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1
Preheat the oven to 300F.
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2
Divide tomatoes evenly between two rimmed baking sheets; drizzle with 1/4 cup olive oil, and sprinkle with 2 teaspoons salt.
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3
Bake until tomatoes begin to shrivel and juice on the pan has reduced, about 45 minutes; remove from oven.
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4
Lightly brush another rimmed baking sheet with olive oil; set aside.
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5
Raise oven temperature to 425F.
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6
In a medium saucepan over low heat, bring milk to a simmer.
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7
In the bowl of an electric mixer fitted with the paddle attachment, combine remaining 2 teaspoons salt, the flours, 3 tablespoons olive oil, and the yeast.
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8
Mix on low speed, gradually pouring in the hot milk until combined, scraping down the sides of the bowl as needed.
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9
Once combined, mix on medium speed for 1 minute.
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10
The dough will be very sticky.
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11
Transfer to the prepared baking sheet.
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12
Using lightly oiled hands, spread the dough evenly, making sure it fills the pan.
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13
Cover tightly with oiled plastic wrap and set in a warm place until the dough reaches just below the edge of the pan, about 30 minutes.
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14
Using your fingers, dimple the dough, in an uneven pattern, leaving 2 inches between each dimple.
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15
Evenly arrange half of the roasted tomatoes on the dough.
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16
Drizzle with 1/4 cup of olive oil, and sprinkle with salt.
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17
Bake, rotating sheet halfway through, until golden brown, about 20 minutes.
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18
Remove from the oven, and drizzle with the remaining 1/4 cup olive oil.
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19
Transfer to a wire rack to cool.
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20
Scatter the remaining tomatoes on top, then sprinkle with salt.
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21
Cut into slices with a serrated knife or pizza wheel.
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22
The bread can be kept, wrapped tightly in plastic, at room temperature for 2 to 3 days.
