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1
Place a sheet pan on the middle rack in the oven and preheat the oven to 400°F.
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2
Place the garlic cloves, onion, and Italian seasoning in a bowl and toss with 2 tablespoons of olive oil.
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3
Core the tomatoes and cut them in half.
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4
Carefully remove the hot sheet pan from the oven. Drizzle about 3 tablespoons of olive oil on the sheet pan and tilt and swirl to disperse.
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5
Place the tomatoes flesh side down on the sheet pan. Add the onion mixture around the tomatoes.
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6
Sprinkle with a heavy pinch of salt and a few grinds of pepper.
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7
Bake for about 30-35 minutes, or until the tomato skins are wrinkly and the garlic cloves are soft.
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8
Remove the sheet pan from the oven. Let cool for 5 minutes.
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9
Carefully pull the skins from the tomatoes, leaving the tomatoes on the sheet pan.
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10
Remove the skins from the garlic cloves and return to the sheet pan.
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11
Sprinkle with sugar, balsamic vinegar, and a bit more salt and pepper. Mash the tomatoes a fork and stir to combine.
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12
Bake for another 25-30 minutes until thickened and hot. Let cool 10 minutes.
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13
Transfer to a blender or food processor, along with the basil leaves, and blend until smooth.
