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To roast the tomatoes and garlic bulb, see my Herb Roasted Tomatoes recipe.
In a medium-sized dutch oven pot over medium-high heat, add the olive oil. Once heated, add the chopped onions and sauté until translucent + fragrant, about 1-2 minutes. Remove from heat and add the sautéed onions in a high-powered blender along with the roasted tomatoes, garlic (once the insides are squeezed from the bulb), tomato paste, and vegetable stock. Blend on high-speed until everything is fully broken down and smooth. NOTE: Save a bit of roasted tomatoes as garnish, if desired.
In the same medium-sized dutch oven pot over medium-high heat, add the blended tomato mixture along with the heavy cream, salt, black pepper, smoked paprika, oregano, basil, parsley, red pepper flakes, and thyme, stirring everything together until combined.
Let everything boil for 1-2 minutes and then reduce heat to low to allow a simmer for another 5-6 minutes.
At this point, the soup should be thickened as it continues to simmer.
Remove from heat and serve immediately into prepared bowl(s), top with roasted tomatoes, and a side of grilled cheese, if desired.
Bon Appetit!