender until smooth, adding the remaining olive oil through the top in a slow, steady stream.
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19
Taste for seasoning.
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20
Add both back to the remaining chunky soup.
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21
Taste for seasoning.
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22
On a flat surface, slice bread into 4 by 1/2-inch thick slices.
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23
Tear each piece into a freeform shape that sits nicely across the top of your soup bowls (the nice torn edges will get super crispy).
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24
Set on a sheet tray and toast in oven for 4 to 5 minutes until lightly golden and crispy.
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25
Ladle the soup into crocks or small oven-proof bowls.
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26
Top with 1 piece of toasted bread per bowl.
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27
Finish with some shredded mozzarella and broil until golden brown, about 2 minutes.
