Serve with a salad or a grilled cheese for dunking.
Line a large rimmed baking sheet with parchment paper.
Toss cherry tomatoes and shallots with 1 tablespoon oil and oregano on the prepared baking sheet.

Photo: Photographer: Jen Causey; Food Stylist: Ali Ramee; Prop Stylist: Claire Spollen
Roast until the tomatoes burst and the shallots are tender, about 20 minutes.
Do not turn the oven off.
Place a clean towel over the opening.
Process until smooth, about 30 seconds.
Pour into a large nonreactive saucepan.
Bring the tomato mixture to a simmer over medium heat.
Cook, stirring occasionally, until slightly thickened, 10 to 15 minutes.
Bake until toasted and crisp, about 15 minutes.
Divide the soup among 4 bowls; drizzle evenly with the remaining 1 tablespoon oil.
Top with croutons and garnish with basil, if desired.
To make ahead
Cover and refrigerate for up to 3 days.
- Daily Values (DVs) are the recommended amounts of nutrients to consume each day.
(-) Information is not currently available for this nutrient.