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1. Preheat oven to 400 degrees.
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2. Halve the tomatoes lengthwise. Chop the cauliflower into florets. Arrange tomatoes, halved side up, and cauliflower in a roasting pan (I split the tomatoes into one roasting pan and the cauliflower in another, as the tomatoes hog all the room). Drizzle the tops of the tomatoes with olive oil, and sprinkle a little salt and pepper over each one. Do the same with the cauliflower, then toss to coat. Chop the top off of the garlic head, drizzle with olive oil, and wrap tightly in aluminum foil.
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3. When the oven is ready, put the tomatoes, cauliflower, and garlic into the oven. Let them roast and do their thing for about an hour. After 30-40 minutes, give the cauliflower a toss for even browning. They might need to come out before the hour is up if they look done before then.
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4. Once the tomatoes are done and cooled, remove the peels (they should come right off, or at least, come off in just a few pieces), but be careful not to squeeze out their juices. We want those!
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5. Once the tomatoes are cooled and peeled, heat about a tablespoon of olive oil in a Dutch oven or big soup pot over medium-high heat. Add the onion and shallots and cook until softened, about 7 minutes. Add the oregano, basil, cayenne, paprika, coriander, and salt and pepper. Stir and let cook for about 2 minutes.
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6. Clear a spot on the bottom of the pot and add the butter. When it is melted, add the flour, and gently combine them into a paste. Let this cook for a minute, then mix it all together.
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7. Add the roasted garlic by squeezing each clove to release the soft roasted goodness (only add as much garlic as you can handle-I added the whole head!).
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8. Add the wine (or stock if you're not a total lout like me) and deglaze (use a spoon to break up the cooked-on delicious bits). Let this mixture cook down for a few minutes.
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9. Once the mixture has simmered a bit, add the roasted tomatoes and cauliflower. Use a spoon to break up the tomatoes a bit and let this simmer together for a few more minutes. Then turn off the heat.
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10. Using a blender, food processor, or my weapon of choice-an immersion blender-puree the mixture until it has reached your desired consistency. If you want a thinner soup, you could add some more broth to thin it out. I like it thicker. Season with more salt and pepper to taste. I found the seasonings added to the vegetables before roasting was adequate.
