• Preheat your oven to 400°F (200°C).

Prepare the Vegetables:

• Halve the tomatoes. Peel and slice onions into thin rounds.
• Toss the halved tomatoes in a large bowl with 1 tbsp. sugar, 1 tbsp. balsamic vinegar, and ½ tbsp. olive oil.
• Trim the fennel bulb, remove the core, and dice into small dice.
• Wrap the unpeeled garlic in foil.

Roast the Vegetables:

• Spread the tomatoes on a large baking sheet in a single layer. Add the wrapped garlic to the same tray.
• Roast for 30-40 minutes, until the tomatoes are fully collapsed and charred in spots. The garlic should be soft and golden.
• On a separate baking sheet, spread the onion slices in a single layer. Roast for 20 minutes, or until onions are tender and slightly charred.

Cook the Soup:

• Unwrap the garlic. Once it is cool to touch, squeeze garlic cloves out of their skins and mash them into a paste with a fork. Set aside.
• Heat the remaining olive oil in a large pot over medium heat. Add the diced fennel and sweat until translucent, about 5-7 minutes.
• Add the roasted tomatoes, onions, and garlic paste to the pot. If using dried savory, add it now. Also, add the remaining salt and sugar, and stir well.
• Pour in the water, stir the soup mixture again and bring it to a boil. Cover with a lid and simmer for 15 minutes.

Blend the Soup:

• Let the soup cool completely first.
• Use an immersion blender or transfer the mixture to a countertop blender. Blend until smooth.
• Pass the soup through a fine mesh strainer to remove any remaining bits (optional).
• Stir in the remaining balsamic vinegar.

Serve the Soup:

• Before serving, check the soup’s seasoning and consistency. Adjust with water, salt, or sugar if needed.
• Bring the soup to a boil, then lower the heat simmering for 10 minutes before serving it hot.

Preserve the Soup (Optional): To Can Tomato Soup:

• Pour the strained soup into sterilized canning jars, leaving appropriate headspace.
• Process in a boiling water bath canner or a steam canner, following the processing times provided in a table below.
• Let the jars cool completely before storing them in a pantry.

To Freeze Tomato Soup:

• Cool the soup completely before transferring it to airtight containers.
• Leave headspace for expansion during freezing.
• When ready to eat, thaw the soup overnight in the refrigerator.