Drizzle one tablespoon of Garlic Infused EVOO in the bottom of a roasting pan. Set a strainer or colander over a bowl, and gently squeeze the juice out of each tomato. Let the juice collect in the bowl, and place the tomatoes in the pan. Arrange them so that there is a minimal amount of overlapping. Once all the tomatoes are in the pan, drizzle them with the other tablespoon of Garlic Infused EVOO, then season with salt and pepper (adjust the amount of salt you use according to whether or not the canned tomatoes are already salted). Arrange the sprigs of thyme over the tomatoes. Set aside the reserved tomato juice.
Wrap the garlic cloves in a tight foil packet with a few drops of olive oil inside. Add the foil packet of garlic to the pan. Roast until the tomatoes start to brown and the garlic is tender, about 25 min. Let everything cool slightly. Once the garlic is cool enough to handle, squeeze the cloves out of the skin. Remove any wiry thyme stems from the tomatoes.
Heat one tablespoon of Varietal EVOO in a large saucepan over medium heat. Saute the shallot until translucent and fragrant, about 3-5 minutes. Add the tomatoes, garlic, crushed red pepper, two cups of reserved tomato juice and two cups of broth. Bring everything to a boil, and then let simmer for 25 minutes.
Remove from the heat, and using an immersion blender (or transferring everything to an actual blender), puree the soup until it has a consistency to your liking. Adjust seasonings to taste and serve in bowls with a drizzle of Varietal EVOO (or more Garlic Infused EVOO if you can't get enough).
This soup freezes well and is, of course, amazing with grilled cheese (or a grilled cheese lid if you're fancy).
You can substitute the Garlic Infused EVOO for any of the following!