Prep the produce: Halve or quarter larger tomatoes. If using cherry tomatoes, leave them whole. Quarter the onion.
Peel the garlic (or leave skins on to prevent burning).
Toss with seasoning: In a bowl, combine tomatoes, onion, and garlic with olive oil, salt, pepper, oregano, sugar (if using), and red pepper flakes. Coat evenly.
Arrange in the air fryer: Place everything in the air fryer basket in a single layer if possible. A little overlap is fine, but avoid packing tightly.
Air fry: Cook at 400°F (200°C) for 14–18 minutes, shaking the basket once halfway.
You want blistered skins, caramelized edges on the onion, and softened garlic. If garlic looks too dark early, remove it and continue cooking the rest.
Blend the base: Transfer the roasted vegetables to a blender. If you left skins on the garlic, squeeze out the soft cloves and discard skins.
Add broth and tomato paste. Blend until smooth.
Adjust consistency: If it’s too thick, add more broth a splash at a time. For a rustic texture, pulse instead of fully blending.
Warm and finish: Pour the soup into a pot and bring to a gentle simmer for 3–5 minutes.
Stir in cream (if using). Taste and adjust salt, pepper, and sugar.
Serve: Ladle into bowls. Swirl with a little cream or olive oil, scatter torn basil, and add croutons or a grilled cheese on the side.